A lake with a rocky shoreline and a forested island.

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Western Massachusetts vacation homes

Property grounds

1. 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 893
AED 1,522 total
includes taxes & fees
31 Aug - 1 Sep
Charming, updated 3 bedroom farmhouse farm stay.
Interior

2. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (61 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 751 total
includes taxes & fees
16 Aug - 17 Aug
Lovely 2nd Floor Apartment
Desk, iron/ironing board, travel crib, WiFi

3. 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
13 Aug - 14 Aug
The Creation Station is a cozy place so make yourself at home.
Property grounds

4. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (148 reviews)
"Great location"
United States
Will G.
The price is AED 698
AED 1,308 total
includes taxes & fees
23 Aug - 24 Aug
Big farmhouse in the foothills of the Berkshires
3 bedrooms, desk, iron/ironing board, travel crib

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

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (16 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is AED 942
AED 1,890 total
includes taxes & fees
17 Aug - 18 Aug
Townhouse with Pool Table - Renovated w/ King Bed
Coffee/tea maker, fridge, microwave, oven

6. Charming 3 bed/2 bath town home with gorgeous back yard

Charming 3 bed/2 bath town home with gorgeous back yard
Forest Park
9.8 out of 10, Exceptional, (15 reviews)
"Clean, comfortable house exactly as described. Easy check-in and responsive host. All amenities worked well and everything we needed was provided. Would stay here again! Highly recommended if you are looking for a place to stay during AAU basketball tournaments - location was central to all the venues."
United States
Barbara W.
The price is AED 2,231
AED 2,894 total
includes taxes & fees
13 Aug - 14 Aug
Charming 3 bed/2 bath town home with gorgeous back yard
House, 4 Bedrooms | Interior

7. Chef's Kitchen Family Basecamp Amherst

Chef's Kitchen Family Basecamp Amherst
3.0 star property
East Village Historic District
The price is AED 1,337
AED 2,490 total
includes taxes & fees
26 Aug - 27 Aug
Chef's Kitchen Family Basecamp Amherst
Coffee/tea maker, fridge, microwave, oven

8. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (53 reviews)
"Our 4th week here and our crew could not be happier with the accommodations"
United States
Maureen A.
The price is AED 1,301
AED 2,717 total
includes taxes & fees
16 Aug - 17 Aug
Spacious 5BR w/ Hot Tub & Games
Property grounds

9. 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 AED 765
AED 1,744 total
includes taxes & fees
28 Aug - 29 Aug
Riverbend Berkshire East Basecamp - 3 bedrooms available
Coffee/tea maker, fridge, microwave, oven

10. Historic Stockbridge Villa on 25 acres

Historic Stockbridge Villa on 25 acres
Stockbridge
10.0 out of 10, Exceptional, (20 reviews)
"Great home, warm and welcoming!! Hosts were great! Very attentive, enjoyed meeting Lisa. Plenty of room for our gathering, accommodations were excellent! "
United States
Amy M.
The price is AED 2,072
AED 4,000 total
includes taxes & fees
17 Aug - 18 Aug
Historic Stockbridge Villa on 25 acres
Interior

11. 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, (6 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 628
AED 1,506 total
includes taxes & fees
9 Sep - 10 Sep
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Coffee/tea maker, fridge, microwave, oven

12. 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 1,012
AED 1,520 total
includes taxes & fees
24 Aug - 25 Aug
Home in Great Barrington
Interior

13. 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 780
AED 1,208 total
includes taxes & fees
19 Aug - 20 Aug
Cozy Riverside Berkshires Retreat
Coffee/tea maker, fridge, microwave, oven

14. Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (21 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 639
AED 1,428 total
includes taxes & fees
19 Aug - 20 Aug
Cozy Home in Holyoke with 3 bedrooms
Outdoor spa tub

15. 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 635
AED 1,513 total
includes taxes & fees
25 Aug - 26 Aug
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Terrace/patio

16. Beautiful 4BR 2 Bathroom House with Parking

Beautiful 4BR 2 Bathroom House with Parking
Forest Park
10.0 out of 10, Exceptional, (14 reviews)
"The hosts were super accommodating. The house was very clean with towels and shower stuff available."
United States
Julia S.
The price is AED 1,469
AED 2,859 total
includes taxes & fees
7 Sep - 8 Sep
Beautiful 4BR 2 Bathroom House with Parking
TV, fireplace, printers

17. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is AED 2,079
AED 4,821 total
includes taxes & fees
13 Aug - 14 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Exterior

18. The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful cabin in a beautiful location. Host is amazing, very responsive. "
United States
Anonymous traveler
The price is AED 1,128
AED 1,832 total
includes taxes & fees
7 Sep - 8 Sep
The Greylock Cabin
4 bedrooms, travel crib, WiFi, bed sheets

19. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is AED 1,868
AED 3,206 total
includes taxes & fees
2 Sep - 3 Sep
Stylish Mid-century Modern Berkshires Cape
Smart TV, books

20. Stylish 4BR 2 Bathroom Home in Forest Park

Stylish 4BR 2 Bathroom Home in Forest Park
Forest Park
10.0 out of 10, Exceptional, (5 reviews)
"Home was a perfect gathering and resting place for our group of employees working in the state buildings at the Big E"
United States
Sharon R.
The price is AED 1,396
AED 2,763 total
includes taxes & fees
13 Aug - 14 Aug
Stylish 4BR 2 Bathroom Home in Forest Park
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Pool and staff was great"
peter 2-night trip
Posted less than an hour ago
Vacation Village in the Berkshires

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