Massachusetts is well-supplied with vacation rentals, condos, apartments

Massachusetts > State > Specialty Lodging > Vacation Rentals

Whatever you’re looking for in a vacation rental, Massachusetts has many options: year-round hotels, timeshares, townhomes, cottages, condos, studios, suites, and apartments with lots of room, privacy, comforts and unlimited recreational activity. Families, couples, and groups can pick a mountain, Oceanside, or historic setting and find a home-away-from-home getaway with every pleasure. From Stockbridge to Boston and north and south to Cape Ann and Cape Cod you’ll find one, two- and three-bedroom units some with multiple levels, spas and hot tubs, fully equipped kitchens, living and dining areas, sun decks and patios, fireplaces, televisions, and much more.

ShoreWay Acres Inn

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

A variety of longer-term vacation rentals with all the perks at this Cape inn

Looking for something longer than a weekend escape on the Cape? The ShoreWay Acres Inn, family owned and operated, has a variety of options for vacation rentals. An extended-stay-hotel part of the resort features several one-bedroom residences, and the inn complex also includes studios with kitchens, a loft studio, a one-bedroom sea captain’s house and an eight-bedroom/eight-bathroom (yes!) residence for weekly rental. Come stay at this family resort and enjoy all the perks, from firepits and indoor and outdoor pools to men’s and women’s saunas, barbecue grills and spacious grounds for all sorts of lawn games. The inn is secluded yet near everything, from charming Falmouth village to bike trails, nature sanctuaries, galleries and museums.

Yard Flagpole 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

Relax on the Cape in comfort and style!

The style and amenities in a resort and the comforts of home in your own condominium await your visit to Cape Winds. Historic Hyannis is here with great shopping and waterside eateries, fishing trips and day cruises, the Cape Cod Melody Tent and JFK Museum. One and two bedroom units all with patio or deck come with king or queen-size beds, living and dining areas, fully equipped kitchens, 1.5 -2 baths and complimentary Wifi. Some units feature two levels with a spiral staircase leading to the living and dining areas. Enjoy the fitness center and clubhouse with fireplace, heated indoor pool and whirlpool spa, picnic area, volleyball, horseshoes and shuffleboard. Whenever you arrive, Cape Winds professional staff will ensure you get the best service and value for your vacation dollar.

Beachside Village

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

Beachside resort your comfortable Cape Cod home away from home

Once a seaside mansion for a well-to-do boat captain, the Beachside Village Resort is more than the perfect launching site for your Cape Cod vacation: It’s really a home away from home. Comfortable one- and two-bedroom units, and studios, come with kitchenettes, fireplaces, patios or balconies, wifi and, in some cases, lovely ocean views with Martha’s Vineyard in the distance. You can relax by the heated outdoor pool or under an umbrella at a picnic table on the manicured lawn. The sandy beach is only a few steps away; bike trails less than half a mile; the village with shops and restaurants a mile away. Farther afield are the beaches, historic sites and waterfront attractions that have made the Cape famous.

Harbor Landing

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

Village location makes this resort a great launch site for island adventures

The charming working harbor village of Vineyard Haven is the ideal spot for a vacation getaway, and Harbor Landing, a timeshare resort, has a variety of rental units for those seeking a combination of privacy and access to the island’s many delights. Rental options range from efficiency units to double suites, and amenities include a fully equipped common kitchen, a sun deck with perfect sunset vistas and harbor views, a recreation room and a patio (great for cookouts). The resort’s central location makes it a convenient launching site for Vineyard adventures from swimming, boating, horseback riding and biking to dining and nightlife. Watch the sunset over West Chop Lighthouse, explore the village’s shops, galleries and studios.

Nantucket Island Resorts and Hotels Vacation Rentals Nantucket MA

The Cottages at Nantucket Boat Basin

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

Nantucket Is One of the world's Most Captivating Destinations.

