
Holiday home rentals in Massachusetts
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Top-rated holiday home rentals in Massachusetts
Guests agree: these holiday home rentals are highly rated for location, cleanliness and more.

Oceanfront Home on Private Beach!
Make unforgettable memories at this oceanfront escape, just steps from a private beach. Sanctuary is a 4 bed, 3 bath home built into the dunes—perfect for families, groups, and beach lovers. Designed for comfort and connection, it’s loaded with amenities and space for everyone to unwind. Minutes from shops, restaurants, breweries, and the iconic Sandwich Boardwalk. Easy access to downtown and Routes 6 & 6A makes getting around a breeze. Soak up the best of Cape Cod—your coastal getaway awaits!

Gorgeous Oceanfront 2-Bdrm Apartment w/ Fireplace
Spectacular, furnished 2-bedroom apartment is just moments from the North Shore's iconic Good Harbor Beach, Bass Rocks Golf Club, colorful Rocky Neck & historic Gloucester with its storied seaport & burgeoning cultural & dining scene. This beautifully renovated oceanfront apartment rental makes the most of its spectacular setting in a 2-unit Victorian home with 2 bedrooms (1 King & 1 Queen), 1 1/2 bathrooms, fireplaced living room w/ Queen sofa bed, quartz kitchen countertops & laundry in unit.

Private Beach Haven on Seconsett Island
This charming 4-bed, 2-bath Cape house on Seconsett Island is an ideal retreat for those seeking a memorable Cape Cod experience. Nestled in a perfect location, it offers breathtaking views and exclusive access to a private beach. Whether you're into activities like clam digging, kayaking, swimming in the ocean, or exploring the coastline with our powerboat. Book your stay now and embark on an unforgettable adventure. Create memories that will last a lifetime in this picturesque setting.

Spacious 4BR Home near Water Park, Pond & Beaches
This lovely Cape home is perfect for your family. It's located in the heart of Buzzards Bay, close to the Sagamore and Borne Bridge. You can reach Electric Avenue Beach in just 5 minutes by car. If you prefer something different, Queen Sewell Pond is nearby, with a kids-friendly beach overlooking the water. The house has 4 bedrooms and is packed with amenities like a dry bar, fire pit, charcoal and gas grill, and more. It's a great place to create lasting memories with your loved ones.

FarmCoast FarmHouse: Close to Beach, Amazing Views
Take it easy at this unique and tranquil getaway. This one bedroom plus den unit is in one of the most coveted areas of the South Coast of Massachusetts. Located just off the Westport river, surrounded by farmland, this house is only ten minutes to several beaches and five minutes from the center of town. Newly renovated, this unit is one of two units within a cape style house built in 1823. Includes a large back deck, grill, and outdoor fireplace/chiminea. 1 bed plus den w/ pullout

Home in Great Barrington. Steps from downtown!
First Things First… Let’s Keep the Love Alive! ❤️ 🙌 Central and Private! Just steps away from historic downtown Great Barrington. East Mountain Hiking trails are a quick walk away. Enjoy sunset views with friends and family, before you walk into town for a night out! Butternut Ski Area: 5-10 min drive(traffic depending) Tanglewood: 20-25 min This new home features all new appliances and furniture. Enjoy luxury, charm, and privacy while you rest easy at The Maple. 🫶

The Lake
Welcome to Lake Congamond's North Pond! Wake up every day just steps from the water. Grill out on the brand new Trex deck with stunning water views, and dock your boats for the duration of your stay. This home features ample parking, central air, cornhole boards, an outdoor dartboard, and a propane-fueled fire pit. The location is great as the house is just minutes away from Bars, Restaurants, and Golf Courses. This vacation rental truly has it all! Book your stay today!

Perfect Serene Waterfront All Season Retreat!
Enjoy everything the Berkshires has to offer from this beautiful, secluded, nicely renovated waterfront house set on two wooded acres of forested land. Explore the stream that runs through the property, or just sit on the large deck or down by the crystal clear lake and listen to the sounds of nature while feeling the warm sun on your face. Very private--just one near neighbor. The sunny house has 2 bedrooms, study with sofa bed, 2 full baths, full kitchen!

Built 2020 Private Home/4 Beds/2.5 Baths/EV Charge
Kick back and relax in this calm, stylish brand new built, single home. 15-20 minutes drive to downtown Boston, Encore Casino, China Town. Boston Logan International Airport in 20-25 minutes with moderate traffic. 5 minutes drive to Park & Ride to Airport, 110 Grill, Legal Seafood, Five Guys, Starbucks, LA Fitness, TGI Friday, Bank of America, AMC movie theater, South Shore Shopping Mall, 10 minutes to Chase Bank, BJ, Costco, Kohl’s, Olive garden.

Family Getaway, Modern 5BR, walk to the beach
Bring the whole family to this great place with lots of room for fun. This gorgeous home has 5 bedrooms with 2 baths. Short walk 0.4 miles to Glendon Beach. This house has a new kitchen, stainless steel appliances, and hardwood floors. It's an open floor plan with an oversized family room with a 50" smart flatscreen TV that opens to a private covered flagstone patio with a gas grill and outdoor picnic table. The yard is huge and has a firepit.

Sunny, spacious 3 BR on Winthrop beach
Two steps to the beach! Sunny and spacious 3 bedroom 1st floor condo. The 3 bedrooms are setup with a queen and two full size beds. Two additional twin size beds can be setup in the one of the other rooms. Open floor layout with a spacious living room, dining room and eat in kitchen. Easy self check-in, plenty of parking and close to public transportation.

On the Water Gem - 2 BR -The Cove Lanesville
Enjoy our immaculate 2 BR at The Cove Lanesville, on lovely Ipswich Bay. Two spacious decks overlook spectacular sunsets. You can be as active...or as chill as you desire; great restaurants, world-renowned beaches, shopping, Everything in the Arts, woodland quarry walks. No matter what the season the beauty of this special island does not disappoint.
Popular amenities for holiday home rentals in Massachusetts
Family-friendly holiday home rentals

The Costal Corner - Martha's Vineyard

Built 2020 Private Home/4 Beds/2.5 Baths/EV Charge

Beautiful Family Friendly House with Pool

FarmCoast FarmHouse: Close to Beach, Amazing Views

Home in Great Barrington. Steps from downtown!

NEW***Cozy Cape Family Getaway~A/C ~Screened Porch

Private Beach Haven on Seconsett Island

On the Water Gem - 2 BR -The Cove Lanesville
Holiday home rentals with a patio

Oceanfront location with amenities

Gorgeous historic home sleeps 8 walk to everything

Winterberry Lodge: Newly Renovated at Jiminy Peak

Perfect Cape Getaway, Pool, A/C, Bike Path

Spacious, newly updated condo

Charming 3b/2ba House close to Downtown/Pier/Beach

NEW! Renovated Family-Friendly Vineyard Haven Home

Fabulous Falmouth Heights home steps to beach!
Holiday home rentals with a washing machine and dryer

3 min walk to beach. 1/2 mile to downtown Hyannis.

Explore the Berkshires from this charming home.

2Br w/pack n play, beach gear, close to beach&town

Bright 3 bdrm 2 bath on Bike Trail, 5 min to Beach

New 3 bed condo w/ parking close to everything!

Rare Ocean Edge House - Sleeps 8

Sunny oasis in the woods in Otis

Beautiful Martha's Vineyard Home
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