Western Massachusetts Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Western Massachusetts holiday rentals

Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,350 reviews)
"great stay. "
United States
John
The price is HK$676
HK$841 total
includes taxes & fees
17 May - 18 May
Vacation Village in the Berkshires
Living area

Newly Renovated 2 floor Getaway

Newly Renovated 2 floor Getaway
3.5 star property
Forest Park
The price is HK$3,662
HK$5,329 total
includes taxes & fees
11 May - 12 May
Newly Renovated 2 floor Getaway
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 HK$1,332
HK$2,966 total
includes taxes & fees
19 May - 20 May
Cozy Home in Holyoke with 3 bedrooms
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 HK$909
HK$1,585 total
includes taxes & fees
20 May - 21 May
Lovely 2nd Floor Apartment
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 traveller
The price is HK$2,383
HK$4,285 total
includes taxes & fees
19 May - 20 May
Kid friendly neighborhood! Everyone is welcomed in this cozy apartment home!
1 bedroom, desk, iron/ironing board, travel cot

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 HK$1,410
HK$2,152 total
includes taxes & fees
11 May - 12 May
The Creation Station is a cozy place so make yourself at home.
3 bedrooms, desk, iron/ironing board, travel cot

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 house was clean, comfortable and had everything covered for the weekend. A must stay when traveling to Chicopee."
United States
RAFAEL U.
The price is HK$1,607
HK$3,485 total
includes taxes & fees
19 May - 20 May
Townhouse with Pool Table - Renovated w/ King Bed
Interior

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
2.5 star property
Holyoke
The price is HK$540
HK$1,861 total
includes taxes & fees
11 May - 12 May
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
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 HK$980
HK$1,444 total
includes taxes & fees
12 May - 13 May
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
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, (37 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is HK$2,812
HK$5,643 total
includes taxes & fees
11 May - 12 May
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
TV, fireplace, printers

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, (4 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 HK$4,435
HK$10,407 total
includes taxes & fees
10 May - 11 May
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Property grounds

Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (8 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is HK$3,916
HK$4,978 total
includes taxes & fees
11 May - 12 May
Cozy Valley View Post & Beam Villa!
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 HK$3,133
HK$4,681 total
includes taxes & fees
13 May - 14 May
Bear Creek Cabin
Living area

Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield

Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
Sixteen Acres
8.8 out of 10, Excellent, (5 reviews)
"Great place to stay. It was clean and organized. Our family enjoyed this location, what it had to provide, and the host was great. "
United States
Diana P.
The price is HK$1,621
HK$2,844 total
includes taxes & fees
19 May - 20 May
Charming -Clean-4-bedroom house with AC and WiFi in wonderful Springfield
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 family and friends loved everything about this home. It is better than pictures and so convenient to mountain. Easy check-in and great communication with Erika and Casey. We will definitely be back and try some warm weather adventures. "
United States
Brandy G.
The price is HK$2,131
HK$4,892 total
includes taxes & fees
10 May - 11 May
Spacious 5BR w/ Hot Tub & Games
Dining

Charlemont Chalet - A 15 Acre Private Retreat

Charlemont Chalet - A 15 Acre Private Retreat
Charlemont
The price is HK$2,878
HK$5,393 total
includes taxes & fees
20 May - 21 May
Charlemont Chalet - A 15 Acre Private Retreat
Exterior detail

comfort, luxury, privacy

comfort, luxury, privacy
Amherst
9.8 out of 10, Exceptional, (78 reviews)
"Great stay!"
United States
Shawn L.
The price is HK$952
HK$1,413 total
includes taxes & fees
11 May - 12 May
comfort, luxury, privacy
Fridge, microwave, oven, stovetop

Historic downtown house. Unscented products and sustainability practices.

Historic downtown house. Unscented products and sustainability practices.
Northampton
10.0 out of 10, Exceptional, (7 reviews)
"The house was very comfortable and we enjoyed our visit very much "
United States
Debbie L.
The price is HK$3,290
HK$5,827 total
includes taxes & fees
19 May - 20 May
Historic downtown house. Unscented products and sustainability practices.
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Great location and nice size house for a family of 5. We had a couple hiccups but the host responded quickly and handled things promptly. "
United States
Jennifer L.
The price is HK$1,586
HK$2,480 total
includes taxes & fees
10 May - 11 May
Cozy Riverside Berkshires Retreat
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,856
HK$3,937 total
includes taxes & fees
10 May - 11 May
Cheerful 3-bedroom cottage with woodstove
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

Hampton Inn & Suites Springfield/Downtown

Hampton Inn & Suites Springfield/Downtown

10/10 Excellent
"Spacious, clean room. Front desk staff was very friendly at both check in and check out. Decent breakfast with a good variety"
Robert 1-night trip
Posted 12 hours ago
Hampton Inn & Suites Springfield/Downtown

Find out more about Western Massachusetts

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