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Lake Morey Resort - Fairlee, Vermont

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.
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

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.
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

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.
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.
Lobby and Family - Hotel on North - Pittsfield, MA
Hotel on North

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

Launch your full-scale exploration of the Berkshires from this centrally located hotel

Stay at a hotel in the center of it all when you bring your family to vacation in the Berkshires. From the 45-room Hotel on North, you can plan your exploration of this lively area, from cross-country and downhill skiing to state parks with ample opportunities for hiking, biking, swimming and picnicking. Visit art and history museums or the working farm at the Hancock Shaker Village; ride the classic wooden Berkshire Carousel; go bowling or play mini golf; or take in a concert at Tanglewood or local theater at one of several locations. The hotel has an on-site casual-dining restaurant, free parking in the back and spacious rooms, including extended-stay accommodations with a kitchenette and washer/dryer. A limited number of rooms are pet-friendly.
Your Vacation, Your Choice - 13 Cape and Island Resorts! Call 866-MYVACATION or click to visit our website today!
Mountain View Grand Resort & Spa - Casual Elegance, Stunning Views. Seasonal Promotions Available now!
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

So much for families to do, and so many lodging amenities, at spacious resort

What’s not to like at the luxurious Ocean Edge Resort & Golf Club, if you are on a family vacation? Book spacious accommodations in the sprawling, family-oriented Villages, where your villa will include a kitchenette dining room, private patio or balcony and washer/dryer. You’re just steps away from several dining options, tennis courts and golf. Kids will love trying out the resort’s five pools (ask about dive-in movie nights) or showing the adults how to play pickle ball. There’s a private beach (for Mansion-side guests; Villages guests have access to beach shuttle to nearby beach), and you can rent a new kayak or stand-up paddle board and coast through calm Blueberry Pond. Or, rent a bike and hop on the nearby Cape Cod Rail Trail. It’s a short drive to the magnificent Cape Cod National Seashore’s ocean beaches.
Kids and Flowers - Jiminy Peak Mountain Resort - Hancock, MA
Jiminy Peak Mountain Resort

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

After a day on and off the slopes at this mountain resort, it’s just a short walk to your suite or condo

The best part for families about staying at the Jiminy Peak Mountain Resort? After a fun and full day of skiing, or zip lining, or mountain biking, or snowboarding, or zooming down the mountain on an alpine slide, it’s just a short walk to your comfortable suite or vacation home. And then, after a little relaxing, it’s just a short walk to an on-site pub, tavern or shop. The Berkshire resort’s Country Inn has over 100 suites as well as an outdoor heated pool, indoor and outdoor heated whirlpools and an exercise room. Condo communities on the resort property feature spacious, well-appointed two- and three-bedroom units with full kitchens, some with washer/dryers. Check the website for lodging deals.
Cozy Cabin Style - Seawinds II - Dennisport, MA
Seawinds II

128 Old Wharf Road Dennisport, MA, 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.
Pottery Lesson Kids - Deerfield Inn - Deerfield, MA
Deerfield Inn

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

Good times await your family at this historic, welcoming Happy Valley inn

How could your family not have fun staying at a cozy historic inn in an area known as Happy Valley? The Deerfield Inn is comfortable and welcoming, with 24 spacious rooms and a suite; an inviting restaurant serving breakfast, lunch and dinner; and a parlor with board games, puzzles and a fireplace. Stroll down historic Old Main Street, visit the Flynt Center of Early American Life, check out the oldest rag doll in America in the Memorial Hall Museum or drive to see the animals at the Hancock Shaker Village or the lovely inhabitants of the Magic Wings Butterfly Conservatory and Gardens. There’s skiing and snowboarding, hiking, biking, and museums celebrating the work of Norman Rockwell and Eric Carle.
Family at Breakfast Buffet - Seaport Hotel Boston - Boston, MA
Seaport Hotel Boston

One Seaport Lane Boston, MA, 02210 Phone: 617-385-4000

Walkable, bike-able Boston and the comfortable Seaport Hotel is a great family-centric combo

