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Lake Morey Resort - Fairlee, Vermont
White Elephant Hotel on Nantucket, MA - Waterfront Luxury - Click here to book now!

Massachusetts hotels, inns, and resorts welcome your family

Family friendly hotels, inns and other lodgings are abundant in Massachusetts. Family friendly lodgings and accommodations can be found in every price range and in every corner of the state: from city centers like Boston, to the beaches of Cape Cod and Nantucket and Martha’s Vineyard, to the mountains, farmland, and small towns of Central Mass. and the Berkshire Mountains. Family friendly hotels and motels generally offer the convenience of restaurants and swimming pools, as well as close proximity to family attractions, beaches and water sports, skiing, hiking, and other fun things to do for families.
Kids in the Pool - The Nantucket Hotel & Resort - Nantucket, MA
The Nantucket Hotel & Resort

77 Easton Street Nantucket, MA, 02554 Phone: 508-228-4747 Toll-Free: 866-807-6011

Our Grand, Award-Winning Nantucket resort makes family fun a specialty

The Nantucket Hotel & Resort is open for the 2020 season! New this summer. Private experiences, private dining, and fun family activities - click here for more info.

Families love their stays at the award-winning Nantucket Hotel + Resort, and it’s no wonder: Activities at our resort include a complimentary Kids’ Club activities program; antique fire truck rides; library and complimentary DVD rentals; Concierge Services; a game room; shuttles to-and-from Nantucket’s popular beaches during the in-season; a fun, make-your-own S’mores program at our Breeze restaurant, complimentary outdoor heated pools; and more. With our resort as your home base, head out on a bike trip around the island, visit the world-famous Whaling Museum, park your umbrella on a beautiful beach or embark on a whale-watch or harbor cruise. Accommodations at our AAA Four-Diamond resort range from spacious one-to-four bedroom suites with kitchenettes and spacious living areas (some with private decks), to private cottages.
Junior Suite - Inn at Hastings Park - Lexington, MA
Inn at Hastings Park

2027 Massachusetts Avenue Lexington, MA, 02421 Phone: 781-301-6660

History is at your doorstep when your family stays at this luxury inn

Inn at Hastings Park will be tentatively reopening in September 2020. Please visit our website for updates.
Just 15 miles from Boston, The Inn at Heritage Park, steps away from the battle green where the War for Independence began and other historic sites, boasts that its hospitality is truly revolutionary. See for yourself when you and your family check into a spacious and elegant room or suite. Or ask about the Pint-Sized Patriots Package, where the kids get tricorne hats, slippers and robes (plus milk and cookies!). Whether you’re riding complimentary bikes on the much-loved rail trail, hiking around Walden Pond, picking apples at an orchard or touring Louisa May Alcott’s home, you will love your Lexington area experience – and the modern amenities and comforts of this historic and multiple award-winning inn.
Starlight Lodge - family Friendly - Pool
Starlight Lodge Cape Cod

203 Main Street Route 6A (Old King's Hwy.) Dennis, MA, 02638 Phone: 508-385-3464

From this centrally located inn, families can truly enjoy all Cape has to offer

Families love the Cape, and it’s no wonder, with all it offers. At the Starlight Lodge Cape Cod, in the seaside town of Dennis, families have space to stretch out in one of 26 rooms or two suites, all with refrigerators or kitchenettes. Relax in the pool or by the fire pit or picnic area or visit nearly beaches, some only a mile or two away, the Cape Cod National Seashore, the rail trail or hiking trails. Take in an art museum, cinema or theater. Hike up to Scargo Tower to see the lake shaped like a fish. Or head into Provincetown or Hyannis for shopping and whale-watching. Up to two children under 12 stay free when using existing beds.
View from the Balcony - Green Harbor Waterfront Lodging - East Falmouth, MA
Green Harbor Waterfront Lodging

134 Acapesket Road East Falmouth, MA, 02536 Phone: 508-548-4747 Toll-Free: 800-548-5556

Unending list of things to do for you and your family with this resort as your HQ

With Green Harbor Waterfront Lodging as your headquarters, you and your family will love exploring Cape Cod, from the nearby Shining Sea Bike Path and picture-perfect beaches to great fishing, dining and shopping. At the resort, take advantage of the heated outdoor pool and the acres of open space for croquet, badminton and horseshoes. Take a rowboat or paddleboat out onto the quiet inlet or build a sandcastle on the beach. Quick trips take you to Martha’s Vineyard ferries, a scenic railroad, arcades, tennis courts, golf courses, concerts, baseball games and museums. Accommodations include waterview balconies and patios and kitchens for light cooking (or use one of the resort barbecue grills). Is Fido part of the family? Green Harbor is pet-friendly!
The Cottages at Nantucket Boat Basin - Unique Waterside Lodging - Click here to book now!
Your Vacation, Your Choice - 13 Cape and Island Resorts! Call 866-MYVACATION or click to visit our website today!
Kids - Old Sturbridge Inn & Reeder Cottages - Sturbridge, MA
Old Sturbridge Inn & Reeder Family Lodges

