Holiday Homes in Massachusetts

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Top-rated Holiday Homes in Massachusetts

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Top Guest favourite
The exterior of the Oceanfront home is showcased, featuring a multi-level deck with railings and a welcoming entrance. A wooden pathway leads to the house, surrounded by natural grasses and coastal vegetation. The home is constructed with weathered wood siding, reflecting a coastal aesthetic.
Holiday home in Sandwich

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!

4.95 out of 5 average rating, 96 reviews
Top Guest favourite
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.
Holiday home in Gloucester

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.

4.99 out of 5 average rating, 87 reviews
Superhost
A modern Cape house is situated on a spacious lawn, framed by tall trees. The two-story structure features a mix of large windows and a composite siding exterior. A patio area is visible, complemented by simple chairs, and a view of the water is seen in the distance.
Holiday home in Mashpee

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.

4.85 out of 5 average rating, 60 reviews
Guest favourite
An aerial view captures the waterfront property by Waquoit Bay, surrounded by lush greenery. The sandy beach gently curves along the water's edge, with a small dock visible in the bay. A colorful sky at sunset adds a serene backdrop to the scene.
Holiday home in Falmouth

2 Acre Waterfront Oasis Overlooking Waquoit Bay

Perched over sparkling Waquoit Bay, this stylishly renovated waterfront home features a 38’ Living and dinning room. Open plan with large picture windows for watching boats, wildlife, and extraordinary sunsets. Entertain while cooking for the whole family in the large luxury kitchen surrounded by barstool seating. Walk down the path to the bay to swim, fish, paddle board, or kayak. Enjoy magnificent sunsets while grilling, sitting around the fire pit or enjoying the hot tub.

4.94 out of 5 average rating, 81 reviews
Guest favourite
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.
Holiday home in Marshfield

Shoreline Serenity: Your Coastal Escape Marshfield

All 5 Bedrooms are on 2nd floor & 2 Full Bathrooms, on first floor 1 full bathroom and washer/dryer & granite kitchen. All essentials in the kitchen. Regular & Keurig coffee maker. We provide bed sheets & blankets, hand/bath and beach towels. Central Aircondition. Private Parking for up to 6 cars. Gas Grill (gas provided) out side fire pit (please bring your own wood), outdoor seating. Please bring your own games. Winter Rental available, please inquire if interested.

4.96 out of 5 average rating, 114 reviews
Guest favourite
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.
Holiday home in Becket

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!

4.95 out of 5 average rating, 66 reviews
Guest favourite
An open living area is illustrated, featuring a light-colored sectional sofa with blue accent pillows. A large flat-screen television is mounted on the wall. A wooden coffee table sits on a patterned area rug, while a dining area is visible in the background.
Holiday home in Randolph

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

Kick back and relax in this calm, quiet & stylish single new built home. Within 20-25 minutes driving distance to Boston downtown, Logan International Airport, Encore Casino, China Town, Financial District. 5-10 minutes away from Park & Ride shuttle to The Airport, 110 Grill, Legal Seafood, Five Guys, Starbucks, LA Fitness, Tavern in The Square, Bank of America, AMC movie theater, South Shore Shopping Mall, Chase Bank, BJ or Costco, Kohl’s, Olive garden.

4.96 out of 5 average rating, 115 reviews
Top Guest favourite
Holiday home in Falmouth

Fabulous Falmouth Heights home steps to beach!

Falmouth Heights beach is at the end of our street. 5 min walk to Shipwrecked beach bar & restaurant, The Old Casino, Vineyard Ferries, Falmouth Road Race finish line. 1 mile Raw Bar/Boathouse, 1.5 miles Main Street restaurants/shops. Enjoy a relaxing fall, winter or spring getaway in our comfortable Falmouth home, perfectly suited for families, friends, wedding weekends, holiday gatherings and extended stays.

4.96 out of 5 average rating, 49 reviews
Guest favourite
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.
Holiday home in Winthrop

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.

4.92 out of 5 average rating, 124 reviews
Top Guest favourite
A vibrant sunset illuminates the sky with shades of purple and orange, casting a warm glow over the serene water and landscape. Silhouettes of trees frame the scene, offering a picturesque view of the evening sky's colors reflecting on the calm waters.
Holiday home in Gloucester

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.

4.99 out of 5 average rating, 94 reviews
Superhost
The exterior of a cozy cottage features a light blue door and matching shutters. Two adirondack chairs sit on a grassy area in front of the home, with a wooden fence partially visible. A flag can be seen hanging beside the entrance.
Holiday home in West Yarmouth

Oyster Cottage - Cape Escape

Enjoy the tiny home experience in our cozy cottage located in West Yarmouth. Cottage has free parking, a new central A/C and outdoor hot shower. We are close to shops and restaurants, water park and golf course. Beautiful Seagull Beach is a 5 minute drive, 9 minute bike ride or a 30 minute walk through a picturesque neighborhood.

4.94 out of 5 average rating, 52 reviews
Superhost
The open living area includes two couches positioned facing each other, with a small side table nearby. Light wood flooring extends to a dining area featuring a white table and chairs. Soft natural light is visible through the windows, highlighting the light-colored walls.
Holiday home in Brewster

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

Quiet 3 bedroom 2 bathroom on cul-de-sac, with outdoor dining and patio, peaceful sunporch, front lawn seating, with outside shower. Home is equipped with multiple areas for remote working, and has excellent access -- steps to Cape Cod Rail Trail, 5 min to beach, and minutes to Ocean Edge Resort.

4.77 out of 5 average rating, 13 reviews

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