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

2.0 star property
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (16)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
Hancock Village Inn Near Jiminy Peak

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest
9.6 out of 10, Exceptional, (10)
"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."
United States
James D.
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Florida Mountain Log Cabin

2.0 star property
Florida
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
Florida Mountain Log Cabin

Home in Great Barrington

Great Barrington
9.8 out of 10, Exceptional, (25)
"Enjoyed our stay!!!"
United States
Fred W.
Home in Great Barrington

North Getaway Cottage

Williamstown
9.2 out of 10, Wonderful, (24)
"The cottage was the perfect accommodations for our overnight stay in town for a funeral. Thank you Claudia. "
United States
Mary Alice H.
North Getaway Cottage

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic
10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
Sweet Cozy Victorian in Housatonic. Close to everything.

Treat yourself at the stunning June Farms Wellness Huts!

West Sand Lake
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."
United States
SteveS
Treat yourself at the stunning June Farms Wellness Huts!

Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale
8.4 out of 10, Very good, (5)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
United States
Stefanie K.
Perfect House In Hillsdale, Brings Friends & Fam

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.4 out of 10, Exceptional, (6)
Pet Friendly Riverfront Home in Great Barrington

The Greylock Cabin

Florida
10.0 out of 10, Exceptional, (4)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveller
The Greylock Cabin

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont
Riverbend Berkshire East Basecamp - 3 bedrooms available

Great Barrington Get Away

Great Barrington
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
Great Barrington Get Away

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Valatie
10.0 out of 10, Exceptional, (57)
"Great spot on the lake. Super quiet and relaxing."
United States
vincent m.
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Artists’ Hideaway in Old Chatham

Old Chatham
Artists’ Hideaway in Old Chatham

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

Great Barrington
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!"
United States
Roberta
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
Spacious 5-bedroom house in charming Lee with WiFi

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Hancock
9.8 out of 10, Exceptional, (72)
"Great communication. Lots of games for the kids. Comfortable beds. Great living and game room. "
United States
Samuel R.
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
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

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Pittsfield Vacation Homes information

Number of reviews
273
Accommodation
421 Vacation Homes
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