Holiday Homes in The Berkshires

    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

Featured Holiday Homes in The Berkshires and around

Our top choices for The Berkshires holiday homes

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (256)
"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 €200
includes taxes & fees
16 Sept - 17 Sept
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 €435
includes taxes & fees
11 Sept - 12 Sept
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

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

9.6 out of 10, Exceptional, (8)
"My boyfriend and I loved our stay at the cottage. Nicole was very easy to communicate with. The house was cozy and had everything we needed. Even though it rained all weekend, the hot tub and games made up for it. Thank you, Nicole! Can't wait to come back!"
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

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 €343
includes taxes & fees
3 Sept - 4 Sept
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

North Getaway Cottage

9.6 out of 10, Exceptional, (21)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is €387
includes taxes & fees
4 Sept - 5 Sept
North Getaway Cottage

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is €420
includes taxes & fees
1 Sept - 2 Sept
Comfortable Berkshires retreat on mtn resort, SISO

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (3)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
The price is €436
includes taxes & fees
1 Oct - 2 Oct
NEW RENO Historic Creamery in Berkshires w/hot tub

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"We thoroughly enjoyed our stay and would go again. The host was easy to communicate with and answered our questions quickly. Hope we get to take advantage of the pretty backyard next time. "
The price is €441
includes taxes & fees
9 Sept - 10 Sept
Cheerful 3-bedroom cottage with woodstove

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (2)
"Great location, very clean and well appointed with everyth"
Bungalow in the Berkshires

Sun Filled Lenox Retreat - Minutes to Tanglewood!

10.0 out of 10, Exceptional, (1)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
The price is €447
includes taxes & fees
1 Sept - 2 Sept
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
The price is €920
includes taxes & fees
3 Sept - 4 Sept
Hancock Village Inn at Jiminy Peak

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!

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 €499
includes taxes & fees
14 Sept - 15 Sept
Great Barrington Get Away

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

Spacious 5-bedroom house in charming Lee with WiFi

The price is €756
includes taxes & fees
6 Sept - 7 Sept
Spacious 5-bedroom house in charming Lee with WiFi

Cozy Carriage House room with a double bed and private balcony

The price is €302
includes taxes & fees
1 Sept - 2 Sept
Cozy Carriage House room with a double bed and private balcony

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

The price is €395
includes taxes & fees
4 Sept - 5 Sept
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Experience Timeless Elegance in The Edith Wharton Room!

The price is €266
includes taxes & fees
1 Sept - 2 Sept
Experience Timeless Elegance in The Edith Wharton Room!
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

Find out more about The Berkshires

Find out more about The Berkshires

The Berkshires Holiday Homes information

Number of reviews
Accommodation
355 Holiday Homes
Lowest Price
€420
Highest Price
€441

Explore a world of travel with Expedia

Explore a world of travel with Expedia