Vacation Homes in Hampshire County

Compare and save

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

Vacation Home in Colrain

9.8 out of 10, Exceptional, (38)
"Great place and convenient to get to and from Berkshire East."
United States
Jeffrey B.
The price is AED 1,010
AED 2,326 total
includes taxes & fees
1 Dec - 2 Dec
FaLL Western Mass Getaway-Airhockey-Firepit

Vacation Home in Great Barrington

9.4 out of 10, Exceptional, (6)
The price is AED 744
AED 1,093 total
includes taxes & fees
1 Dec - 2 Dec
Pet Friendly Riverfront Home in Great Barrington

Vacation Home in Ludlow

8.4 out of 10, Very Good, (8)
"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."
United States
Matthew H.
The price is AED 290
AED 550 total
includes taxes & fees
1 Dec - 2 Dec
Tiny Home with AC and WiFi in lovely Ludlow

Vacation Home in Stockbridge

10.0 out of 10, Exceptional, (134)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Vacation Home in Goshen

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had such a great time staying here as always. "
United States
David F.
Experience Three Sisters Sanctuary in Goshen, MA

Vacation Home in Lanesborough

10.0 out of 10, Exceptional, (6)
"Everything was just as advertised and we really enjoyed the view and the hot tub. Perfect spot for a quick getaway! "
United States
Cindy B.
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Vacation Home in Sherwood Forest

9.6 out of 10, Exceptional, (230)
"This property provides direct access to a lovely lake for kayaking and swimming. It is also a terrific location for Berkshire musts such as Jacob's Pillow and Tanglewood. The owner is quickly responsive to questions and directions for check in were easy to follow. The house has strong WiFi for any work days you have while traveling. Highly recommend and look forward to staying there again in the future! "
United States
Leslie K.
Peace and quiet on the lake

Vacation Home in Pittsfield

9.8 out of 10, Exceptional, (149)
"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."
United States
Sarah A.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Vacation Home in Lanesborough

9.6 out of 10, Exceptional, (74)
"Beautiful house and location that was perfect for a family weekend. Would 100% recommend!"
United States
Shaun L.
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

Vacation Home in Lee

9.6 out of 10, Exceptional, (18)
"Great communication, perfect location for everything we wanted to do that weekend and a beautiful home! We used the indoor and outdoor spaces and had a wonderful time!"
United States
Julie L.
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Vacation Home in South End

2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautifully renovated and easy travels to many family and adult attractions locally. Parking is street side and we never had an issue parking our 2 vehicles out front of the home."
United States
Molly S.
Updated 3Bedroom. 5beds group ready.Walk to the Casino and play game of Pool.

Vacation Home in Charlemont

The price is AED 588
AED 1,518 total
includes taxes & fees
1 Dec - 2 Dec
Riverbend Berkshire East Basecamp - 3 bedrooms available

Vacation Home in Shelburne Falls

2.0 star property
10.0 out of 10, Exceptional, (19)
"Great place to stay ,close to town.Very clean."
United States
Hope D.
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

Vacation Home in Lee

10.0 out of 10, Exceptional, (21)
"Wonderful stay, beautiful, well equipped and clean property. Highly recommend for an adult famiky getaway "
United States
jennifer r.
Berkshire House Stay

Vacation Home in Forest Park

9.8 out of 10, Exceptional, (36)
"Amazing stay! Conscientious to Tanglewood, and the property is fabulous. Highly recommend!"
United States
Maria E.
The price is AED 866
AED 1,391 total
includes taxes & fees
28 Dec - 29 Dec
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Vacation Home in Lenox

9.2 out of 10, Wonderful, (33)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
United States
Jacquie S.
Amore Estate - beautiful room with many places to explore and relax in.

Vacation Home in Whitingham

10.0 out of 10, Exceptional, (50)
"Great stay perfect for 2 people, relax on then porch and look at the lake! "
United States
Keith D.
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Vacation Home in Pine Point

2.0 star property
9.6 out of 10, Exceptional, (7)
"The whole experience was great. The host was very nice and the place is comfy and enjoyable to stay at. Highly recommend. "
United States
Joel K.
3-bedroom house in perfect Springfield with WiFi, AC

Vacation Home in Sherwood Forest

10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 536
AED 1,386 total
includes taxes & fees
1 Dec - 2 Dec
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Stockbridge

10.0 out of 10, Exceptional, (103)
"Great house with gracious and responsive hosts. Everything in working order and the houseclean and grand."
United States
David H.
A Grand property in Historic Stockbridge
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.

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels
Save an average of 15% on thousands of hotels when you're signed in

Top Hampshire County Hotel Reviews