369 Main Street Sturbridge, MA, 01566 Phone: 774-304-1011

The family place to stay at Old Sturbridge Village

A perfect family destination and lodging combination. Explore the living history at Old Sturbridge Village then stay in your choice of two bountiful lodgings adjacent to the Museum. The Reeder Family Lodges offers 29 modern units with free continental breakfast. Stay at the historic 10-room Oliver Wight House and you’ll find four-poster canopy beds, embroidered bathrobes and slippers and adjoining room options for large parties. Signature Touch spa services are also available at the cottages. All guests enjoy the swimming pool, the kid’s playground, and the collection of 19th-century toy and game baskets. Discounted admission to OSV is included with every reservation and special packages and discounts are available for OSV members and Discovery Adventure participants during vacation weeks.
Indoor Pool 500x250 - Doubletree Boston North Shore - Danvers, MA
DoubleTree by Hilton Boston North Shore

50 Ferncroft Road Danvers, MA, 01923 Phone: 978-777-2500

A Splashtastic Fun Family Getaway!

Stay & Play just 19 miles north of Boston. Book an Overnight Package including family-friendly accommodations and access to our on-site CoCo Key Water Park. Our 65,000 square foot indoor water park is a kaleidoscope of awesomeness that is sure to delight every member of your family. Your kids will love the thrills of our giant water slides, while adults can relax in our tropical themed retreat. Conveniently located at the intersection of I-95 and Rt. 1, with ample free parking. On-site restaurants. Pet-friendly.
Outdoor Pool View - ShoreWay Acres Inn - Falmouth, MA
ShoreWay Acres Inn

Historic Shore Street Falmouth, MA, 02541 Phone: 508-540-3000 Toll-Free: 800-352-7100

Family-managed inn welcomes visiting families to enjoy all Cape has to offer

ShoreWay Acres Inn, an unique alternative to generic motels, prides itself on being family owned and operated, one reason families have been coming to this historic property for years, to relax in its indoor and outdoor pools, to let the kids play badminton on the lawn, dive into the “no-tech” toy chest or swing in the swings, to chow down on clambakes (or that complimentary hot breakfast) or tell stories and eat s’mores by the fire pits. Ask for rooms with a kitchen, or one opening onto an outside patio or balcony or, for more room, a studio or cottage-style accommodation. Nearby activities include a bike trail, Martha’s Vineyard ferry and a village stocked with fun stores and restaurants.
New Lobby - Hampton Inn Boston-Natick - Natick, MA
Hampton Inn Boston-Natick

319 Speen Street Natick, MA, 01760 Phone: 508-653-5000

Boston-area hotel makes it easy, and affordable, to enjoy fun family time

Feeling like the time is right for a family vacation? Looking for a place that offers value, consistency – and fun? Take a look at what the Hampton Inn Boston-Natick has to offer. Reserve a studio suite and you and the kids can really stretch out, enjoying free wifi and comfy beds. (Go to the hotel website for details on the industry-leading CleanStay program.) After your free hot breakfast, and perhaps some time in the 24-hour fitness center, you can do some shopping at the nearby Natick Mall (which includes Newbury Comics, Aeropostale and Hollister) or head to the three-lake Cochituate State Park for windsurfing, fishing or just a relaxing family barbecue. And, Boston is a 25-minute drive away.
Kids on Beach - Winnetu Oceanside Resort - Edgartown, MA
Winnetu Oceanside Resort

At South Beach on Martha's Vineyard -- 31 Dunes Road Edgartown, MA, 02539 Phone: 508-310-1733 Toll-Free: 866-335-1133

Special kids’ activities, family-friendly accommodations at this beachside resort

Winnetu is open for the 2020 season! New this summer. Private experiences, private dining, and fun family activities - click here for more info.

Got kids? The Winnetu Oceanside Resort has you covered for a fun-filled family vacation. With two heated outdoor swimming pools, antique fire truck rides, a water taxi ride to bustling Edgartown and a 250-yard walk to beautiful South Beach, the resort has something to keep everyone entertained. Special programs for parents and toddlers as well as day and night programs for children round out the activities. Teens will love the life-size chess set, tennis and a lawn perfect for Frisbee, soccer and whiffleball. Dining at The Dunes restaurant is a breeze, with a special Kids’ Corner area for families. Comfy accommodations range from hotel suites with kitchenettes to garden cottages and private homes perfect for multi-family vacations.
Cozy Cabin Style - Seawinds II - Dennisport, MA
Seawinds II

128 Old Wharf Road Dennisport, RI, 02639 Phone: 508-398-1474 Toll-Free: 866-469-8222

Resort asks: Is there a better place for vacationing families than Cape Cod?

