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Holiday rentals in Massachusetts

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Top-rated holiday rentals in Massachusetts

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

In town, newly renovated studio with private deck
SUPERHOST
Entire guest house · 2 guests · 1 bed · 1 bathroom

In town, newly renovated studio with private deckCome explore our unique area and stay in a newly renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

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

The Writer's Retreat: A Sweetwater StayLocated 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.

Secret Corner of Shelburne Falls
SUPERHOST
Entire loft · 3 guests · 2 beds · 1 bathroom

Secret Corner of Shelburne FallsA two level loft apartment walking distance to Shelburne Falls. Private, simple, unique, cute, and efficient. The neighborhood is peaceful and quiet with the notable exception of a nearby train intersection. 4-6 times in a given 24 hour period there'll be a loud train whistle. Please see Covid-19 update in "Other things to note..."

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

SUPERHOST
  1. Entire flat
  2. Pepperell
Pepperell, MA: 1 Bdrm Apt at Dragonfly Farm
SUPERHOST
  1. Private room
  2. Hatfield
Cozy farmhouse in 5-college area.
SUPERHOST
  1. Entire flat
  2. Tisbury
Mayflower Haven
SUPERHOST
  1. Entire cottage
  2. Norton
MODERN WATERFRONT COTTAGE*WIFI*NETFLIX*ROWBOAT!
SUPERHOST
  1. Entire flat
  2. Shelburne Falls
Annies’ Place by The Bridge of Flowers ~
  1. Entire guest house
  2. Northampton
Mill River Cottage (pet friendly!)
SUPERHOST
  1. Entire bungalow
  2. Dartmouth
Updated Vintage Bungalow with Incredible Views
SUPERHOST
  1. Entire flat
  2. Hudson
Private Mother-In-Law apartment on the lake!
SUPERHOST
  1. Entire guest suite
  2. Winthrop
Get to The Point and the beach!
SUPERHOST
  1. Entire house
  2. Chester
Riverfront Getaway
SUPERHOST
  1. Entire guest suite
  2. Yarmouth
Sweet Little Suite in South Yarmouth
  1. Entire cabin
  2. Warwick
Artsy Pine Cabin in the Woods