Walkable, historic Boston is a great place for family vacations, and there’s no better launching pad than the Seaport Hotel, perfectly situated in the heart of the exciting Seaport District. The hotel’s spacious rooms and suites, with super harbor and city views, mean lots of room to stretch out and plan your busy days, from hiking the Freedom Trail to visiting the nearby Boston Children’s Museum and Tea Party Ships & Museum. Explore this vibrant neighborhood on one of the hotel’s complimentary bikes. Come back for dinner on the open-air terrace at TAMO Bistro + Bar. Ask about the First Mate’s Club, providing a year-round scavenger hunt and amenities for kids, starting with a toy they can select from Seaport’s Treasure Chest upon arrival.
Winter Family Outing - The Berkshires of Western MA - Photo Credit Ogden Gigli
Visit the Berkshires of Western Massachusetts

A Cozy Stay for the Whole Family in the Berkshires

Relax and unwind in true Berkshire style this winter season with a frosty getaway to the Berkshires of Western Massachusetts. Our one-of-a-kind inns, hotels, and resorts offer unique experiences for every budget and taste, from kid and pet-friendly casual digs to upscale, splurge-worthy escapes. Explore some of the area’s favorite lodging experiences to book the perfect stay - serene winter landscapes, myriad museums, farm fresh dining, eclectic shopping, and so much more await! To learn more click our listing link or search “Visit the Berkshires of Western Massachusetts” on Facebook.
Indoor Pools - Brewster Green - Brewster, MA
Brewster Green Resort

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

It’s a vacation wrapped in a vacation when you stay at this amenity-filled Cape resort

It’s almost like a vacation inside a vacation when you and your family stay at the Brewster Green Resort. Just off historic and picturesque Route 6A on the Cape’s north coast, the resort is a short drive to National Seashore and bay beaches, museums, golf, charter fishing, lighthouses, ponds and lakes and all the natural wonders of Nickerson State Park, from hiking trails to access to the scenic Cape Cod Rail Trail for bikers. But the resort itself has indoor and outdoor pools, tennis and volleyball courts, nature trails, a horseshoe pit, sauna, hot tub and a children’s playground. Two- and three-bedroom units have full kitchens, fireplaces, patios or balconies with grills and a washer/dryer (plus two TVs!).
Indoor Pool - Massachusetts Timeshares - Various Locations
Massachusetts Timeshares

From the mountains to the coast, Massachusetts has timeshares for that perfect family getaway

From the breath-taking Berkshires to bustling Boston and the shimmering shores of Cape Cod, Massachusetts has exactly what you need for that memorable family vacation. And what better way to relax than by purchasing a spacious, comfortable timeshare from one of the dozens offered in Massachusetts? Walk the Freedom Trail in Boston from your timeshare in Marriott’s Custom House, ski or hike through the beautiful Berkshires when you stay at Silverleaf’s Oak ’n’ Spruce in South Lee. On the Cape, timeshare ownership opportunities from Falmouth to Provincetown mean you can visit exceptional arts venues, golf on championship courses, shop ’til you drop in seaside villages and, of course, enjoy all the beach and water activities this famous coastal vacation haven has to offer. Call 866-633-1030 or visit our website by following our link above for more information.
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

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.
Playground - Beachside Village Resort - Falmouth, MA
Beachside Village

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

Enough activities in and around this seaside resort to keep every family member happy

From tots to teens, there really is an activity to keep everyone happy when you stay at the Beachside Village, across from Falmouth’s popular Surf Drive Beach. Enjoy a day on the sandy beach, in the warm waters of the resort’s heated outdoor pool, on the nearby bike path, or take the family into Falmouth Village to catch a Cape Cod Baseball League game, take a tour of historic museums on the picturesque village green, or shop Main Street’s bookstores, boutiques and bakeries. Or drive to Woods Hole and board a ferry to Martha’s Vineyard, a mere seen miles away. Back at the resort, cook in your studio, one- or two-bedroom condo unit’s kitchenette or barbecue outside while the kids explore the playground.
Happy Kids Jumping on Bed - Greater Merrimack Valley MA
Greater Merrimack Valley

61 Market Street, Unit 1C Lowell, MA, 01852 Phone: 978-459-6150

Hotels offer roomy accommodations, dining, fitness centers while serving as your home away from home

