Search Vacation Homes in The Berkshires

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
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Vacation Homes in The Berkshires

Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
10.0 out of 10, Exceptional, (3)
"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
28 Oct - 29 Oct
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Property grounds
Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (39)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 724
AED 1,658 total
includes taxes & fees
11 Nov - 12 Nov
Cheerful 3-bedroom cottage with woodstove
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISO
8.8 out of 10, Excellent, (6)
"Kind and responsive host."
United States
Javier
The price is AED 591
AED 1,792 total
includes taxes & fees
26 Oct - 27 Oct
Comfortable Berkshires retreat on mtn resort, SISO
Smart TV, books
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
9.6 out of 10, Exceptional, (8)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is AED 588
AED 1,441 total
includes taxes & fees
27 Oct - 28 Oct
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Exterior
North Getaway Cottage
North Getaway Cottage
9.2 out of 10, Wonderful, (22)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
United States
Caroline J.
The price is AED 744
AED 1,614 total
includes taxes & fees
27 Oct - 28 Oct
North Getaway Cottage
Fridge, microwave, oven, stovetop
Home in Great Barrington
Home in Great Barrington
9.8 out of 10, Exceptional, (24)
"Crisp and clean with a great location.Wonderful choice."
United States
Richard B.
The price is AED 698
AED 1,120 total
includes taxes & fees
23 Nov - 24 Nov
Home in Great Barrington
Smart TV, fireplace, books
Cozy. Clean. Free bagel shop.
Cozy. Clean. Free bagel shop.
10.0 out of 10, Exceptional, (10)
"The perfect location for a stay in Great Barrington. The house is so well done and very comfortable!"
United States
Carly F.
The price is AED 1,322
AED 2,232 total
includes taxes & fees
4 Nov - 5 Nov
Cozy. Clean. Free bagel shop.
Exterior
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
9.8 out of 10, Exceptional, (72)
"We had a wonderful stay, thank you! "
United States
Gary L.
The price is AED 988
AED 2,051 total
includes taxes & fees
26 Oct - 27 Oct
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Fridge, microwave, oven, stovetop
Great Barrington Get Away
Great Barrington Get Away
9.4 out of 10, Exceptional, (24)
"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "
United States
Amy B.
The price is AED 937
AED 1,764 total
includes taxes & fees
27 Oct - 28 Oct
Great Barrington Get Away
Fridge, microwave, oven, stovetop
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Sun Filled Lenox Retreat - Minutes to Tanglewood!
9.4 out of 10, Exceptional, (3)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is AED 698
AED 1,719 total
includes taxes & fees
30 Oct - 31 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Game room
Pet Friendly Riverfront Home in Great Barrington
Pet Friendly Riverfront Home in Great Barrington
9.0 out of 10, Wonderful, (2)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AED 744
AED 950 total
includes taxes & fees
29 Oct - 30 Oct
Pet Friendly Riverfront Home in Great Barrington
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Cozy. Clean. Free bagel shop. 3 Fireplaces.
The price is AED 1,249
AED 2,158 total
includes taxes & fees
5 Nov - 6 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Exterior
Bungalow in the Berkshires
Bungalow in the Berkshires
10.0 out of 10, Exceptional, (3)
"We had a lovely stay. Easy check in and communication was great. "
United States
Dale G.
The price is AED 1,102
AED 1,534 total
includes taxes & fees
26 Oct - 27 Oct
Bungalow in the Berkshires
Fridge, microwave, oven, stovetop
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is AED 988
AED 1,806 total
includes taxes & fees
26 Oct - 27 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Exterior
Spacious 6BR Near Jiminy Peak – Hot Tub, Game Room & Ski Lift Ticket Discount
Spacious 6BR Near Jiminy Peak – Hot Tub, Game Room & Ski Lift Ticket Discount
10.0 out of 10, Exceptional, (15)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AED 2,200
AED 4,081 total
includes taxes & fees
28 Oct - 29 Oct
Spacious 6BR Near Jiminy Peak – Hot Tub, Game Room & Ski Lift Ticket Discount
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi
Spacious 5-bedroom house in charming Lee with WiFi
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is AED 1,322
AED 2,626 total
includes taxes & fees
30 Oct - 31 Oct
Spacious 5-bedroom house in charming Lee with WiFi
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (1)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is AED 2,311
AED 5,174 total
includes taxes & fees
25 Oct - 26 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Property grounds
The Creation Station is a cozy place so make yourself at home.
The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (70)
"This was our second time staying here and we had a great time!"
United States
Andy L.
The price is AED 661
AED 1,026 total
includes taxes & fees
29 Oct - 30 Oct
The Creation Station is a cozy place so make yourself at home.
Fridge, microwave, oven, stovetop
Linny's Lakeview Cottage - Cozy, fun & updated
Linny's Lakeview Cottage - Cozy, fun & updated
10.0 out of 10, Exceptional, (63)
"Very great location, close to my family. Great spot!!"
United States
Craig M.
Linny's Lakeview Cottage - Cozy, fun & updated
Interior
Lovely 2nd Floor Apartment
Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (41)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
United States
Shanyn
The price is AED 426
AED 747 total
includes taxes & fees
27 Oct - 28 Oct
Lovely 2nd Floor Apartment
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top The Berkshires Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"We loved this place. Quiet, very clean,attractive. Loved that it had a kitchen area. Second story, sliding glass doors overlooked the fall foliage in the back of the building. Very peaceful.."
Steven 4-night trip
Posted 2 days ago
Berkshire Mountain Lodge

Explore a world of travel with Expedia