A lake with a rocky shoreline and a forested island.

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Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Western Massachusetts vacation homes

Interior

1. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (64 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 AED 426
AED 743 total
includes taxes & fees
7 Sep - 8 Sep
Lovely 2nd Floor Apartment
Desk, iron/ironing board, travel crib, WiFi

2. 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 AED 661
AED 1,034 total
includes taxes & fees
14 Sep - 15 Sep
The Creation Station is a cozy place so make yourself at home.
Property grounds

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 AED 932
AED 1,560 total
includes taxes & fees
7 Sep - 8 Sep
Charming, updated 3 bedroom farmhouse farm stay.
Interior

4. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 536
AED 1,378 total
includes taxes & fees
7 Sep - 8 Sep
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Outdoor spa tub

5. 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 AED 588
AED 1,445 total
includes taxes & fees
7 Sep - 8 Sep
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very Good, (1 review)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is AED 195
AED 1,071 total
includes taxes & fees
13 Sep - 14 Sep
Real Estate: Therapy - Lake, Laundry, Love it
Coffee/tea maker, fridge, microwave, oven

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 AED 661
AED 1,436 total
includes taxes & fees
7 Sep - 8 Sep
Cozy Home in Holyoke with 3 bedrooms
Property grounds

8. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (150 reviews)
"Great location"
United States
Will G.
The price is AED 698
AED 1,293 total
includes taxes & fees
7 Sep - 8 Sep
Big farmhouse in the foothills of the Berkshires
Iron/ironing board, WiFi, bed sheets

9. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is AED 591
AED 1,342 total
includes taxes & fees
7 Sep - 8 Sep
Cozy private 2 bed apartment in Shelburne Falls
Exterior

10. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is AED 441
AED 784 total
includes taxes & fees
8 Sep - 9 Sep
Private bed with En-suite bathroom Marigold Room
Interior

11. 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 AED 685
AED 1,384 total
includes taxes & fees
13 Sep - 14 Sep
Linny's - Private Dock - Lake Access - Firepit
3 bedrooms, desk, iron/ironing board, travel crib

12. 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 AED 879
AED 1,806 total
includes taxes & fees
15 Sep - 16 Sep
Townhouse with Pool Table - Renovated w/ King Bed
Private kitchen

13. Guest B&B Close to the MgM, Basketball Hall of fame, and downtown springfield.

Guest B&B Close to the MgM, Basketball Hall of fame, and downtown springfield.
Liberty Heights
5.0 out of 10, (2 reviews)
"Good location, everything clean, couple stores near by, good parking, the only issue was one AC unit wasn’t working at all on that ne bedroom besides that everything was good, very good communication with the owner."
United States
Isis
The price is AED 661
AED 1,196 total
includes taxes & fees
6 Sep - 7 Sep
Guest B&B Close to the MgM, Basketball Hall of fame, and downtown springfield.
Smart TV, fireplace, video games, books

14. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield
Forest Park
9.6 out of 10, Exceptional, (46 reviews)
"It was nice stay!"
United States
Lorrie
The price is AED 661
AED 1,329 total
includes taxes & fees
7 Sep - 8 Sep
Cozy & Spacious Entire Home in Springfield
Smart TV, fireplace, books

15. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (7 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 AED 1,010
AED 2,462 total
includes taxes & fees
7 Sep - 8 Sep
5BR Berkshire Home Mins To The Mountain
Smart TV

16. Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield

Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Boston Road
8.6 out of 10, Excellent, (19 reviews)
"Location was perfect for us; 10 minutes from family. Host was responsive; we had a lovely stay in Springfield."
United States
Beth P.
The price is AED 661
AED 1,450 total
includes taxes & fees
8 Sep - 9 Sep
Cozy 3-bedroom Duplex1 with WiFi, AC in peaceful Springfield
Coffee/tea maker, fridge, microwave, oven

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 AED 876
AED 1,352 total
includes taxes & fees
8 Sep - 9 Sep
Home in Great Barrington
Interior

18. 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 AED 744
AED 1,163 total
includes taxes & fees
8 Sep - 9 Sep
Cozy Riverside Berkshires Retreat
Coffee/tea maker, fridge, microwave, oven

19. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (55 reviews)
"This is the second time we have stayed at this property. It is very spacious, cozy, and clean. The beds are very comfortable. It had everything we needed "
United States
Staci M.
The price is AED 1,079
AED 2,411 total
includes taxes & fees
8 Sep - 9 Sep
Spacious 5BR w/ Hot Tub & Games
Smart TV

20. 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 AED 684
AED 1,264 total
includes taxes & fees
7 Sep - 8 Sep
Beautifully Renovated First-Floor Apartment Getaway
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

Hotel UMass

Hotel UMass

8/10 Good
"The Manager was exceptionally kind and helpful to me September 4, 2026. Commendable!"
India 1-night trip
Posted 5 hours ago
Hotel UMass

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