Western Massachusetts Vacation Rentals

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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Western Massachusetts vacation rentals

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Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,335 reviews)
"Clean rooms, and very friendly staff"
United States
Amr
The price is ￥13,694
￥17,038 total
includes taxes & fees
May 17 - May 18
Vacation Village in the Berkshires
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (53 reviews)
"Very clean, cozy and lots of nice plants! "
United States
Mary
The price is ￥18,433
￥32,295 total
includes taxes & fees
Apr 24 - Apr 25
Lovely 2nd Floor Apartment
Apartment | Living area

Newly Renovated 2 floor Getaway

Newly Renovated 2 floor Getaway
3.5 star property
Forest Park
The price is ￥74,524
￥108,460 total
includes taxes & fees
Apr 26 - Apr 27
Newly Renovated 2 floor Getaway
1 bedroom, desk, iron/ironing board, travel crib

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, (75 reviews)
"An amazing location with the most friendly host! My mom, dog and i absolutely enjoyed this spot. Perfect for a fall get away and would stay again."
United States
Kelly Z.
The price is ￥28,694
￥44,694 total
includes taxes & fees
Apr 23 - Apr 24
The Creation Station is a cozy place so make yourself at home.
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
United States
Tom S.
The price is ￥63,508
￥111,550 total
includes taxes & fees
Apr 29 - Apr 30
Guesthouse Cabin vacation rentals in Berkshire County
Smart TV

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Amherst
9.8 out of 10, Exceptional, (111 reviews)
"Lovely place to stay and close to a nice cafe/market. Hosts were friendly and had fresh breakfast food in the refrigerator waiting for us. "
United States
Bill K.
The price is ￥20,719
￥30,237 total
includes taxes & fees
Apr 29 - Apr 30
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Fridge, microwave, oven, stovetop

Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (17 reviews)
"The house was lovely and clean and the location was very convenient for us. We would stay there again!"
United States
Jennifer S.
The price is ￥26,038
￥58,348 total
includes taxes & fees
Apr 28 - Apr 29
Cozy Home in Holyoke with 3 bedrooms
3 bedrooms, desk, iron/ironing board, travel crib

Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (12 reviews)
"The townhouse was perfect for our short trip. It was located close to everything we needed. The house was as described and we would stay here again."
United States
Matt G.
The price is ￥28,579
￥65,026 total
includes taxes & fees
Apr 28 - Apr 29
Townhouse with Pool Table - Renovated w/ King Bed
Exterior

Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (46 reviews)
"The creek, fire pit, wood stove, and cozy vibes were just great! "
United States
Jennifer F.
The price is ￥63,764
￥95,976 total
includes taxes & fees
Apr 26 - Apr 27
Bear Creek Cabin
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (144 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is ￥31,754
￥57,730 total
includes taxes & fees
Apr 30 - May 1
Big farmhouse in the foothills of the Berkshires
Fridge, microwave, oven, stovetop

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, (13 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 ￥91,103
￥116,561 total
includes taxes & fees
Apr 23 - Apr 24
Charming 3 bed/2 bath town home with gorgeous back yard
Exterior detail

comfort, luxury, privacy

comfort, luxury, privacy
Amherst
9.8 out of 10, Exceptional, (76 reviews)
"Great stay!"
United States
Shawn L.
The price is ￥19,368
￥28,757 total
includes taxes & fees
Apr 23 - Apr 24
comfort, luxury, privacy
Interior

Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (3 reviews)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
United States
AMY
The price is ￥55,634
￥100,782 total
includes taxes & fees
May 7 - May 8
Button's Modern Luxury Walkup Downtown Northampton
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (29 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is ￥32,281
￥49,768 total
includes taxes & fees
Apr 27 - Apr 28
Home in Great Barrington
Property grounds

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is ￥26,398
￥67,593 total
includes taxes & fees
Apr 23 - Apr 24
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (36 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is ￥57,228
￥115,739 total
includes taxes & fees
Apr 24 - Apr 25
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
House (4 Bedrooms) | Interior

12-acre Vacation Rental in the Berkshires!

12-acre Vacation Rental in the Berkshires!
3.0 star property
Charlemont
The price is ￥38,737
￥86,807 total
includes taxes & fees
Apr 23 - Apr 24
12-acre Vacation Rental in the Berkshires!
Interior

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!

Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Forest Park
9.2 out of 10, Wonderful, (29 reviews)
"Great. Placeto stay"
United States
Anonymous traveler
The price is ￥48,636
￥86,647 total
includes taxes & fees
May 4 - May 5
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
Smart TV, books

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, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is ￥25,537
￥62,890 total
includes taxes & fees
Apr 28 - Apr 29
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Fridge, microwave, oven, stovetop

Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
9.8 out of 10, Exceptional, (48 reviews)
"Our crew stayed here while working on a job in the area, they absolutely loved it, cleanliness was outstanding! Host provided great information about the area which was very helpful. Amenities are great! Would recommend 100% "
United States
Maureen A.
The price is ￥43,838
￥101,316 total
includes taxes & fees
Apr 26 - Apr 27
Spacious 5BR w/ Hot Tub & Games
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
"It was a very nice hotel."
Benjamin 1-night trip
Posted 1 hour ago
D. Hotel Suites & Spa

Find out more about Western Massachusetts

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