Search Vacation Homes in The Berkshires

Start date: Check-in selected.
End date: Check-out
    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

Next weekend
In two weeks
In one month
In two months

Vacation Homes in The Berkshires

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (259)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
The price is SAR 563
SAR 863 total
includes taxes & fees
16 Sep - 17 Sep
Berkshire Village Carriage House - Super Private!!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is SAR 1,010
SAR 1,815 total
includes taxes & fees
12 Sep - 13 Sep
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Enjoyed our stay!!!"
Home in Great Barrington

Experience Timeless Elegance in The Edith Wharton Room!

The price is SAR 778
SAR 1,142 total
includes taxes & fees
14 Sep - 15 Sep
Experience Timeless Elegance in The Edith Wharton Room!

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
11 Sep - 12 Sep
Comfortable Berkshires retreat on mtn resort, SISO

Cozy 2BR/1BA Furnished In-Apartment – Quiet Country

The price is SAR 396
SAR 1,204 total
includes taxes & fees
15 Sep - 16 Sep
Cozy 2BR/1BA Furnished In-Apartment – Quiet Country

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."
The price is SAR 889
SAR 1,852 total
includes taxes & fees
14 Sep - 15 Sep
Cheerful 3-bedroom cottage with woodstove

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (4)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
NEW RENO Historic Creamery in Berkshires w/hot tub

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."
The price is SAR 601
SAR 1,476 total
includes taxes & fees
22 Sep - 23 Sep
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Amazing Inn. Cozy and everything we needed. "
The price is SAR 2,248
SAR 4,169 total
includes taxes & fees
11 Sep - 12 Sep
Hancock Village Inn at Jiminy Peak

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

The price is SAR 1,347
SAR 3,517 total
includes taxes & fees
11 Sep - 12 Sep
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

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

9.8 out of 10, Exceptional, (71)
"We had a wonderful stay, thank you! "
The price is SAR 983
SAR 2,008 total
includes taxes & fees
14 Sep - 15 Sep
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

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."
The price is SAR 856
SAR 1,903 total
includes taxes & fees
14 Sep - 15 Sep
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"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. "
The price is SAR 1,126
SAR 2,020 total
includes taxes & fees
1 Oct - 2 Oct
Great Barrington Get Away

The Race Mountain House

2.0 star property
9.2 out of 10, Wonderful, (5)
"I spent my 60th birthday with a few friends at Mountain House and it was even better than I dreamed. The comfort and simplicity of the decor along with the mountain views. A must for those who like simple elegance."
The Race Mountain House

Spacious 5-bedroom house in charming Lee with WiFi

The price is SAR 1,098
SAR 2,307 total
includes taxes & fees
17 Sep - 18 Sep
Spacious 5-bedroom house in charming Lee with WiFi

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (2)
"Great location, very clean and well appointed with everyth"
The price is SAR 1,407
SAR 1,894 total
includes taxes & fees
11 Sep - 12 Sep
Bungalow in the Berkshires

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is SAR 608
SAR 1,488 total
includes taxes & fees
24 Sep - 25 Sep
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.
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 The Berkshires Hotel Reviews