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Our top choices for Pittsfield holiday homes

The price is HK$1,669
HK$2,701 total
includes taxes & fees
16 Feb - 17 Feb
3-bedroom house in beautiful Berkshires, close to amenities!
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is HK$2,098
HK$3,850 total
includes taxes & fees
22 Jan - 23 Jan
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
10.0 out of 10, Exceptional, (16 reviews)
"Great place for a family reunion. Lots of bedrooms and bathrooms. Kitchen is large & well equipped"
United States
Veronica and Mark W.
The price is HK$4,905
HK$8,961 total
includes taxes & fees
27 Jan - 28 Jan
Hancock Village Inn Near Jiminy Peak
9.6 out of 10, Exceptional, (10 reviews)
"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.
The price is HK$1,249
HK$3,076 total
includes taxes & fees
28 Jan - 29 Jan
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Holiday Home in Florida

Florida Mountain Log Cabin
2.0 star property
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is HK$1,433
HK$2,651 total
includes taxes & fees
22 Jan - 23 Jan
Florida Mountain Log Cabin

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is HK$1,137
HK$1,949 total
includes taxes & fees
26 Jan - 27 Jan
Home in Great Barrington

Holiday Home in New Lebanon

Near Tanglewood: Historic Summer Retreat
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is HK$913
HK$2,717 total
includes taxes & fees
1 Feb - 2 Feb
Near Tanglewood: Historic Summer Retreat
10.0 out of 10, Exceptional, (2 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is HK$1,247
HK$3,292 total
includes taxes & fees
27 Jan - 28 Jan
Riverbend Berkshire East Basecamp - 3 bedrooms available
2.0 star property
8.0 out of 10, Very good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
The price is HK$1,364
HK$4,332 total
includes taxes & fees
22 Jan - 23 Jan
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
10.0 out of 10, Exceptional, (8 reviews)
"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
The price is HK$1,937
HK$3,492 total
includes taxes & fees
25 Jan - 26 Jan
Treat yourself at the stunning June Farms Wellness Huts!
9.6 out of 10, Exceptional, (4 reviews)
"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."
United States
Sarah D.
The price is HK$1,403
HK$3,588 total
includes taxes & fees
1 Feb - 2 Feb
Sun Filled Lenox Retreat - Minutes to Tanglewood!
2.0 star property
The price is HK$1,364
HK$2,375 total
includes taxes & fees
25 Jan - 26 Jan
Renovated house. Built in 1890s. No neighbors in sight.
10.0 out of 10, Exceptional, (1 review)
"Fantastic place to stay!"
United States
James
The price is HK$1,661
HK$2,131 total
includes taxes & fees
26 Jan - 27 Jan
Suite 3 - Quiet and private accommodations in a country setting.

Holiday Home in Florida

The Greylock Cabin
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveller
The price is HK$1,843
HK$3,175 total
includes taxes & fees
17 Feb - 18 Feb
The Greylock Cabin

Holiday Home in Great Barrington

Family Ski Getaway in the Berkshires
9.2 out of 10, Wonderful, (7 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,579
HK$2,322 total
includes taxes & fees
26 Jan - 27 Jan
Family Ski Getaway in the Berkshires
10.0 out of 10, Exceptional, (3 reviews)
"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.
The price is HK$1,053
HK$2,090 total
includes taxes & fees
5 Feb - 6 Feb
Sweet Cozy Victorian in Housatonic. Close to everything.
9.0 out of 10, Wonderful, (21 reviews)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
The price is HK$1,046
HK$2,892 total
includes taxes & fees
2 Feb - 3 Feb
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Holiday Home in Old Chatham

Artists’ Hideaway in Old Chatham
The price is HK$1,258
HK$4,002 total
includes taxes & fees
22 Jan - 23 Jan
Artists’ Hideaway in Old Chatham
10.0 out of 10, Exceptional, (33 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is HK$2,331
HK$5,069 total
includes taxes & fees
22 Jan - 23 Jan
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10.0 out of 10, Exceptional, (3 reviews)
"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
The price is HK$4,414
HK$10,356 total
includes taxes & fees
22 Jan - 23 Jan
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

Pittsfield Vacation Homes information

Number of reviews
158
Accommodation
417 Vacation Homes
Lowest Price
HK$1,949
Highest Price
HK$10,356

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