Holiday Homes in The Berkshires

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in The Berkshires

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 NZ$884
includes taxes & fees
11 Sept - 12 Sept
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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 NZ$532
includes taxes & fees
19 Aug - 20 Aug
Home in Great Barrington
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 NZ$805
includes taxes & fees
10 Sept - 11 Sept
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 NZ$747
includes taxes & fees
18 Aug - 19 Aug
North Getaway Cottage
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! "
The price is NZ$918
includes taxes & fees
18 Aug - 19 Aug
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
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 NZ$695
includes taxes & fees
1 Sept - 2 Sept
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
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 NZ$765
includes taxes & fees
1 Sept - 2 Sept
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
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 NZ$667
includes taxes & fees
1 Sept - 2 Sept
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Cheerful 3-bedroom cottage with woodstove
Property grounds

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 NZ$826
includes taxes & fees
14 Sept - 15 Sept
Cheerful 3-bedroom cottage with woodstove
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 NZ$953
includes taxes & fees
1 Sept - 2 Sept
Great Barrington Get Away
Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.
Property grounds

Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.

10.0 out of 10, Exceptional, (4)
"The property was spacious and very comfortable, had everything we needed. The area was also nice and fun to explore. "
Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.
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 NZ$865
includes taxes & fees
24 Aug - 25 Aug
Bungalow in the Berkshires
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 NZ$867
includes taxes & fees
1 Sept - 2 Sept
Sun Filled Lenox Retreat - Minutes to Tanglewood!
3-bedroom house in beautiful Berkshires, close to amenities!
Property grounds

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

The price is NZ$537
includes taxes & fees
26 Aug - 27 Aug
3-bedroom house in beautiful Berkshires, close to amenities!
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 NZ$1,768
includes taxes & fees
20 Aug - 21 Aug
Hancock Village Inn at Jiminy Peak
Historic Susan B. Anthony Room - Cozy & Charming Stay
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

The price is NZ$604
includes taxes & fees
1 Sept - 2 Sept
Historic Susan B. Anthony Room - Cozy & Charming Stay
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 NZ$571
includes taxes & fees
1 Sept - 2 Sept
Cozy Carriage House room with a double bed and private balcony
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 NZ$504
includes taxes & fees
1 Sept - 2 Sept
Experience Timeless Elegance in The Edith Wharton Room!
"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 NZ$834
includes taxes & fees
2 Sept - 3 Sept
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Elegant suite with a king bed, fireplace, and kitchenette.
Living area

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

The price is NZ$935
includes taxes & fees
1 Sept - 2 Sept
Elegant suite with a king bed, fireplace, and kitchenette.
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Nice place to hang your hat. It’s basic but very clean. Good location. Breakfasts were lovely and fresh!"
Frank 7-night trip
Posted 16 hours ago
The Yankee, Trademark Collection by Wyndham