Cape Cod has been entertaining families for decades, and you can join in the fun when you book a fully furnished condo unit at Seawinds II in Dennisport. You can walk from your one- or two-bedroom unit (with gas fireplace and kitchen) to a private sandy beach, hit the pool at a nearby sister resort – or go exploring! Catch a wave at one of the National Seashore’s oceanside beaches, do some funky shopping in Hyannis, catch a whale-watch boat out of Provincetown, go biking on the Cape Cod Rail Trail, visit a nature sanctuary or museum or lighthouse. See some local theater, check out a concert and dine on the freshest seafood the coast has to offer.
Playground - Beachside Village Resort - Falmouth, MA
Beachside Village

45 Surf Drive Falmouth, MA, 02540 Phone: 508-548-3975 Toll-Free: 866-469-8222

Cape Cod means unending list of activities for families, starting at this resort

There is so much to do on Cape Cod, and at the Beachside Village Resort, that starts right on the property with an outdoor heated pool, a children’s playground, picnic tables and grills. The soft sandy beach is right across the street, and the rooms, with kitchenettes, wifi and outdoor seating, are big enough to allow families to really get comfortable. Bike trails are less than half a mile away, and the village, less than a mile away, has all sorts of family attractions, from baseball games and outdoor concerts to great seafood places, interesting museums and fun shops. As for the rest of the Cape, from breathtaking beaches to arcades, mini golf, whale-watching and boat excursions, there is something for everyone to love.
Indoor Pool New 2019 - Cape Winds Resort - Hyannis, MA
Cape Winds Resorts

657 West Main Street Hyannis, MA, 02601 Phone: 508-778-4949 Toll-Free: 866-469-8222

Everyone’s a kid on Cape Cod!

Bring the family to Cape Winds and find great comfort and value and in a Cape Cod vacation. One and two bedroom units all with patio or deck have king or queen-size beds, living and dining areas, fully equipped kitchens, 1.5 -2 baths and complimentary Wifi. A fitness center and clubhouse with fireplace frame the heated indoor pool and whirlpool spa. A picnic area comes with volleyball, horseshoes and shuffleboard. Swim and tan on nearby Craigsville Beach or relax on one of America’s Top Ten beaches in nearby Nauset. Great food, shopping, entertainment and history make Hyannis a gathering place for families visiting the Cape. Sail out of Hyannis harbor on a fishing trip or take off on a day cruise to Martha's Vineyard or Nantucket. It’s all good!
Jiminy Peak Mountain Resort Family Activities Hancock MA
Jiminy Peak Mountain Resort

37 Corey Road -- Route 43 Hancock, MA, 01237 Phone: 413-738-5500 Toll-Free: 800-882-8859

Your family belongs here

Jiminy Peak Mountain Resort offers lodging perfect for any Berkshire getaway. Choose from Country Inn Suites,or two or three bedroom mountainside Vacation Homes. Amenities and activities include shopping and dining in the Village Center and Country Inn, outdoor heated swimming pool, the In-Touch Day Spa, fitness room, game room and more. Jiminy Peak is also home to the largest ski and snowboard resort in southern New England. Jiminy's 45 trails and 9 lifts cater to all skill levels and fun for all, while our three terrain parks provide rails and jibs for the new and experienced park riders.
Since opening in 1948 Jiminy Peak has evolved to become a 4 season resort, our mission to provide memorable, Mountain Resort experiences with outstanding service in beautiful surroundings.
Indoor Pool - Best Western Cape Cod - Hyannis, MA
Best Western Cape Cod Hotel

1470 Iyannough Road Hyannis, MA, 02601 Phone: 508-771-4804

Affordability, comfort and convenience on Cape Cod

Cape Cod, families and their pets are a natural at this vacation headquarters with historic charm and modern amenities. Comfortable rooms feature two double beds, hairdryers, irons and boards, 25" TVs with free HBO, pay-per-play Nintendo, pay-per-view movies, and coffeemakers. Some King Bed rooms have sofas, coffee tables, microwave and refrigerator while the spacious guest suite offers a relaxation room that is ideal for families. Start your day’s adventures with a healthy morning buffet. Enjoy the indoor heated pool, sauna, fitness center, and private sun deck. You’re just five miles from the restaurants, quaint shops and historic landmarks of downtown Hyannis where you will enjoy free long-term parking as a guest of the hotel. Check out the year-round lodging deals.
Rockport Inn and Suites Exterior Rockport MA
Rockport Inn and Suites

