Holiday Homes in Massachusetts

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!

Location · Family · Walkability

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.

Value · Family · Nearby

Rare Ocean Edge House - Sleeps 8

Brand new listing at Ocean Edge in The Villages! Recently purchased and renovated, this standalone home is located at the end of a lovely cul-de-sac with backyard patio, resort amenities and direct access to the Cape Cod Rail Trail. Home includes fully equipped kitchen, two bedrooms, two full baths, living room, dining area, and large loft that sleeps four. Homeowners are golf-members at Ocean Edge, so renters may get sponsored guest passes to access the resort amenities for a small add-on fee.

Family · Location · Walkability

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!

Family · Location · Amenities

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.

Family · Value · Check-in

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!

Location · Family · Check-in

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.

Value · Family · Checkout

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.

Location · Family · Kitchen

New 3 bed condo w/ parking close to everything!

Enjoy this bright, centrally-located home less than a block from the beach and Commercial St. in Ptown’s West End. Second floor unit includes three beds, one bath and common living spaces. Enjoy the back deck for morning coffee/tea, meals and lounging. Off street parking is available for your use. *Please note July 11th to September 5th 2026 only weekly rentals Saturday to Saturday are permitted.*

Family · Location · Quiet

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.

Location · Family · Kitchen

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.

Value · Family · Kitchen

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.

Location · Value · Long stay