A lake with a rocky shoreline and a forested island.

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Western Massachusetts vacation homes

A cozy room with two beds, large windows, and a view of a snowy landscape.

1. The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (77 reviews)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
United States
Paula
The price is ￥28,613
￥43,147 total
includes taxes & fees
Sep 14 - Sep 15
The Creation Station is a cozy place so make yourself at home.
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

2. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (62 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is ￥18,371
￥32,363 total
includes taxes & fees
Sep 1 - Sep 2
Lovely 2nd Floor Apartment
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

3. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (41 reviews)
"Great hosts! Very nice and helpful. "
United States
Anonymous traveler
The price is ￥38,450
￥65,561 total
includes taxes & fees
Sep 1 - Sep 2
Charming, updated 3 bedroom farmhouse farm stay.
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

4. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is ￥9,697
￥47,763 total
includes taxes & fees
Sep 13 - Sep 14
Real Estate: Therapy - Lake, Laundry, Love it
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

5. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (7 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥26,228
￥63,922 total
includes taxes & fees
Sep 9 - Sep 10
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A hot tub with a string of lights above it, set against a dark night sky.

6. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ￥25,465
￥63,069 total
includes taxes & fees
Aug 25 - Aug 26
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A modern kitchen with stainless steel appliances, a granite countertop, and a view into the dining area.

7. Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (22 reviews)
"Fantastic stay in Holyoke. House is close to town, well outfitted, and super clean. Easy check in process and great experience all around. "
United States
Grant J.
The price is ￥27,818
￥61,969 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Home in Holyoke with 3 bedrooms
A house with a porch, a garden with pink flowers, and a stone wall along the road.

8. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (149 reviews)
"Great location"
United States
Will G.
The price is ￥30,064
￥56,363 total
includes taxes & fees
Sep 2 - Sep 3
Big farmhouse in the foothills of the Berkshires
A hallway with wooden flooring, white walls, and a bed in the background.

9. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is ￥25,475
￥57,797 total
includes taxes & fees
Sep 17 - Sep 18
Cozy private 2 bed apartment in Shelburne Falls
A bedroom with a bed, curtains, a bedside table, and a lamp.

10. Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (17 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is ￥37,054
￥76,845 total
includes taxes & fees
Aug 25 - Aug 26
Townhouse with Pool Table - Renovated w/ King Bed
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

11. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is ￥19,075
￥34,268 total
includes taxes & fees
Sep 9 - Sep 10
Private bed with En-suite bathroom Marigold Room
A modern kitchen with white cabinets, a wooden staircase, and a dining area with a table and chairs.

12. Chef's Kitchen Family Basecamp Amherst

Chef's Kitchen Family Basecamp Amherst
3.0 star property
East Village Historic District
The price is ￥57,601
￥107,289 total
includes taxes & fees
Sep 3 - Sep 4
Chef's Kitchen Family Basecamp Amherst
A spacious kitchen with a large island, wooden beams, and pendant lighting.

13. Linny's - Private Dock - Lake Access - Firepit

Linny's - Private Dock - Lake Access - Firepit
West Suffield
10.0 out of 10, Exceptional, (43 reviews)
"Perfect, relaxing and easy!"
United States
Wendy C.
The price is ￥32,425
￥64,014 total
includes taxes & fees
Sep 13 - Sep 14
Linny's - Private Dock - Lake Access - Firepit
A modern living room with a white sofa, a coffee table, and a red and black rug. There is a staircase with a white railing leading to a second floor.

14. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield
Forest Park
9.6 out of 10, Exceptional, (45 reviews)
"It was nice stay!"
United States
Lorrie
The price is ￥26,467
￥54,916 total
includes taxes & fees
Aug 25 - Aug 26
Cozy & Spacious Entire Home in Springfield
A wooden deck with two chairs and a table, overlooking a green landscape with a tree and hills.

15. Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (5 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is ￥33,103
￥75,488 total
includes taxes & fees
Aug 28 - Aug 29
Riverbend Berkshire East Basecamp - 3 bedrooms available
A living room with a brown leather sofa, two grey armchairs, a glass coffee table, and a wooden side table with a lamp.

16. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (4 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is ￥27,500
￥63,566 total
includes taxes & fees
Sep 14 - Sep 15
stylish Berkshires Retreat
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

17. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is ￥42,919
￥64,631 total
includes taxes & fees
Aug 25 - Aug 26
Home in Great Barrington
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

18. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (6 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is ￥43,714
￥105,826 total
includes taxes & fees
Aug 23 - Aug 24
5BR Berkshire Home Mins To The Mountain
A modern living room with a black leather sofa set, a glass coffee table, and a patterned rug.

19. Beautifully Renovated First-Floor Apartment Getaway

Beautifully Renovated First-Floor Apartment Getaway
Forest Park
9.2 out of 10, Wonderful, (5 reviews)
"This was a spacious 4 bedroom. Clean and smooth check in and out. Thank you for having me and my guest "
United States
Alyssa A.
The price is ￥28,613
￥53,562 total
includes taxes & fees
Aug 22 - Aug 23
Beautifully Renovated First-Floor Apartment Getaway
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

20. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is ￥32,189
￥49,983 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Riverside Berkshires Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Western Massachusetts Hotel Reviews

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Lovely property! Every staff member was so helpful and professional! We will be back!"
Bonnie 2-night trip
Posted less than an hour ago
D. Hotel Suites & Spa

Find out more about Western Massachusetts

Western Massachusetts Vacation Homes information

Number of reviews
501
Accommodation
463 Vacation Homes
Lowest Price
￥32,363
Highest Price
￥107,289

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