183 Main Street Rockport, MA, 01966 Phone: 978-546-3300

With this inn as a home base, families can set out on North Shore adventures

Think of the Rockport Inn & Suites as a great headquarters for your family to set out on its exploration of the beautiful North Shore. The hotel, on five acres in picture-perfect Rockport, is a quiet, comfortable place to relax in a spacious room or suite, with handy refrigerators and microwaves; to chill out in the indoor pool or hot tub; or to work out in the fitness center. Fueled with the complimentary continental breakfast, you and the kids can take a short walk downtown for shopping, galleries, beaches and restaurants or a short drive to a variety of attractions, from state parks to performance centers. Go kayaking, make like a pirate on a pirate-ship cruise, go whale-watching, check out museums – or grab the train into Boston!
Outdoor Pool - Holly Tree Resort - West Yarmouth, MA
Holly Tree Resort

412 Main Street -- Route 28 West Yarmouth, MA, 02673 Phone: 866-469-8222

Mid Cape family fun on and off site

Located in the heart of historic Cape Cod, this family oriented fun-filled vacation destination features studios, one bedroom suites, private entrance townhouse studios and suites, and deluxe suites with in-room whirlpools. Each unit is equipped with a refrigerator, coffeemaker, toaster, microwave and tableware. Relax in the indoor or outdoor pools while the kids enjoy their own wading pool. Guest facilities include an arcade, health center, racquetball court, basketball courts, cook-out/picnic facilities, and seasonal activity programs for both kids and adults. Conveniently located in the Mid-Cape area, you’re minutes from Cape Cod's beautiful beaches and harbors and the quaint villages of Provincetown, Hyannis, Falmouth and Chatham with great dining, theatres, nightlife, and family attractions.
Fall at Whitney's Farm Market in Cheshire - The Berkshires of Western MA - Photo Credit Ogden Gigli
The Berkshires of Western MA

The Berkshires has a full range of family friendly lodgings

Not only does the Berkshires of Western MA have your family fun covered, they’ve got a mix of lodging options to fit your family’s needs and budgets. Be it a bed and breakfast, local resort, rental property or hotel, you can find one to accommodate your family from the rolling hills of Williamstown to the quaint streets of Great Barrington and anywhere in between. So pack up the entire family and get out & about in the Berkshires. Whether you choose to spend your time indoors or out, the Berkshire region is a welcome respite in the summer. To learn more visit us at berkshires.org or find us on Facebook at Visit the Berkshires of Western Massachusetts.
Double Guest Room 500x250 - Doubletree Boston Bedford Glen - Bedford, MA
DoubleTree by Hilton Boston-Bedford Glen

44 Middlesex Turnpike Bedford, MA, 01730 Phone: 781-275-5500

We invite you to join us and see for yourself!

A great family vacation location! On-site, delight in outdoor activities include volleyball, horseshoes, bocce ball and basketball. Recreational activities include an indoor pool, exercise room, sauna, and two indoor/two outdoor tennis courts. Doubletree by Hilton Bedford Glen is also near historical and recreational sites, including Lexington & Concord, golf courses and Wachusett Mountain and Nashoba Valley ski areas. The Hotel is only 20 miles from the downtown Boston area and Logan Airport. There is easy access to local corporate offices, top shopping, Boston area universities and colleges, and New Hampshire. All 281 guest rooms and suites offer views of the meticulously groomed grounds and garden. This retreat property is located on 24 wooded acres. Come enjoy dinner on our outdoor terrace.
Indoor Pool New 2019 - Courtyard Resort - Hyannis, MA
Courtyard Resort

125 North Street Hyannis, MA, 02601 Phone: 508-775-8600

Hunker down in Hyannis or head out to the rest of the Cape from this resort

The kids might never want to leave Hyannis. There is so much to do in this lively Cape village, and you are in the center of it all at the Courtyard Resort. You can walk to mini golf courses, candy shops, a carousel, the John F. Kennedy Museum, an arcade, fun shops, great restaurants, harbor cruises – and the ferries to Martha’s Vineyard and Nantucket. Or maybe you’ll just want to stay in, enjoying your comfortable condo unit with refrigerator, microwave and cooktop as well as the resort with its indoor pool, sauna, firepits in the outdoor courtyard and barbecue area. You’re a short drive to dozens of beaches, movies at the Cape Cod Mall, live entertainment venues – even a tour at the Cape Cod Potato Chip factory!
Pottery Lesson Kids - Deerfield Inn - Deerfield, MA
Deerfield Inn

