Holiday Homes in The Berkshires

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Holiday Homes in The Berkshires

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

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (255)
"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 AU$347
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!
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 AU$818
includes taxes & fees
11 Sept - 12 Sept
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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 AU$759
includes taxes & fees
20 Aug - 21 Aug
Comfortable Berkshires retreat on mtn resort, SISO
North Getaway Cottage
Exterior

North Getaway Cottage

9.6 out of 10, Exceptional, (20)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is AU$694
includes taxes & fees
20 Aug - 21 Aug
North Getaway Cottage
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 AU$807
includes taxes & fees
1 Sept - 2 Sept
Sun Filled Lenox Retreat - Minutes to Tanglewood!
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 AU$748
includes taxes & fees
20 Aug - 21 Aug
NEW RENO Historic Creamery in Berkshires w/hot tub
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, WiFi, bed sheets

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

The price is AU$499
includes taxes & fees
3 Sept - 4 Sept
Elegant Carriage House room with a queen bed and private patio.
Home in Great Barrington
Fridge, microwave, oven, stovetop

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Our family had a wonderful experience and stay. "
The price is AU$470
includes taxes & fees
1 Sept - 2 Sept
Home in Great Barrington
Bungalow in the Berkshires
Exterior

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (1)
"Renting this house was very last minute because the place we initially booked fell through - and we're so glad it did! The house was charming, cozy, up-to-date, and beautifully decorated. The neighborhood was nice and quiet, and the drive to downtown was short. I highly recommend this house!"
The price is AU$805
includes taxes & fees
24 Aug - 25 Aug
Bungalow in the Berkshires
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. "
The price is AU$781
includes taxes & fees
3 Sept - 4 Sept
Cheerful 3-bedroom cottage with woodstove
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

9.8 out of 10, Exceptional, (7)
"My wife, two kids, and chocolate lab spent a few days at the cottage to enjoy the snow and hot tub. Everything was set up exactly as described and Nicole was very friendly and proactive. We had a great time and would do it again "
The price is AU$612
includes taxes & fees
1 Sept - 2 Sept
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is AU$1,630
includes taxes & fees
25 Aug - 26 Aug
Hancock Village Inn at Jiminy Peak
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 AU$620
includes taxes & fees
3 Sept - 4 Sept
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
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 AU$1,239
includes taxes & fees
29 Aug - 30 Aug
Spacious 5-bedroom house in charming Lee with WiFi
Great Barrington Get Away
Fridge, microwave, oven, stovetop

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
The price is AU$887
includes taxes & fees
2 Sept - 3 Sept
Great Barrington Get Away
3-bedroom house in beautiful Berkshires, close to amenities!
Property grounds

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

The price is AU$500
includes taxes & fees
26 Aug - 27 Aug
3-bedroom house in beautiful Berkshires, close to amenities!
Elegant suite with a king bed, fireplace, and kitchenette.
Living area

Elegant suite with a king bed, fireplace, and kitchenette.

The price is AU$870
includes taxes & fees
1 Sept - 2 Sept
Elegant suite with a king bed, fireplace, and kitchenette.
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Fireplace

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

The price is AU$868
includes taxes & fees
7 Sept - 8 Sept
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Fireplace

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

The price is AU$712
includes taxes & fees
1 Sept - 2 Sept
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
"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 AU$774
includes taxes & fees
3 Sept - 4 Sept
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
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.
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Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Liked the fact there are 2 pools, an indoor and an outdoor."
MARK 2-night trip
Posted 2 days ago
Vacation Village in the Berkshires