Vacation home rentals in Massachusetts

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Top-rated vacation home rentals in Massachusetts

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Top guest favorite
A spacious outdoor deck is showcased, featuring a wooden dining table with benches and a grill. The house's shingle exterior is prominently displayed. Large glass doors provide access to the interior, while an upper balcony offers additional outdoor space and views of the surrounding scenery.
Vacation home in East Sandwich
4.94 out of 5 average rating, 78 reviews

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!

Top guest favorite
The exterior of a Victorian-style building is shown, featuring multiple gabled roofs and spacious windows. Lush green lawns surround the property, with flowering plants and large rocks integrated into the landscape. The ocean is visible in the background, enhancing the coastal setting.
Vacation home in Gloucester
5 out of 5 average rating, 70 reviews

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.

Top guest favorite
The exterior of the home is showcased, featuring a spacious backyard with a rectangular pool and lounge seating. The light-colored stone facade is complemented by large windows. An expansive green lawn surrounds the area, with a patio leading to the entrance of the house.
Vacation home in Sandwich
4.97 out of 5 average rating, 33 reviews

Home in Sandwich with 5 star Resort Amenities

Looking for a luxurious getaway w/ amenities you can only dream of, located near trails on conservation behind the house, beaches (10min drive)& ponds(2min drive) on Cape Cod? Look no more! Lavish in opulence w/ top amenities of a 5-star resort made entirely available to you all in one place. Relax & unwind w/ saltwater pool, enjoy a game of volleyball, or cook outdoors while the kids play in the playground. S'mores anyone? Unite all around the fire pit! U can truly live the way you dream.

Guest favorite
A two-story gray house is situated near the water, surrounded by trees. A stone wall leads to a sandy beach, with wooden stairs providing access. Outdoor seating is visible on a patio, inviting relaxation in the serene setting.
Vacation home in Mashpee
4.92 out of 5 average rating, 50 reviews

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.

Guest favorite
The image captures a charming cape style house with a wooden deck, surrounded by green grass and trees. A low stone wall runs in the foreground, and the evening sky is filled with soft clouds, suggesting a serene atmosphere. The house features multiple entries and a welcoming layout.
Vacation home in Westport
4.93 out of 5 average rating, 29 reviews

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

Top guest favorite
An open concept living area features a comfortable white couch and armchair, with a wooden coffee table at the center. The kitchen, visible in the background, is well-equipped and includes a fridge, while a dining area with two stools is highlighted. Natural light brightens the space.
Vacation home in Chatham
5 out of 5 average rating, 64 reviews

Beautiful Downtown Chatham 1 Bed, Near Oyster Pond

This gorgeous home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, restaurants, the beach, a movie theater, Veterans Field for summer Chatham A’s games, The Squire, & more! This cozy, modern, & newly renovated apartment is ideal for a couple or two friends with an open living room & kitchen space + private patio. 1 Min Walk to Downtown Chatham 9 Min Walk to Oyster Pond Beach Experience Chatham with us & Learn More Below!

Guest favorite
The image captures a serene lakefront view, showcasing lush greenery surrounding a secluded house. A wooden dock extends into the calm water, providing access to the lake, while the sunlit landscape emphasizes the tranquility of the natural setting.
Vacation home in Becket
4.97 out of 5 average rating, 61 reviews

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!

Guest favorite
A two-story coastal home is portrayed, featuring a shingled exterior and multiple windows. A gravel driveway is visible in the foreground, with greenery and sandy areas surrounding the house. Power lines run overhead against a clear blue sky.
Vacation home in Marshfield
4.96 out of 5 average rating, 109 reviews

Shoreline Serenity: Your Coastal Escape Marshfield

5 Bedrooms & 3 Full Bathrooms, washer/dryer & granite kitchen. All essentials in the kitchen. Regular & Keurig coffee maker. We provide bed sheets & blankets, hand/bath and beach towels however please bring your own beach chairs. Private Parking for up to 6 cars. Gas Grill (gas provided) out side fire pit (please bring your own wood), chairs and picnic tables. Brand new Central Aircondition June 2017. Winter Rental available, please inquire if interested.

Top guest favorite
Vacation home in Randolph
4.98 out of 5 average rating, 100 reviews

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.

Top guest favorite
A charming home is set against a clear blue sky, surrounded by lush greenery and colorful flowering shrubs. The front porch features seating and a light blue door, while several adirondack chairs are positioned in the yard, creating inviting outdoor spaces.
Vacation home in Dennis
4.96 out of 5 average rating, 52 reviews

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.

Guest favorite
A private entrance is approached by a pathway lined with gravel and natural stones, leading to a wooden deck. The home features a modern grey exterior, complemented by a lush green lawn and a large tree, providing a serene and tranquil setting.
Vacation home in Great Barrington
4.94 out of 5 average rating, 263 reviews

Home in Great Barrington. Steps from downtown!

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. 🫶

Guest favorite
A cozy living area features a large red leather sectional sofa and two modern red chairs. A glass coffee table is positioned on a patterned area rug. Natural light enters through three windows adorned with light curtains, while a ceiling fan adds functionality to the space.
Vacation home in Winthrop
4.92 out of 5 average rating, 101 reviews

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.

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