81 Old Main Street Deerfield, MA, 01342 Phone: 413-774-5587

Explore family-friendly attractions from this inn in historic Deerfield

Your family-friendly day at the Deerfield Inn begins with a hot country breakfast, followed by a day of explorations, perhaps starting with the town itself with child-friendly museums including Historic Deerfield and the Memorial Hall Museum with 19 exhibition rooms featuring everything from the world’s largest pumpkin pie pan to tombstones and Native American artifacts. Nearby attractions include a butterfly garden, a winter sports area, the Basketball Hall of Fame, Mystic Aquarium, outlet shopping and Yankee Candle’s flagship store. Visit the animals at the Hancock Shaker Village or check out a whaling ship at Mystic Seaport. Then come back to a comfort-food dinner at the inn’s restaurant and tavern. Some inn rooms offer sleep sofas or can accommodate roll-away beds.
Publick House Historic Inn On the Common Exterior Sturbridge MA
Publick House Historic Inn On the Common

277 Main Street - Route 131 Sturbridge, MA, 01566 Phone: 508-347-3313 Toll-Free: 800-782-5425

Families will feel the home-away-from-home atmosphere at this picturesque inn

Families will feel right at home at the Publick House, and that’s the way the hospitable staff wants it. Stay in the Chamberlain House (one of four lodging facilities), with suites perfect for spending a weekend with all present, or in the Country Lodge (especially if your family includes pets!). Some rooms at the inn have refrigerators, and all are equipped with modern amenities and a sense of real comfort. That’s key, too, to meals at the inn, whether they’re on the patio or inside in a tavern or great room with cathedral ceilings. The cuisine is really down-home, from turkey dinners to clam chowder. Desserts at the famous Bake Shoppe are beyond delicious. Kids will want to visit nearby Old Sturbridge Village. (Check the website for updated health and safety regulations.)
Jacuzzi & Indoor Pool - Sea Mist Resort - Mashpee, MA
Sea Mist Resort

141 Great Neck Road South Mashpee, MA, 02649 Phone: 508-477-0549 Toll-Free: 866-469-8222

Mashpee’s "Family Friendly" Resort

Set on 20 quiet, wooded acres just five miles from Nantucket Sound between Falmouth and Hyannis. It’s Cape Cod’s bucolic south coast where beautiful beaches, shopping, on the water adventures, and delicious local seafood are all within shouting distance. It’s 90 comfortably appointed one and two bedroom condos with a stocked, full-sized kitchen, queen beds, two full bathrooms, and all your linens and paper goods. This is a kid’s paradise with mini-golf, volleyball, horseshoes and shuffleboard. Unwind in one of the large pools or hot tub or get some time at the exercise room or the two tennis courts. Local marinas can set you up with equipment rentals, fishing charters, and excursions to Martha’s Vineyard and Nantucket.
Double Room - Taj Boston Hotel - Boston, MA
The Newbury Boston

1 Newbury Street Boston, MA, 02116 Phone: 617-536-5700

The Crown Jewel of Boston Hotels

Enjoy your own magic carpet ride at Boston’s distinctive 1927 landmark hotel. The Newbury is a great family destination for a weekend getaway with 273 guestrooms and 44 spacious suites featuring classic touches and windows that open to panoramic views of Boston. The Hotel overlooks the Public Garden with its swan boats and Frog Pond for ice skating while within walking distance, you’re in the heart of great eating and shopping, historic sites and attractions, galleries, movie theaters and the Hynes Convention Center. The same great Newbury hospitality, service and amenities are available for you and your family while the Hotel also welcomes pets year-round – up to two per room – and provides each pet with their own pet bed and food & water bowl.
Indoor Pool - Massachusetts Timeshares - Various Locations
Massachusetts Timeshares

Family-friendly accommodations all across Massachusetts

If you're looking for family-friendly accommodations in Massachusetts, timeshare resorts are the perfect solution. The spacious, well-appointed units offered at these properties allow you and your family to enjoy a comfortable and relaxed stay. Timeshares are great for the budget-conscious, as you can rent one for less than the cost of an average hotel and they come equipped with many more features such as full kitchens and multiple bedrooms. VacationOwnership offers timeshare rentals in Massachusetts at popular resorts including Vacation Village in the Berkshires, and Silverleaf's Oak N' Spruce. These resorts offer sought-after amenities such as indoor pools, hot tubs, and more. VacationOwnership also offers timeshares for sale in Massachusetts allowing your family to secure a lifetime of affordable vacations. Call 866-633-1030 or visit our website by following our link above for more information.
Indoor Pools - Brewster Green - Brewster, MA
Brewster Green

203 Lund Farm Way Brewster, MA, 02631 Phone: 508-896-7551 Toll-Free: 866-469-8222

History, family fun and the sea!

