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Vacation rentals in Massachusetts

Vacation rentals in Massachusetts

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Massachusetts

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • The Writer's Retreat: A Sweetwater Stay
    SUPERHOSTEntire cottage · 2 guests · 1 bed · 1 bathroom
    The Writer's Retreat: A Sweetwater Stay

    Located on the shore of Tully Pond, The Writers Retreat is a newly designed 325sqft lake side cottage with breathtaking views of Tully Mountain. This 4-season cottage is built with salvaged barn wood; up-cycled maple floors and custom built furniture and lighting. It's the little sister to The Fishing Cottage. You'll find this intimate home has everything you need to relax, write the next Great American Novel, connect with a lover, or just plain chill. Note: landscaping is a work-in-progress.

    What guests are saying:

    “The Writers' Retreat really has everything for a romantic getaway or just a change of scenery while you're working remotely. I stayed here for 5 days with my husband and dog for our first anniversary, and we had a blast. It looks small at first, but it was designed very efficiently and we never felt crowded or cramped. There was plenty of storage for all our stuff so we didn't have to live out of a suitcase, and between the kitchen, bedroom, spacious bathroom, living room area, and huge porch, there was more than enough space for us to pass the time together or apart. The rustic/industrial salvage style is really fun and interesting, and there are unique little touches everywhere. The kayaks, grill, and fire pit are always available and self-serve, which made it easy to stay entertained outdoors. We enjoyed playing cards on the deck, spotting turtles out on the pond, and taking the dog for long walks down the country road or for a dip in the water. At night, we would sit around the fire with a glass of wine and watch the sun set on the pond, then cuddle up on the loveseat and stream a movie (both rooms have smart TVs, and the internet connection was flawless so it was easy to cast anything you want to watch from your phone without having to bring a Chromecast or log in to anything). We had to work remotely for some of our trip, but between the laptop station in the bedroom and the large breakfast bar in the kitchen, we felt as if we each had our own private office - which is honestly more than we get at home! And with views of the water from every seat, we never felt like we were cooped up inside. There were plenty of power outlets all over the house, and on the deck, so you could sit outside all day and still be productive! Patti was always very friendly and helpful if we had a question or ran out of something like salt or coffee. We can't wait to visit again, or maybe try one of the other Sweetwater Stays!”

  • 'Silo Studio' Cottage
    SUPERHOSTEntire guest house · 2 guests · 1 bed · 1 bathroom
    'Silo Studio' Cottage

    Charming and romantic,' Round' Cottage on the Santarella Estate in the Berkshires in Western Massachusetts. Formerly, the cottage was sculptor Henry Hudson Kitson's summer studio on the Santarella Estate. The two-story cottage has a charming bedroom with 35 foot high conical ceiling with canopied bed upstairs with views through massive, multi-paned "mill windows" to the trees and sky and out to the lily pond. The downstairs sitting room looks out on the babbling brook and lovely gardens.

    What guests are saying:

    “Like straight out of a fairytale, Santarella, and the Silo Studio specifically, are nothing short of awe inspiring! You will not be disappointed with your stay! If I had to describe the place in 3 words they would be: idyllic, romantic, fantastic!”

  • The Annex Oceanfront
    SUPERHOSTEntire guest suite · 2 guests · 2 beds · 1 bathroom
    The Annex Oceanfront

    The Annex is the walk-in cellar apartment of a private home, with neighboring houses close-by. It has its own entrance, with a cemented patio which is part of the seawall. My daughter and I share the house, so it is owner-occupied...along with her dog, Luigi. Although there isn't a stove in the unit, there is a neighborhood restaurant. We are located 30 minutes from Boston. Off street parking is available for one car only. Prices are based on 2 guests.

    What guests are saying:

    “Edie's home is better than the pictures. My husband and I truly enjoyed our time in Nahant and even better having the view and beach just yards away. The Tides Restaraunt and Dunkin Donuts was also extremely convenient. Edie allowed us to check in early and was accomodating on my family's parking. Home was absolutley beautiful, quiet and comfortable for the two of us. All necessities are provided including beach towels and chairs, coffee, Wifi and cable TV. Bed and linens were perfect. Thank you again and I hope we make it back that way.”

Holiday rentals for every style

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Popular amenities for Massachusetts holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Massachusetts

Riverfront Getaway
SUPERHOSTEntire house
Riverfront Getaway
Price:€137 / night
Barn Cottage on Minister Pond
SUPERHOSTEntire cottage
Barn Cottage on Minister Pond
Price:€69 / night
Contemporary Lakeside Retreat
SUPERHOSTEntire house
Contemporary Lakeside Retreat
Price:€132 / night
Lakeside cottage, "Breezy Point"
Entire cottage
Lakeside cottage, "Breezy Point"
Price:€195 / night
Stunning ocean views, stairs down to the beach
SUPERHOSTEntire cottage
Stunning ocean views, stairs down to the beach
Price:€372 / night
The Pondhouse - A Magical Place
SUPERHOSTEntire cabin
The Pondhouse - A Magical Place
Price:€233 / night
The Woodbourne - Prvt JP 2BR 15 Min To Everywhere!
SUPERHOSTEntire flat
The Woodbourne - Prvt JP 2BR 15 Min To Everywhere!
Price:€114 / night
The Farm House, with a hot tub!
SUPERHOSTEntire house
The Farm House, with a hot tub!
Price:€186 / night
Cottage facing fresh water pond
SUPERHOSTEntire guest house
Cottage facing fresh water pond
Price:€119 / night
Agawam In-Law Suite *Casino,Airport,6 Flags,Big E
SUPERHOSTEntire house
Agawam In-Law Suite *Casino,Airport,6 Flags,Big E
Price:€74 / night
Get to The Point and the beach!
SUPERHOSTEntire guest suite
Get to The Point and the beach!
Price:€82 / night
Octagonal Glass Treehouse in Berkshires
SUPERHOSTEntire chalet
Octagonal Glass Treehouse in Berkshires
Price:€202 / night
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