Vacation Homes in Hampshire County

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Top Cities in Hampshire County

Compare 382 Vacation Homes in Hampshire County with updated reviews, rates, and availability.

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

10.0 out of 10, Exceptional, (63)
"It was an amazing stay. The host was very proactive and helpful. "
The price is AED 962
AED 1,969 total
includes taxes & fees
25 Nov - 26 Nov
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Historic Farmhouse Near Mountains & Colleges!

10.0 out of 10, Exceptional, (3)
"A group of us traveled quite a distance and were so happy to see the great place for us to stay. The house was beautifully restored and tastefully decorated. We felt at home immediately. There were enough room for all of us to spread out and do work or school studies without interrupting others and the back yard was big enough for the kids to blow off steam. The enclosed sunroom was the most popular room in the entire place. This place was top notch! Absolutely perfect!!"
Historic Farmhouse Near Mountains & Colleges!

Amore Estate - beautiful room with many places to explore and relax in.

9.8 out of 10, Exceptional, (17)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.

completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

10.0 out of 10, Exceptional, (180)
"Overall a wonderful stay. This is a duplex and the owner lives next door. Nice neighborhood and beautiful view"
completely renovated 3 bedroom, 2 bath overlooking idyllic lake whittemore

Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

9.8 out of 10, Exceptional, (102)
"Very nice, well equipped, absolutely beautiful view!!!!!!"
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

Secluded Family Home in Serene Stockbridge Woods

10.0 out of 10, Exceptional, (18)
"We spent a short weekend here in Stockbridge to attend the Naumkeag Pumpkin Show. The kids (2 + 4) were in amazement the entire time. The house was a fantastically creative environment with books, games, toys, and a massive yard with swings. A+ would stay again."
Secluded Family Home in Serene Stockbridge Woods

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.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is AED 525
AED 812 total
includes taxes & fees
25 Nov - 26 Nov
Berkshire Village Carriage House - Super Private!!

PICON COZY

7.6 out of 10, Good, (54)
"I booked this for my daughter who is looking to relocate to Western Mass from Central Mass and it was perfect for her. The host was extra helpful and accomodating, and while it was a small and simple space, she was very comfortable and cozy. She would definitely stay again."
The price is AED 275
AED 625 total
includes taxes & fees
2 Dec - 3 Dec
PICON COZY

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

9.6 out of 10, Exceptional, (40)
"This property is stunning. It fit our group of 14 perfectly. There are so many unique details and beautiful furniture. The kitchen was well-stocked for pots/pans/utensils/cleaning supplies which I always appreciate - makes group meals so much easier to manage. Quiet area, would be great all year round depending on what activities you like. Hot tub was a major highlight!"
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

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

10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Large relaxing house in 25 acres of private woods with lake access.

10.0 out of 10, Exceptional, (16)
"Excellent home in the woods. All as advertised, my family and I thoroughly enjoyed it. Communication with the owner was excellent. 10/10, we’ll be back next time we’re in the area"
Large relaxing house in 25 acres of private woods with lake access.

Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

10.0 out of 10, Exceptional, (105)
"We really enjoyed our stay at Julie’s home. We will definitely to look to stay here again the next time we visit the area. Highly recommended! "
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Lovely 3-bedroom City Escape

9.8 out of 10, Exceptional, (17)
"A couple friends and I stayed for a long weekend to play local disc golf and thoroughly enjoyed our stay. We loved how spacious, comfortable, and clean Christopher's place was and were thankful to each have our own bedroom. Will definitely be back!"
Lovely 3-bedroom City Escape

Charming 4Bds+1crib house with patio Amherst Center

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great location near restaurants and stores. House is "
The price is AED 676
AED 1,432 total
includes taxes & fees
19 Dec - 20 Dec
Charming 4Bds+1crib house with patio Amherst Center

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

9.6 out of 10, Exceptional, (29)
"It was nice stay!"
The price is AED 687
AED 1,171 total
includes taxes & fees
6 Dec - 7 Dec
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

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

10.0 out of 10, Exceptional, (146)
"Beautiful fall colors surrounding the lake. "
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

Tranquil 3-BR Waterfront Retreat

9.8 out of 10, Exceptional, (10)
"Very clean and nicely decorated. Comfortable vibe. Came to relax and enjoy the fall colors. It looks bigger in the pictures, but was plenty big for the 4 of us. Having laundry was a plus, and enjoyed the ping pong table Loved the duvet covers…so soft. Upstairs bathroom could use a mirror in a better place, as blow drying hair and putting on makeup would be difficult, but just didn’t bother. Hope to go again next fall. "
Tranquil 3-BR Waterfront Retreat

The Creation Station is a cozy place so make yourself at home.

10.0 out of 10, Exceptional, (61)
"We needed a pet friendly location to stay for one night. This place is amazing. Very unconventional and much more than I needed for my family of four but I would recommend it highly. The host was very helpful and friendly. The property would be great for an adult birthday or an extended family get together. "
The price is AED 661
AED 1,034 total
includes taxes & fees
26 Nov - 27 Nov
The Creation Station is a cozy place so make yourself at home.

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (14)
"The house was perfect for us as we moved our daughter into UMASS. Close to the college, restaurants and shopping. Very clean house and had everything we needed. "
Amherst, Perfect Location, UMass, Smith, MHC!
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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