Brewster Green welcomes you to taste the local flavors – history, sea and sky, great seafood, shopping and whatever whets the family appetite. Amenities include an exercise room, indoor and outdoor pools, tennis and racquetball courts, shuffleboard and volleyball. Two and three bedroom condominiums include full kitchen, dining room, living room with fireplace, flat screen TV and washer and dryer. For history, visit Plimoth and Heritage Plantations, the Pilgrim Monument. For exercise and amusements, try our quaint seaside and bayside villages with museums, an Audubon center, bowling, biking and hiking trails, movies, and a chance to have a personal encounter on a whale watch excursion. And the beaches – always and a lot of them - along Cape Cod National Seashore. Inspiring families for centuries.
Pool View 500x250 - The Cove on the Waterfront - Orleans, MA
The Cove on the Waterfront

13 South Orleans Road - Route 28 Orleans, MA, 02653 Phone: 508-255-1203 Toll-Free: 800-343-2233

Make the most of your family’s seaside vacation at this comfy waterfront inn

Your family vacation by the sea should start at The Cove, a welcoming waterfront motel in the heart of Orleans. Ideal for families with its sparkling pool, picnic tables and grilling areas, fire pit, outdoor shuffleboard and cornhole games and a waterfront dock for launching paddleboards, kayaks and canoes, the comfortable year-round inn is also in the perfect place to explore all the Cape offers, from fun restaurants and shopping to biking or romping in the surf of the breathtaking Cape Cod National Seashore. Tool down to Provincetown for whale-watching, admire the views as you hike a winding nature trail, explore a lighthouse or just sit back in your waterview room and watch the sun set over the bay.
Pond and Kids Pleasant Bay Village Resort Chatham Massachusetts
Pleasant Bay Village Resort

1191 Orleans Road Chatham, MA, 02633 Phone: 508-945-6061

Cape Cod resort provides fun, activities for kids of all ages

Children and adults alike will find much to love at Pleasant Bay Village, set on six acres in the picturesque town of Chatham. Check in to your two-bedroom suite or deluxe efficiency with modern kitchens or kitchenettes, many with private sundecks or patios with Weber grills. Take advantage of the resort’s delicious breakfast, maybe have lunch by the sparkling outdoor pool. (And don’t forget cookies in the lobby.) There’s a playground set in the gorgeous gardens, pingpong and shuffleboard, but you might want to take the kids out to nearby beaches or to go on a whale watch, bike on the Cape Cod Rail Trail, go to a Cape League baseball game or enjoy a community band concert. Chatham is filled with fun shops and great restaurants the whole family will enjoy.
Indoor Pool - Cape Cod Holiday Estates - Mashpee, MA
Cape Cod Holiday Estates

97 Four Seasons Drive Mashpee, MA, 02649 Phone: 508-477-3377 Toll-Free: 866-469-8222

Spacious and Cape Cod friendly for the whole family

Located on the southern coast of Cape Cod, just a short distance from Nantucket Sound and South Cape Beach, this family friendly vacation resort offers 1, 2, and 3 bedroom units on a one-third acre lot with a spacious sun deck or patio. Each unit includes a full kitchen, wireless Internet access, central air, a washer/dryer combo (except our one-bedroom units), charcoal grill, cable TV, DVD player, and Jacuzzi tub (except in 1-bedroom units). More great resort amenities include an indoor pool, BBQ/picnic area, children’s play area, tennis, basketball, playground, game room, shuffleboard, putting green, and laundry facility. This enchanting setting is just a short trip to excellent boating, fishing and whale watching excursions. The warmth and fun of a New England family adventure is here.
Indoor Pool - Salem Waterfront Hotel - Salem, MA
Salem Waterfront Hotel

225 Derby Street Salem, MA, 01970 Phone: 978-740-8788 Toll-Free: 888-337-2536

Stay at this waterfront hotel and join the list of families who flock to Salem

Families have fallen in love with Salem for decades, and now you can, too, starting with your stay at the Salem Waterfront Hotel & Suites. From your junior or king suite, make plans to visit the Salem Witch Museum, the New England Pirate Museum, take a trolley tour of the old town or go for a harbor cruise or whale watch. Or just stroll through the shops of Pickering Wharf. With the hotel’s Family Vacation Package, there are discounts from the wharf’s shops, plus kids under 12 eat free from the children’s menu (and get a special welcome gift). The hotel has a heated indoor pool, fitness center and pub-restaurant with a menu filled with salads, chowders, sandwiches and burgers.
Lobby and Family - Hotel on North - Pittsfield, MA
Hotel on North

