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Compare 465 Vacation Homes in Western Massachusetts with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (245)
"What a great spot to stay for the few days we were there Can’t wait to come back! "
The price is AED 551
AED 841 total
includes taxes & fees
10 May - 11 May
Berkshire Village Carriage House - Super Private!!

Author Stephen Oates Once Owned

8.0 out of 10, Very Good, (2)
"The house is very close to Amherst on a quiet street. Plenty of room, comfortable beds, and well supplied. We’d stay again! "
The price is AED 1,466
AED 2,261 total
includes taxes & fees
12 May - 13 May
Author Stephen Oates Once Owned

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is AED 2,016
AED 3,810 total
includes taxes & fees
12 May - 13 May
Hancock Village Inn at Jiminy Peak

PICON COZY

7.6 out of 10, Good, (65)
"Picon Cozy was a great place to rest our weary heads. The neighborhood was quiet and the lodging/amenities met our needs very nicely. We'll definitely consider this place for future visits to the Springfield area 😊."
The price is AED 275
AED 625 total
includes taxes & fees
15 May - 16 May
PICON COZY

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

10.0 out of 10, Exceptional, (151)
"Hi,The views are spectacular, house is spacious and close to skiing. We had a great time staying in this house. We even talked about coming back in warmer weather. "
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

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

9.8 out of 10, Exceptional, (98)
"We were attending a horse show locally. We stayed a few nights and everything about this day was easy from start to finish."
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (73)
"Very spacious and comfortable. Biggest selling point was its proximity to family in the area."
1810 Brook Side Mill/House / EV Level 2 Charging on Site

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.

Peace and quiet on the lake

9.6 out of 10, Exceptional, (214)
"We enjoyed the privacy and quiet of the location. The house itself is very well kept inside and cozy. "
Peace and quiet on the lake

Lakeside Oasis Just You, The Lake & The View!

9.8 out of 10, Exceptional, (70)
"Perfect location for a peaceful, scenic vacation."
Lakeside Oasis Just You, The Lake & The View!

Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

9.8 out of 10, Exceptional, (11)
"We had a great stay at Nick's place. place was very clean and spacious, good layout. Nick was easy to reach and communication was great. We would definitely book again! thank you! "
The price is AED 606
AED 1,052 total
includes taxes & fees
11 May - 12 May
Quiet 3 BR 1.5 Bath Duplex Near 5 Colleges, Connecticut River, and Hiking Trails

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (71)
"Going to the Berkshires this is a great place to stay. It is within walking distance to over 8 restaurants in downtown Lenox. Great gas stove and comfortable bed. Owner makes sure your stay is great. Would stay here again. "
Heart of Lenox Walk to Town Cozy Cottage!

Thomas's Cozy Duplex - Centrally Located

8.4 out of 10, Very Good, (11)
"Quiet and comfy "
Thomas's Cozy Duplex - Centrally Located

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"
The Race Mountain House

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (36)
"The property was centrally located for skiing, and was a comfortable stay."
The price is AED 687
AED 1,621 total
includes taxes & fees
13 May - 14 May
Cheerful 3-bedroom cottage with woodstove

Owl's Nest - Cozy Westfield Home w/ Fire Pit

9.0 out of 10, Wonderful, (4)
"Property worked well for us "
The price is AED 730
AED 1,882 total
includes taxes & fees
8 Jun - 9 Jun
Owl's Nest - Cozy Westfield Home w/ Fire Pit

Perfect Nature Haven In Great Barrington

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great time at the house. We had everything we needed. It was close to town. The space is very comfortable."
Perfect Nature Haven In Great Barrington

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (4)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Hilltown Nest is a wonderful place for family and friends to gather.

9.8 out of 10, Exceptional, (15)
"Sadly we were only here for a couple of nights, but this place was very nice. I manage vacation rentals myself and i was very impressed by the cleanliness of this place, especially considering the size of it. The house is great for a family with lots of room to spread out. Our grandkids enjoyed tinkling on the piano and playing in the backyard. Would definitely choose to stay here again!"
Hilltown Nest is a wonderful place for family and friends to gather.

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (5)
"Lovely ski weekend! Best memory: hot tubbing at sunset after skiing with snow falling all around! "
Mountain Blossom Retreat by Evergreen Home
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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Other property types in Western Massachusetts

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1804)
"The property was clean and the staff very accommodated."
The price is AED 403
AED 490 total
includes taxes & fees
11 May - 12 May
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (929)
"Out dated not many resort like options "
The price is AED 488
AED 545 total
includes taxes & fees
10 May - 11 May
Jiminy Peak Mountain Resort

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
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.