Nantucket Island Resorts welcomes you to this unforgettable island by providing stunning locations and accommodations, unparalleled service, gracious amenities, award-winning dining and a hundred activities.
We are a collection of premier hotels and a marina on Nantucket, including The Wauwinet, White Elephant, White Elephant Village | Residences & Inn, Jared Coffin House, The Cottages & Lofts at the Boat Basin and Nantucket Boat Basin. Each offers a unique appeal for vacations, corporate retreats and weddings. We provide customized service to meet your every need.
Air and ferry service make it easy to get from Hyannis or Boston’s Logan Airport in just an hour or less. In season, you can fly from New York, Westchester, Newark, Washington, Providence and Philadelphia directly or through Boston.

Seawinds II

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

Bike, hike, tour or just plunk your chair down on the beach at this Cape resort

Vacation in comfort when you book one of the cozy condo units at Seawinds II in Dennisport, a charming village centrally located on Cape Cod. One- and two-bedroom units come with kitchens, dining tables, queen beds and queen-bed pull-out sofas, gas fireplaces and access to a nearby sister resort’s indoor and outdoor pools, whirlpool and fitness center. A private sandy beach is but steps away from Seawinds, perfect for frolicking in the bay or finally finishing that novel. The resort is a short drive to whale-watch tours, harbor cruises, galleries, museums and great shopping. Or, stroll the dramatic ocean beaches of the National Seashore, bike the scenic Cape Cod Rail Trail, catch a concert or theater performance.

Cape Cod Holiday Estates

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

The perfect setting for a home away from home Cape Cod vacation

Boasting privacy and luxury in a vacation rental, here’s comfortable and spacious units set on a one-third acre lot featuring a spacious sun deck or patio. Resort amenities include an indoor pool, BBQ/picnic area, children’s play area, tennis, basketball, playground, game room, shuffleboard, wireless internet and laundry facility. Step into your own 1,2, or 3 bedroom unit and you’ll find a full kitchen, cable TV and DVD player, living room, TV room, Jacuzzi tub (except for one bedroom units), and central air. A day out brings you to the Atlantic Ocean where you’ll be able to sail, charter a boat, or enjoy a fishing or whale watching excursion. You’re on the southern coast of Cape Cod, just a short tack from Nantucket Sound and South Cape Beach.

Cove at Yarmouth

183 Main Street West Yarmouth, MA, 02673 Phone: 508-771-3666 Toll-Free: 866-469-8222

The Cove beckons!

The Cove at Yarmouth is Cape Cod’s largest year-round resort. Affordable vacation rentals in 229 spacious suites and townhouses include living room, master bath, wet bar, refrigerator, appliances, two LCD TVs, stereo and DVD. Two pools and a fully equipped fitness facility and spa to keep you active. Washers/dryers and nearby dry cleaner and convenience store to keep you supplied and looking your best. There’s racquetball, volleyball, indoor and outdoor tennis and a children's play area. Dine by candlelight on-site and enjoy exceptional Italian Cuisine, specialty dishes and family priced meals. Located near great beaches, golf, sailing, fishing, biking and shopping in the Cape’s quaint villages. Sample the local "chowdah" and take a day tip to Martha’s Vineyard and Nantucket.

Ponds at Foxhollow

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

Vacation rentals at Berkshires resort let you truly enjoy its many amenities

Once you sample the many delights of the Ponds at Foxhollow, a 223-acre estate sheltered by towering pines in the Berkshires, you might want to come back for a longer stay. Vacation rentals at the scenic four-season resort let you continue to enjoy all its amenities, from skiing and hiking practically at your doorstep to indoor and outdoor pools; tennis, basketball, shuffleboard and bocce courts; a putting green; playground; on-site canoes for the resort’s lovely pond; and Friday wine and cheese parties in the fireplaced library. All of the resort’s one- and two-bedroom condos have Jacuzzis, full kitchens, dining and living areas and decks overlooking the pond; the two-bedroom units also have a loft sitting room.

