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Browse Select Western Massachusetts Holiday Homes

Our top choices for Western Massachusetts holiday homes

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (146)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (5)
Contemporary Berkshire Home with Views of Taconic Golf Course

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (70)
"Great location for access to both Tanglewood and Lenox center. "
Enjoy comfortable elegance in this secluded grand home located in town

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (48)
"What a wonderful property for our girls trip! The house is clean, there’s so much hangout space, and it’s so well supplied. "
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (128)
"Fantastic home! Clean, well stocked and very comfortable. We had a great time and will be back. The owner was kind, considerate and appreciative of our stay. Thanks again! "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Poolside Luxe at Long Pond

10.0 out of 10, Exceptional, (1)
"Clean, pool has different depths which was a nice surprise, modern decoration, very well stocked"
Poolside Luxe at Long Pond

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is £367
includes taxes & fees
26 Aug - 27 Aug
Comfortable Berkshires retreat on mtn resort, SISO

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (37)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Linny’s Lake Retreat, Family-Friendly & Dock Access

9.8 out of 10, Exceptional, (22)
"Amazing place and great hosts! This place was perfect for us to stay while in town visiting family. Will definitely be staying here again"
Linny’s Lake Retreat, Family-Friendly & Dock Access

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (54)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (33)
"Easy stay, good location for us. Would stay again. "
The price is £152
includes taxes & fees
27 Aug - 28 Aug
Lovely 2nd Floor Apartment

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

9.8 out of 10, Exceptional, (107)
"My wife and I stayed in the upper apartment for 2 nights. The place was perfect in every aspect. It was clean, quiet and well equipped. Beds were comfortable and it was close the UMASS. We will definitely stay here again when we are in the area. "
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

Old World Charm, Modern Conveniences - 3 BR private home in quiet setting

10.0 out of 10, Exceptional, (20)
"This beautiful home was perfect for our short stay in Western Massachusetts. Everything was just lovely, clean, comfortable, quiet. Great hosts and so kind and accommodating to our needs. Thank you so much. We will definitely look to stay here again for future family visits. "
Old World Charm, Modern Conveniences - 3 BR private home in quiet setting

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"We thoroughly enjoyed our stay and would go again. The host was easy to communicate with and answered our questions quickly. Hope we get to take advantage of the pretty backyard next time. "
The price is £379
includes taxes & fees
3 Sept - 4 Sept
Cheerful 3-bedroom cottage with woodstove

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

10.0 out of 10, Exceptional, (27)
"Spacious, welcoming, so well stocked, we felt lucky to find the property."
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Tiny Home with AC and WiFi in lovely Ludlow

8.6 out of 10, Excellent, (4)
"Good stay for an overnight in the area, location was a little tricky to find at night but once I did it was easy to get in. Had all the amenities needed for a short stay and is near the highway for quick on and off."
The price is £114
includes taxes & fees
25 Aug - 26 Aug
Tiny Home with AC and WiFi in lovely Ludlow

PICON COZY

7.4 out of 10, Good, (69)
"This home has the basics and is reasonably comfortable. The parking is good and the area is walkable. It was adequate for my needs. "
The price is £126
includes taxes & fees
25 Aug - 26 Aug
PICON COZY

Lakefront Bungalow

9.6 out of 10, Exceptional, (10)
"Nice location on water, clean, kitchen had all our needs--would stay there again."
Lakefront Bungalow

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (47)
"We went as a family to get away from the city life for the weekend. We have no complaints except that it could’ve been a bit cleaner in the sense that there were many cobwebs. Nonetheless we rlly enjoyed our weekend in Great Barrington "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
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