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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.

  • '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:

    “Denise was a wonderful host, and the property was beautiful and serene. The grounds were very well maintained, the house was picturesque and cozy, and its proximity to many small, enjoyable Berkshire towns and trails makes it a very convenient get-away. Denise herself was very friendly and accommodating, giving us much information about the area, and teaching us how to keep warm with the fun pellet stove and mattress warmers. I hope we can revisit soon.”

  • Get to The Point!
    SUPERHOSTEntire guest suite · 2 guests · 1 bed · 1 bathroom
    Get to The Point!

    This cozy one bedroom, private bathroom includes FREE off-street parking, comfy and cozy queen bed with premium linens, nespresso, fridge with complimentary munchies and NO cleaning fee. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area. PLEASE REVIEW CURRENT STATE RESTRICTIONS BEFORE BOOKING AT: https://www.mass.gov/doc/march-31-2020-hotel-motel-guidance/download

    What guests are saying:

    “John and Arturo’s place was perfect. From details like super stylish coffee cups, to super comfy bed and bed linen smelling amazing. Great communication and thoughtful details. Close to water, beach and a place to watch the sunset from. If I ever ran an airbnb, I would want it to be like this.”

  • 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:

    “Patti’s Writer’s Cabin is just one of many properties that she and her family own and manage. All of them seem well appointed and thoughtfully designed with an eye for detail and comfort. This cabin is right off the water, which made for a gorgeous backdrop. Even with some rainy weather, my wife and I had the opportunity to enjoy the deck, fire pit and kayaks during our stay. The cabin was easy to find and Patti provided accurate instructions. The WiFi worked great, which was essential for us both to WFH, and also since there was very spotty reception off the road. We’d be happy to check out another one of their rentals in the future.”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Massachusetts holiday rentals

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

Other great holiday rentals in Massachusetts

Country Charm minutes from the Hub - 1st Floor Apt
SUPERHOSTEntire flat
Country Charm minutes from the Hub - 1st Floor Apt
Price:£39 / night
Traditional Log House Near Cape Cod
SUPERHOSTEntire cabin
Traditional Log House Near Cape Cod
Price:£139 / night
Private and Very Comfortable One-Bedroom Apartment
SUPERHOSTEntire flat
Private and Very Comfortable One-Bedroom Apartment
Price:£51 / night
The Pondhouse - A Magical Place
SUPERHOSTEntire cabin
The Pondhouse - A Magical Place
Price:£199 / night
Romantic Ocean/Boston Views with Exclusive Hot Tub
SUPERHOSTEntire flat
Romantic Ocean/Boston Views with Exclusive Hot Tub
Price:£158 / night
Sweet Brookside Cottage
SUPERHOSTEntire cottage
Sweet Brookside Cottage
Price:£55 / night
Studio Fully Fitted Near Downtown Worc & Clark- U
Entire house
Studio Fully Fitted Near Downtown Worc & Clark- U
Price:£52 / night
Grace's Harborview Fast T Downtown
SUPERHOSTPrivate room
Grace's Harborview Fast T Downtown
Price:£31 / night
Cute love shack in MA's best town by the water
SUPERHOSTEntire bungalow
Cute love shack in MA's best town by the water
Price:£134 / night
Historic Salem Oceanfront 2 Rm Apt
SUPERHOSTEntire flat
Historic Salem Oceanfront 2 Rm Apt
Price:£107 / night
Private Airbnb Apartment in Worcester
SUPERHOSTEntire flat
Private Airbnb Apartment in Worcester
Price:£48 / night
★ Spacious & Modern ★ Professionally Sanitized ★
SUPERHOSTPrivate room
★ Spacious & Modern ★ Professionally Sanitized ★
Price:£35 / night
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