Vacation Homes in Hampshire County

Compare and save

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Top Cities in Hampshire County

Vacation Homes in Hampshire County

Our top choices for Hampshire County vacation homes

Peace and quiet on the lake

9.6 out of 10, Exceptional, (217)
"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "
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, (71)
"Great location for access to both Tanglewood and Lenox center. "
Enjoy comfortable elegance in this secluded grand home located in town

Poolside Luxe at Long Pond

9.0 out of 10, Wonderful, (2)
"Clean, pool has different depths which was a nice surprise, modern decoration, very well stocked"
Poolside Luxe at Long Pond

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

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

9.8 out of 10, Exceptional, (111)
"The weather didn’t cooperate enough for us to enjoy the water, but it was lovely to look at"
Enjoy the Fun of a Lakefront GetAway, While Only Minutes from Local Attractions!

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is SAR 604
SAR 1,781 total
includes taxes & fees
29 Sep - 30 Sep
Comfortable Berkshires retreat on mtn resort, SISO

Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

9.6 out of 10, Exceptional, (8)
"The house was clean, nicely decorated, comfortable and all the amenities we needed! "
Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

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

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!

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (34)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
The price is SAR 436
SAR 755 total
includes taxes & fees
10 Sep - 11 Sep
Lovely 2nd Floor Apartment

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

9.8 out of 10, Exceptional, (23)
"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

The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

10.0 out of 10, Exceptional, (1)
"Smooth and straightforward check-in process. They were accommodating to our schedule and communicated everything in a timely manner. House was clean and everything looked as listed. Kitchen was well stocked with up to date appliances and plenty of utensils which was a nice surprise. Plenty of space for 7 of us, would suggest bringing an air mattress though if with a larger party. Overwhelming positive experience overall. "
The price is SAR 1,021
SAR 1,853 total
includes taxes & fees
29 Sep - 30 Sep
The Olde Tobacco Barn - East Granby close to airport, restaurants & things to do

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

Newly Renovated 4 Bedroom House

10.0 out of 10, Exceptional, (2)
"The house was perfect for a weekend wedding trip. "
Newly Renovated 4 Bedroom House

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

Tiny Home with AC and WiFi in lovely Ludlow

8.8 out of 10, Excellent, (5)
The price is SAR 296
SAR 562 total
includes taxes & fees
2 Sep - 3 Sep
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. "
PICON COZY
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Hampshire County Hotel Reviews