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Vacation Homes in Pittsfield

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 ¥22,121
¥33,770 total
includes taxes & fees
Oct 28 - Oct 29
Berkshire Village Carriage House - Super Private!!

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 ¥30,084
¥69,641 total
includes taxes & fees
Oct 7 - Oct 8
NEW RENO Historic Creamery in Berkshires w/hot tub

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 ¥39,684
¥71,508 total
includes taxes & fees
Oct 7 - Oct 8
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (14)
"Amazing Inn. Cozy and everything we needed. "
The price is ¥88,335
¥163,848 total
includes taxes & fees
Oct 21 - Oct 22
Hancock Village Inn at Jiminy Peak

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 ¥23,625
¥57,027 total
includes taxes & fees
Oct 7 - Oct 8
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

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 ¥23,890
¥57,817 total
includes taxes & fees
Oct 28 - Oct 29
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Enjoyed our stay!!!"
The price is ¥23,005
¥38,874 total
includes taxes & fees
Nov 3 - Nov 4
Home in Great Barrington

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 ¥32,915
¥73,993 total
includes taxes & fees
Oct 7 - Oct 8
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is ¥23,743
¥69,993 total
includes taxes & fees
Oct 7 - Oct 8
Comfortable Berkshires retreat on mtn resort, SISO

Riverbend Berkshire East Basecamp - 3 bedrooms available

The price is ¥23,595
¥62,101 total
includes taxes & fees
Oct 13 - Oct 14
Riverbend Berkshire East Basecamp - 3 bedrooms available

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (22)
"Very cozy and comfortable with everything we needed to make our stay enjoyable. The kitchen was well stocked, the bedrooms a good size with comfortable mattresses. The deck and the yard were lovely. This location is gem!"
The price is ¥26,279
¥61,971 total
includes taxes & fees
Oct 7 - Oct 8
Near Tanglewood: Historic Summer Retreat

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (2)
"Great location, very clean and well appointed with everyth"
The price is ¥44,241
¥61,607 total
includes taxes & fees
Oct 13 - Oct 14
Bungalow in the Berkshires

North Getaway Cottage

9.2 out of 10, Wonderful, (22)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is ¥38,342
¥76,597 total
includes taxes & fees
Nov 2 - Nov 3
North Getaway Cottage

Cozy. Clean. Free bagel shop.

10.0 out of 10, Exceptional, (10)
"The perfect location for a stay in Great Barrington. The house is so well done and very comfortable!"
The price is ¥58,988
¥97,846 total
includes taxes & fees
Nov 4 - Nov 5
Cozy. Clean. Free bagel shop.

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 ¥33,181
¥46,782 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"

The Lakeshore House

10.0 out of 10, Exceptional, (1)
"Excellent stay!"
The price is ¥71,523
¥118,259 total
includes taxes & fees
Oct 7 - Oct 8
The Lakeshore House

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 ¥42,029
¥76,597 total
includes taxes & fees
Nov 2 - Nov 3
Great Barrington Get Away

Experience Timeless Elegance in The Edith Wharton Room!

The price is ¥30,821
¥45,134 total
includes taxes & fees
Nov 2 - Nov 3
Experience Timeless Elegance in The Edith Wharton Room!

Treat yourself at the stunning June Farms Wellness Huts!

10.0 out of 10, Exceptional, (8)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
The price is ¥39,021
¥68,686 total
includes taxes & fees
Oct 15 - Oct 16
Treat yourself at the stunning June Farms Wellness Huts!

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 ¥103,082
¥220,896 total
includes taxes & fees
Oct 28 - Oct 29
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness 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.
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Top Pittsfield Hotel Reviews

Find out more about Pittsfield

Find out more about Pittsfield

Pittsfield Vacation Homes information

Number of reviews
12,777
Accommodation
471 Vacation Homes
Lowest Price
¥13,176
Highest Price
¥25,037