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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.

Serene Artist's Cottage with Mountain Views
SUPERHOST
Entire cottage · 2 guests · 1 bed · 1 bathroom

Serene Artist's Cottage with Mountain ViewsNewly designed and constructed artist's cottage situated on 5 private acres with a 40 mile view to the east (and Mount Monadnock), private pond, perennial gardens, outdoor shower, full bath, cook's kitchen, and access to all the best of Western Massachusetts and beyond. 5 minutes by car to Heath Fair; 15 mins. to Charlemont & Zoar Outdoor; 15 mins. to Shelburne Falls, 45 mins. Northampton; 40 minutes to MASS MoCA; 50 minutes to Brattleboro, VT.

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

SUPERHOST
  1. Entire flat
  2. Pepperell
Pepperell, MA: 1 Bdrm Apt at Dragonfly Farm
₹6,933 per night
SUPERHOST
  1. Entire flat
  2. Westborough
Private and Very Comfortable One-Bedroom Apartment
₹4,827 per night
SUPERHOST
  1. Entire cottage
  2. Norton
MODERN WATERFRONT COTTAGE*WIFI*NETFLIX*ROWBOAT!
₹12,771 per night
SUPERHOST
  1. Entire cabin
  2. Hubbardston
Triggers Cabin
₹7,485 per night
  1. Entire guest house
  2. Northampton
Mill River Cottage (pet friendly!)
₹6,933 per night
SUPERHOST
  1. Entire cottage
  2. Orange
The Photographer's Hut: A Sweetwater Stay
₹8,778 per night
SUPERHOST
  1. Entire guest suite
  2. Winthrop
Get to The Point and the beach!
₹6,307 per night
SUPERHOST
  1. Entire house
  2. Chester
Riverfront Getaway
₹10,603 per night
SUPERHOST
  1. Entire guest suite
  2. Yarmouth
Sweet Little Suite in South Yarmouth
₹7,506 per night
SUPERHOST
  1. Entire flat
  2. Hopedale
A peaceful retreat on the pond.
₹6,245 per night
  1. Private room
  2. North Adams
North Adams- Spacious Bedroom with private bath
₹6,213 per night
SUPERHOST
  1. Entire loft
  2. Shelburne Falls
Secret Corner of Shelburne Falls
₹6,380 per night