297 North Street Pittsfield, MA, 01201 Phone: 413-358-4741

Hotel on North is a Hospitable Base for a Family Trip

Hotel on North in downtown Pittsfield is centrally located in the wonderful Berkshires region, a great place for a family vacation with kids. From this home base – where the family can kick back in comfort before or after the day’s excursions – you can explore the hiking, biking, swimming, and picnicking at the region’s state parks; drive up magnificent Mount Greylock; attend concerts, live theater, and dance shows; and explore fascinating historic homes and gardens of the Gilded Age. For a more-restful interlude at the hotel, unleash your children in the kids’ playroom, where they can play games, ping pong table, foosball, or tuck into books in a bean bag chair. The restaurant welcomes young ones with a kids menu. The hotel’s downtown location makes it easy to explore.
Ponds at Foxhollow Exterior Lenox MA
Ponds at Foxhollow

Route 7 Lenox, MA, 01240 Phone: 413-637-1469

Boundless activities to keep families entertained at this mountain resort

Family activities at the welcoming Ponds at Foxhollow begin at the mountain resort itself: On the 223-acre estate, sheltered by towering pines, there is plenty of room to hike, cross-country ski, take a canoe or rowboat out on the winding pond, play tennis or bocce. There are indoor and outdoor pools, games, bikes, a playground and movies to rent. One- and two-bedroom condo units are spacious, with full kitchens, dining and living areas as well as decks with pond views. Barbecue on one of the resort grills or head into one of the delightful towns to dine, shop, see a play, visit a museum, hike up a mountain, head to a beach or hear a concert.
Outdoor Grills - Harbor Landing - Vineyard Haven, MA
Harbor Landing

15 Beach Street Vineyard Haven, MA, 02568 Phone: 508-693-2600

Family time is fun (and affordable) at this Vineyard Haven resort

Relax as a family at Harbor Landing, a timeshare resort in the heart of Vineyard Haven. Rent an efficiency or something bigger, enjoy the fully equipped communal kitchen, TV in the recreation room or cookouts on the patio. Nearby activities include swimming, boating, hiking, movie-going, shopping and checking out the homes of whaling captains. The lovely town beach at Owen Park has a perfect small park for the little ones. A short jaunt takes you to wildlife sanctuaries, lighthouses, horseback riding, biking and hiking trails in state and national parks, arcades and to the famous Flying Horses Carousel at Oak Bluffs. Come back to the resort to unwind on the deck while the sun sets over the water.
Young Fisherman - The Cottages at Nantucket Boat Basin - Nantucket, MA
The Cottages at Nantucket Boat Basin

Several Wonderful Locations Nantucket, MA, 02554 Phone: 508-325-1000 Toll-Free: 800-475-2637

Beaches, bikes and a cottage to call home: the perfect family vacation

The privacy of a cottage and the fun of an island resort: It’s a perfect combination for a stress-free family vacation. At The Cottages at the Boat Basin, relax in your spacious cottage, with a full kitchen, then explore all Nantucket has to offer, from its 80 miles of beaches to whale watches and ice cream cruises to kid-friendly museums and restaurants. At the resort, grab bikes to see the sights or get a beach umbrella and plunk down in the sand (some beaches have playgrounds and concession stands). Special fun for children at the resort includes scavenger hunts and kid-sized fishing kits. A pre-arrival concierge will help you plan your perfect family vacation.
Indoor Pool 500x250 - Baymont Inn & Suites - Plymouth, MA1
Baymont Inn & Suites Kingston Plymouth Bay

149 Main Street Kingston, MA, 02364 Phone: 781-585-3831

Affordable family lodgings near historic attractions

Bring the family to see, hear and experience one of America’s most historic first colonies where in 1620 William Bradford and Pilgrims stepped off the Mayflower. This family friendly hotel is close to Plymouth Rock, the Mayflower II, Plimoth Plantation and the Pilgrim Hall Museum. The 100% non smoking hotel offers all your amenities at a great price from free WiFi and free Baymont Breakfast Corner, a 24-hour fitness center and a micro-mart for everyday essentials. You’ll find a microwave and mini-refrigerator, flat-screen HDTV, ironing facilities, and a tea and coffee maker. Children under 17 stay free and bring your pet for a one-time $25.00 charge. Be sure to check out Duxbury Beach Park, Plymouth Bay Winery, and Brewster Gardens.
Kickball on the Lawn 500x250 - Briarclif Motel - Great Barrington, MA
Briarcliff Motel