Green Harbor Waterfront Lodging

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

Picturesque waterfront lodging offers a long menu of vacation-time activities

Capture the feeling of that great Cape vacation at Green Harbor Waterfront Lodging, where all the accommodations feature waterview balconies or patios. Chill out at the resort, in a quiet woodlands setting on a picturesque ocean inlet, with a clambake or barbecue, playing croquet or badminton, gliding down the cove on a paddleboat or swimming in the heated outdoor pool. Or, do all those things that make the Cape what it is: Go biking, hiking, gallery-hopping and shopping in nearby Falmouth village. Take a photo by Nobska Light, stroll Old Silver or Surf Drive Beach, take a scenic train ride, go antiquing, take a ferry to the Vineyard. The resort also has a private boat ramp and dock.

White Elephant

50 Easton Street Nantucket, MA, 02554 Phone: 508-228-2500 Toll-Free: 800-445-6574

Variety of rental residences from which to celebrate island life

Vacation residences at the White Elephant Hotel and nearby White Elephant Village on glorious Nantucket provide guests with the sensation of being at home and on a luxurious but laid-back vacation at the same time. Whether you choose a spacious garden cottage, a chic in-town loft or a luxury one-, two- or three-bedroom residence, you will feel like you have stepped into the pages of a beautiful-homes magazine. Each type of artfully appointed accommodation has a unique floor plan, custom furniture and island-inspired artwork. From your home away from home, you can head into town for some boutique shopping, book a harbor cruise, dine in style or relax by the pool – or by your own fireside.

Brant Point Courtyard

15 Swain Street Nantucket, MA, 02554 Phone: 508-228-0241 Toll-Free: 866-469-8222

Vacation rental with resort amenities and island comfort

Vacation rentals and time shares are yours at Brant Point Courtyard. One bedroom, one and two floor units, cottages and townhomes provide every amenity you’ll need. Fully stocked kitchen with dishwasher; living room; 1,11/2, or 2 baths; bath and bed linens; on site free laundry; gas grills; family areas; and a favorite of island visitors; an outdoor shower. Some units may also have hardwood floors, whirlpool tubs, decks, patios, and fireplaces. Perfectly positioned between Nantucket town and great beaches and private enough for peace and quiet, Brant Point Courtyard has the feel of a hotel and the comforts of a more relaxed vacation style. Shopping, dining, horseback riding, hiking and sightseeing along historic trails and at historic sites offers our visitors the very best in Nantucket charm and adventure.

Riverview Resort

37 Neptune Lane South Yarmouth, MA, 02664 Phone: 508-394-9801 Toll-Free: 866-469-8222

The perfect vacation fit for one and all

A sweet spot on Cape Cod and perfect for a family vacation, weekend escape or mid-week getaway. On the banks of Parker's River in South Yarmouth, are 44 studio, one and 2 bedroom units with all the amenities including refrigerator, microwave, coffee maker, cable TV and wireless Internet access. There’s a year-round indoor pool and fitness center, washers and dryers and a community kitchen. A game room with pool table, barbeque grills and picnic tables and an outdoor play area make it fun for any age. Centrally located and within an easy drive of Cape Cod’s 15 distinctive towns there’s shopping, great food and entertainment close at hand. You’ll also find the finest beaches and an endless array of land and sea activities along Cape Cod National Seashore.

Holly Tree Resort

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

The Cape Cod vacation rental to fit your dream

This summer, rent your vacation studio, one bedroom suite, private entrance townhouse studio or suite, or a deluxe suite with in-room whirlpools in the celebrated mid-Cape area. You’ll be minutes from beautiful beaches, historic attractions and quaint villages like Provincetown, Hyannis, and Chatham with their restaurants, theatres, nightlife, and family attractions. Each unit is equipped with a refrigerator, microwave and tableware. Included are air conditioning, TV/DVD's and Wi-Fi. Couples, friends and families will find this fun-filled summer vacation destination a haven for comfort and relaxation. There are indoor and outdoor pools, a wading pool for the kids, an arcade, racquetball and basketball courts, a health center, cook-out/picnic facilities, and seasonal activity programs.

