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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Sep - 21 Sep
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Vacation Homes in The Berkshires

Our top choices for The Berkshires vacation homes

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

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 AED 551
AED 837 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!
Fridge, microwave, oven, stovetop

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 AED 988
AED 1,822 total
includes taxes & fees
11 Sep - 12 Sep
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Smart TV, books

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 AED 654
AED 1,526 total
includes taxes & fees
22 Sep - 23 Sep
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Home in Great Barrington
Fridge, microwave, oven, stovetop

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Enjoyed our stay!!!"
The price is AED 612
AED 1,015 total
includes taxes & fees
10 Sep - 11 Sep
Home in Great Barrington
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Outdoor dining

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 AED 595
AED 1,456 total
includes taxes & fees
4 Sep - 5 Sep
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
North Getaway Cottage
Exterior

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."
North Getaway Cottage
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
1 bedroom, bed sheets

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

The price is AED 1,320
AED 1,803 total
includes taxes & fees
7 Sep - 8 Sep
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
NEW RENO Historic Creamery in Berkshires w/hot tub
Terrace/patio

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 AED 749
AED 1,735 total
includes taxes & fees
4 Sep - 5 Sep
NEW RENO Historic Creamery in Berkshires w/hot tub
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is AED 591
AED 1,743 total
includes taxes & fees
4 Sep - 5 Sep
Comfortable Berkshires retreat on mtn resort, SISO
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Microwave, oven, stovetop, dishwasher

Cozy. Clean. Free bagel shop. 3 Fireplaces.

The price is AED 1,322
AED 2,215 total
includes taxes & fees
4 Sep - 5 Sep
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Cheerful 3-bedroom cottage with woodstove
Property grounds

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. "
Cheerful 3-bedroom cottage with woodstove
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
The price is AED 2,384
AED 4,315 total
includes taxes & fees
2 Oct - 3 Oct
Hancock Village Inn at Jiminy Peak
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, oven, stovetop

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 AED 837
AED 1,867 total
includes taxes & fees
4 Sep - 5 Sep
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Bungalow in the Berkshires
Exterior

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (2)
"Great location, very clean and well appointed with everyth"
The price is AED 1,377
AED 1,854 total
includes taxes & fees
4 Sep - 5 Sep
Bungalow in the Berkshires
3-bedroom house in beautiful Berkshires, close to amenities!
Property grounds

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

The price is AED 738
AED 1,201 total
includes taxes & fees
22 Sep - 23 Sep
3-bedroom house in beautiful Berkshires, close to amenities!
Great Barrington Get Away
Fridge, microwave, oven, stovetop

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 AED 1,194
AED 2,097 total
includes taxes & fees
9 Sep - 10 Sep
Great Barrington Get Away
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Exterior

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
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is AED 1,194
AED 2,462 total
includes taxes & fees
1 Oct - 2 Oct
Spacious 5-bedroom house in charming Lee with WiFi
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

The price is AED 762
AED 1,118 total
includes taxes & fees
4 Sep - 5 Sep
Experience Timeless Elegance in The Edith Wharton Room!
Cozy Carriage House room with a double bed and private balcony
1 bedroom, bed sheets

Cozy Carriage House room with a double bed and private balcony

The price is AED 879
AED 1,265 total
includes taxes & fees
4 Sep - 5 Sep
Cozy Carriage House room with a double bed and private balcony
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
Sign in
Sign up, it's free

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Room was very clean. There is a lot to do at the property, 2 pools, activities for the kids. Lots of things to do in the area "
Judy 2-night trip
Posted 6 days ago
Vacation Village in the Berkshires
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

10/10 Excellent
"Fantastic breakfast, perfect location, fun vibe, beautiful pool area, an environment that encourages conversation with other guests. Room was spacious but needed a nightstand on either side of the bed. "
Leigh 1-night trip
Posted 13 days ago
The Porches Inn at Mass MoCA

Explore a world of travel with Expedia

Explore a world of travel with Expedia