Enjoy all the attractions and activities the Greater Merrimack Valley has to offer, from shopping to skiing, from museums to fun festivals, from your roomy headquarters at one of the area’s full-service hotels. At the Boston Marriott Burlington, come in from the cold to sip a brew by the fireplace in the newly renovated lobby or order a steak at Chopps American Bar & Grill. At Westford Regency Inn & Conference Center, take a dip in the heated indoor saltwater pool and whirlpool, part of its spacious health club. At the Sonesta Select Boston-Lowell-Chelmsford (which is pet-friendly), grab a morning cappuccino before you head out to nearby shopping. All three hotels are great places to plan your adventures in this bustling region.
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

Witches, pirates and a heated pool: Of course your kids will love this vacation!

Salem is a great place for families to explore, and the Salem Waterfront Hotel & Suites is the perfect base from which to launch your adventures. Breath-taking views, fun attractions and history are just steps away from the Pickering Wharf hotel, which has a heated indoor pool, marina, pub and patio serving three meals a day and a fitness center. Kids will love all the attractions in town that feature witches and pirates, and adults will admire the Peabody Essex Museum and the House of the Seven Gables. A heritage trail and kids tour will show you all the historical highlights. Stroll the shops on Pickering Wharf or walk out to Derby Wharf Lighthouse. Take the ferry to Boston or a coastal cruise. Ask about the Family Vacation Package.
Poolview Suite - Hotel 1620 - Plymouth, MA
Hotel 1620 at Plymouth Harbor

180 Water Street Plymouth, MA, 02360 Phone: 508-747-4900 Toll-Free: 866-719-8185

Hotel has all the ingredients – location, location, location – for a great family getaway

The ideal family vacation: a comfortable hotel, with a pool, where you can walk to all kinds of family-friendly attractions and restaurants. That’s what you get at Hotel 1620 Plymouth Harbor, right across the street from Plymouth Harbor and Cape Cod Bay. From your comfortable suite overlooking the indoor pool or the bay, you can plan your busy days in America’s Hometown. Walk down to the Mayflower II, Plymouth Rock, harbor cruises and whale watches and dozens of eateries. More restaurants and Pilgrim Hall are a couple blocks up on Court Street. Stroll along Town Brook to the Plimoth Grist Mill. There are several beaches nearby, as well as a winery, ice cream shops, galleries and boutiques. It’s a quick drive to Plimoth Patuxet Museums.
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

Something for everyone when you stay at this four-season resort in the heart of the Cape

It’s no wonder that families love vacationing on Cape Cod: There is so much to do, which means there is something for everyone. So why not stay in the heart of it all? At Cape Winds Resorts in Hyannis, you’re close to island ferries, beaches, whale-watching and harbor cruises, duck boats, great shopping, a children’s playground, arts venues and every type of dining imaginable. The four-season resort offers one- and two-bedroom units and two-level townhouse suites. Full kitchens, decks, patios and amenities including an indoor heated pool and recreation area, barbecue grills, laundry facilities, a fitness center, volleyball court, horseshoe pit and clubhouse with a fireplace make this resort a convenient, comfortable home-away-from-home for families.
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

Active, comfortable family vacations begin at this spacious historic inn

When you bring your family to the Publick House inn, you have to start your day at the Bake Shoppe for some heavenly pastries. In the summer, take a dip in the outdoor pool or enjoy the spa and fitness room. If you have young history buffs, they’ll love the Revolutionary-era ambiance, and everyone will love dining at Ebenezer’s Tavern, where light Yankee fare for lunch and dinner includes a children’s menu with a turkey meal, fish and chips and burgers. Whether you stay in a spacious room in the motor lodge or a suite in the historic inn, Chamberlain House or Tiller House (with room fridges), your accommodations will be spacious and comfortable. Nearby attractions include Old Sturbridge Village, parks and beaches.
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

Family fun begins at this friendly resort with free-standing homes for private relaxation