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

Vacation in style and comfort at these beachside resort rental properties

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

Ocean breezes, a full slate of activities for every member of the family, delicious dining in a casual atmosphere, superlative service: It’s all part of the package at the Winnetu Oceanside Resort, the Vineyard’s only hotel located at the beach. If you really want to relax in style, opt for a townhouse, duplex or private home. The exclusive rentals, from two to five bedrooms, include all resort amenities, from two outdoor heated pools to day and evening children’s programs, and each home has a fully equipped kitchen; many are within an easy walk of fabulous South Beach and most have spectacular water views. Additional features include porches, outdoor decks and outdoor hot tubs. And, of course, perfect privacy.

Brewster Green

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

A condo getaway at a Cape Cod pace

Brewster Green is 17 acres of ideal vacation rental property. Amenities include an exercise room, indoor and outdoor pools, tennis and racquetball courts, shuffleboard and volleyball. 56 two and three bedroom condominiums range in size from 1,100 to 1,600 square feet, each tastefully decorated and with full kitchen, dining room, living room with fireplace, flat screen TV with VCR/DVD players and CD stereo systems, one to two bathrooms, a master bedroom with king size bed and washer and dryer. Nearby Plimoth and Heritage Plantations, the Pilgrim Monument and myriad museums add living history to your stay. There are villages seaside and bayside with great shopping and seafood, an Audubon center, biking and hiking trails, whale watching and the beach along the Cape Cod National Seashore.

Entrance Sign - Courtyard Rsort - Hyannis, MA

Courtyard Resort

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

Kick back in your comfortable condo after a busy day sightseeing on the Cape

Cape Cod beckons when you stay at the centrally located Courtyard Resort smack dab in the middle of bustling Hyannis. Vacation in style in these great condo units, with kitchen and dining areas (or maybe you want to grill outside in the courtyard). The resort includes an indoor pool, whirlpool, sauna and onsite parking. You can walk to the ferry docks and before you know it you’re on Martha’s Vineyard or Nantucket. But there’s plenty to do in Hyannis, with its museums, art galleries, boutiques, variety of restaurants, mini golf and entertainment venues. Or, drive to lively Craigville Beach or to the Lower Cape’s National Seashore and Cape Cod Rail Trail. Tour the Cape Cod Potato Chip factory or the Maritime Museum. So much to see and do!

Sea Mist Resort

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

Cape Cod’s “Stay and Play” Resort

Ninety comfortably appointed one and two bedroom vacation rentals with a stocked, full-sized kitchen, queen sized beds, two full bathrooms, and all your linens and paper goods are here on Cape Cod’s bucolic south coast. This is a bonanza of family fun and great amenities including mini golf, sand volleyball, horseshoes and shuffleboard and more for the kids. Two large pools, hot tub, exercise room and two tennis courts for all. Just five miles from Nantucket Sound between Falmouth and Hyannis you’re near South Cape Beach, shopping, art galleries and every kind of adventure. Local marinas provide equipment rentals and fishing charters. Take a day trip to Martha’s Vineyard or Nantucket, or just sit down and have your way with Cape Cod’s best lobster roll.

Edgewater Beach Resort

95 Chase Avenue Dennisport, MA, 02639 Phone: 508-398-6922 Toll-Free: 866-469-8222

A summer escape with an ocean view

A summer with a private beach on the ocean, two pools, great shopping, museums, amusement rides, ice cream, great seafood and golf is a fun filled summer. And it’s all yours at this year round resort on the shores of Nantucket Sound. Vacation rentals including studios and one & two bedroom suites feature ocean views, a gas fireplace, efficiency-sized kitchen and wireless internet service. A host of great children’s activities are available all summer long and the whole family will enjoy the local area and its nearby activities. Walk out your door to the sun and 400 feet of beach that make for a perfect mid-Cape escape. Indoor and outdoor pools, a fitness center and a seven-hole putting green are for when you tire of the rest.

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