Holiday Homes in The Berkshires

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Featured Holiday Homes in The Berkshires

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (259)
"We enjoyed our stay. Excellent location to explore Western Mass!"
The price is AU$351
includes taxes & fees
28 Oct - 29 Oct
Berkshire Village Carriage House - Super Private!!

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

2.0 star property
8.0 out of 10, Very good, (5)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is AU$741
includes taxes & fees
6 Oct - 7 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is AU$726
includes taxes & fees
6 Oct - 7 Oct
Comfortable Berkshires retreat on mtn resort, SISO

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 AU$591
includes taxes & fees
6 Oct - 7 Oct
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Enjoyed our stay!!!"
The price is AU$404
includes taxes & fees
3 Nov - 4 Nov
Home in Great Barrington

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

The price is AU$688
includes taxes & fees
28 Oct - 29 Oct
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

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. "
The price is AU$721
includes taxes & fees
5 Oct - 6 Oct
NEW RENO Historic Creamery in Berkshires w/hot tub

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 AU$795
includes taxes & fees
2 Nov - 3 Nov
Great Barrington Get Away

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 AU$769
includes taxes & fees
13 Oct - 14 Oct
Cheerful 3-bedroom cottage with woodstove

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$600
includes taxes & fees
28 Oct - 29 Oct
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

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 AU$818
includes taxes & fees
5 Oct - 6 Oct
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 AU$765
includes taxes & fees
5 Oct - 6 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (14)
"Amazing Inn. Cozy and everything we needed. "
The price is AU$1,702
includes taxes & fees
21 Oct - 22 Oct
Hancock Village Inn at Jiminy Peak

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (2)
"Great location, very clean and well appointed with everyth"
The price is AU$639
includes taxes & fees
16 Oct - 17 Oct
Bungalow in the Berkshires

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

10.0 out of 10, Exceptional, (1)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
The price is AU$2,157
includes taxes & fees
13 Oct - 14 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"

10.0 out of 10, Exceptional, (1)
"The host was exceptional and so kind. The location was in close proximity to 3 quaint New England small towns whose downtowns had many restaurants and local shops to enjoy-Great Barrington (GB Eats for breakfast), Stockbridge (best shopping) and Lenox (exceptional dinner at Frankie’s Italian). The house looked updated on the outside but inside looked like early 1900s with a hint of Victorian influence. My only caution is for anyone with mobility issues as all 3 bedrooms and the only (very small)...
The price is AU$485
includes taxes & fees
2 Nov - 3 Nov
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"

Spacious 5-bedroom house in charming Lee with WiFi

The price is AU$1,256
includes taxes & fees
21 Oct - 22 Oct
Spacious 5-bedroom house in charming Lee with WiFi

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

The price is AU$750
includes taxes & fees
9 Oct - 10 Oct
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

Historic Susan B. Anthony Room - Cozy & Charming Stay

The price is AU$546
includes taxes & fees
28 Oct - 29 Oct
Historic Susan B. Anthony Room - Cozy & Charming Stay

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

The price is AU$842
includes taxes & fees
9 Oct - 10 Oct
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
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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