Route 7 - 306 Stockbridge Road Great Barrington, MA, 01230 Phone: 413-528-3000

From this fun, affordable motel, launch your family’s Berkshires adventure

The folks at Briarcliff, a re-imagined classic 1960s motel on scenic Route 7 between Stockbridge and Great Barrington, like to say that their comfy, stylish rooms are Instagram-worthy, which will appeal to the kids. But so will everything about your stay in the bed and breakfast, from the homemade granola and muffins in the morning to making new friends around the firepit at night. And there is so much to do in between, from skiing at nearby Butternut to hiking Monument Mountain (the trail is right across from the Briarcliff) to touring the Norman Rockwell Museum or MassMOCA to sitting on the lawn for a Tanglewood concert. Everything it just minutes away, and your hosts will be happy to help you plan a fun family itinerary.
Family Friendly - Oak & Spruce Resort - A Holiday Inn Club Vacations Getaway - Lee, MA
Holiday Inn Club Vacations Oak & Spruce Resort

190 Meadow Street South Lee, MA, 01260 Phone: Toll-Free: 866-454-5101

More room for the whole family

Guests can discover fun-filled amenities and spacious villas in the heart of the Berkshire Mountains at Holiday Inn Club Vacations® Oak n’ Spruce Resort. The resort features one-, two- and three-bedroom villas with fully equipped kitchens, a private balcony/patio as well as complimentary Wi-Fi and parking. The resort also offers a host of activities that the whole family will enjoy including indoor and outdoor pools, a miniature golf course, movie theater, playground, fitness center and an activity center. Additionally, guests can experience fresh, outdoor air with nearby hiking or biking along the beautiful paths of the Appalachian Trail or visiting the neighboring ski areas for fun in the winter months.
Outdoor Rooftop Dining 500x250 - Battery Wharf Boston Hotel - Boston, MA
Battery Wharf Boston Hotel

Three Battery Wharf Boston, MA, 02109 Phone: 617-994-9000 Toll-Free: 800-257-7544

So much for families to do, and this harbor hotel is in the perfect spot for your HQ

It’s hard to imagine a more convenient and comfortable spot for enjoying all Boston that offers families than the Battery Wharf Hotel. The hotel is steps from the lively North End, steeped in fun dining and history; the eclectic shops and eateries of Fanueil Hall; and the amazing New England Aquarium. Walk out the door to stroll along the pedestrian-friendly Harbor Walk or the historic sites of the famous Freedom Trail. Watch the boats come into the harbor from your spacious room or suite, complete with a state-of-the-art entertainment system. Ask about the Family Fun Package, which includes two connecting rooms and an exclusive North End scavenger hunt.
Family Fun 500x250 - Cape Codder Resort & Spa - Hyannis, MA
Cape Codder Resort & Spa

1225 Iyannough Road Hyannis, MA, 02601 Phone: 855-861-4370

Spend quality time with your family at the Cape Codder Resort and Spa....you may never want to leave!

Make a splash in the NEW Water Park with huge water slides, lazy river, wave pool, retractable roof and so much more or in the Rainbow Falls Heated Outdoor Pool, pamper yourself (kids too) in the full-service Beach Plum Spa, roast marshmallows by our bonfire, take in dinner under the stars or enjoy live entertainment on The Deck, lounge or play in our beach-like area, savor breakfast, lunch or dinner in our Hearth ‘n Kettle Restaurant and Tavern, enjoy bistro-fare, award-winning wines and live jazz in our Grand Cru Restaurant, watch a movie by moonlight, play games with the kids and our recreation staff and SO much more! Relax in one of our 257 guest rooms or luxury fireplace suites with oversized whirlpools. Reserve online for the lowest rate…guaranteed.
Family Bike Ride - Ocean Edge Resort & Golf Club - Brewster, MA
Ocean Edge Resort & Golf Club

2907 Main Street (Route 6A) Brewster, MA, 02631 Phone: 508-896-9000 Toll-Free: 800-343-6074

Brewster resort wants you to have the quintessential Cape Cod vacation

Your family wants a fun, relaxing Cape Cod vacation? The Ocean Edge Resort & Golf Club wants that, too! Plan your day from the comfort of your room or villa, with a kitchenette, private patio or balcony and washer and dryer. Walk to a sparkling pool, head out on the scenic bike trail, play tennis on one of eight courts or pickleball on six new courts. Arrange for an oyster-bed tour. Or just relax on the private bay beach. Snack poolside at the “Shark Bah” or dine in the pub. With the Cape’s 15 towns an hour or less away, entertainment is endless, from whale watches and seal excursions to museums and shopping. Check the website for updates on local health and safety rules.