Why do families flock to Cape Cod? Because there is so much to do! From sailing to sunbathing, from hiking to harbor cruises, there is something for everyone on the Cape. And you can plan your fun vacation from your two- or three-bedroom home at Cape Cod Holiday Estates. Each home, with a sun deck and patio, whirlpool tub, fully equipped kitchen and charcoal grill, sits on a one-third-acre plot, surrounded by lawn and trees. You’ll have access to an indoor pool, tennis and basketball courts, a game room and children’s playground. Head off to the beach, or to stroll the Cape’s Main Streets with fun shopping and dining, take a Cape Cod Potato Chips Factory tour or visit the JFK Museum.
Bunk Beds - Franklin Hotel Martha's Vineyard - Edgartown, MA
Franklin Hotel Martha's Vineyard

222 Upper Main Street Edgartown, MA, 02539 Phone: 508-379-2100

Easy to see why families love coming to the Vineyard, and you can experience it all from this Edgartown hotel

If your family wants space to stretch out and a full slate of fun things to do, the Franklin Hotel in Edgartown has just what you all need. Its 18 unique rooms include a penthouse loft that sleeps six (with a spiral staircase to the loft) and a one-bedroom cottage off the courtyard with a kitchen and a washer/dryer. Pets under 50 pounds are welcome. It’s a short stroll into Edgartown, where the fun energy revolves around one-of-a-kind shops and restaurants. You’re close to hiking and biking trails and gorgeous beaches (think swimming, paddling, boating and fishing). You’ll want to see the historic Flying Horses Carousel in Oak Bluffs, tour lighthouses, go on the African American Heritage Trail and visit the Aquinnah Wampanoag Indian Museum.
Outdoor Pool - Holly Tree Resort - West Yarmouth, MA
Holly Tree Resort

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

Fun for families is everywhere on the Cape and at this convenient resort in the heart of it all

Fun and relaxation are right outside your door at the Holly Tree Resort. From your comfortable studio or one-bedroom suite, you have access to amenities including indoor and outdoor pools, a kids’ wading pool, a whirlpool, basketball and racquetball courts, exercise and game rooms, a playground and seasonal activity programs for children and adults. Make dinner in your kitchenette or grill in the barbecue and picnic area – or drive into one of the Cape’s many picturesque towns and villages for memorable dining (as well as shopping, gallery-hopping, museums and nightlife). You’re close to beaches, island ferries, golf courses, beautiful bike paths and hiking trails, fishing and sightseeing cruises, theaters, sporting events and historic sites. Ask about deals and last-minute resort specials.
Library Winter View - Ponds at Foxhollow - Lenox, MA
Ponds at Foxhollow

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

Four seasons of the year, families find fun activities at this exceptional mountain resort

With fun activities and great recreation four seasons of the year, the Berkshire region is a family favorite. And what better way to enjoy it than by staying in a spacious condo at The Ponds at Foxhollow. The 223-acre property is perfect for hiking, biking and cross-country skiing. There are canoes and rowboats, a playground and a putting green, indoor and outdoor pools and courts for tennis, basketball and bocce. Do a puzzle in the library or bring a movie back to your condo, with a fireplace, fully furnished kitchen and deck overlooking the pond, Head out for an adventure in the mountains, from alpine skiing in the winter to kayaking in the spring, catching a concert at Tanglewood in the summer or visiting a scenic railway museum in the fall.
Family Fun 500x250 - Cape Codder Resort & Spa - Hyannis, MA
Cape Codder Resort & Spa

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

With its water park, recreation activities and dining options, this resort is a family favorite

The Cape Codder Resort & Spa is so family friendly, you may have a hard time leaving. It starts with the water park, of course: a huge park with water slides, spouting whales, water cannons and buckets and a wave pool. It also has a whirlpool, sauna, fitness center and cafe. There are two casual-dining restaurants, an indoor arcade, a heated, year-round outdoor pool that turns into an LED light show at night, and a courtyard where you can lounge in the sand, or play basketball or pickle ball. Family suites at the resort accommodate up to six people, and special residences have full kitchens and fireplaces, for up to eight guests. Nearby activities include beaches, whale watches, cruises and ferries to the islands.

Visit our sister property - The Dan'l Webster Inn & Spa