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Our top choices for Pittsfield vacation homes

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

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
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 ¥50,259
¥87,954 total
includes taxes & fees
Jun 14 - Jun 15
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (19 reviews)
"Really great host - communication was great. House is so close to skiing, can’t beat it "
United States
Stephanie B.
The price is ¥100,638
¥183,848 total
includes taxes & fees
Jun 16 - Jun 17
Hancock Village Inn Near Jiminy Peak

Unique and Eclectic Small Town Suite Rental in Massachusetts

Unique and Eclectic Small Town Suite Rental in Massachusetts
Cummington
The price is ¥17,281
¥21,648 total
includes taxes & fees
Jun 22 - Jun 23
Unique and Eclectic Small Town Suite Rental in Massachusetts

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is ¥13,249
¥52,511 total
includes taxes & fees
Jun 17 - Jun 18
Real Estate: Therapy - Lake, Laundry, Love it

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (2 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is ¥18,577
¥32,634 total
includes taxes & fees
Jun 15 - Jun 16
Cozy Home in Pownal VT

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ¥23,329
¥60,197 total
includes taxes & fees
Jun 15 - Jun 16
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (15 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ¥35,714
¥54,370 total
includes taxes & fees
Jun 14 - Jun 15
Cozy Riverside Berkshires Retreat

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ¥26,930
¥64,219 total
includes taxes & fees
Jun 23 - Jun 24
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
The price is ¥28,370
¥64,398 total
includes taxes & fees
Jun 16 - Jun 17
stylish Berkshires Retreat

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"the hosts were great very helpful and pleasant"
United States
Ron L.
The price is ¥37,802
¥65,469 total
includes taxes & fees
Jun 17 - Jun 18
The Greylock Cabin

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (32 reviews)
"Perfect space for an overnight stay. Very clean and well appointed. Communication from host was great and check in was a breeze. 2 minute drive from downtown Great Barrington."
United States
Anonymous traveler
The price is ¥38,162
¥58,355 total
includes taxes & fees
Jun 14 - Jun 15
Home in Great Barrington

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is ¥28,002
¥88,899 total
includes taxes & fees
Jun 14 - Jun 15
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (25 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is ¥32,402
¥71,760 total
includes taxes & fees
Jun 15 - Jun 16
North Getaway Cottage

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (6 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is ¥36,802
¥60,752 total
includes taxes & fees
Jun 14 - Jun 15
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is ¥23,185
¥60,915 total
includes taxes & fees
Jun 15 - Jun 16
Near Tanglewood: Historic Summer Retreat

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is ¥47,363
¥95,220 total
includes taxes & fees
Jun 15 - Jun 16
Treetop Hideaway in Tyringham

Treat yourself at the stunning June Farms Wellness Huts!

Treat yourself at the stunning June Farms Wellness Huts!
West Sand Lake
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
Treat yourself at the stunning June Farms Wellness Huts!

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is ¥28,082
¥65,502 total
includes taxes & fees
Jun 14 - Jun 15
Historic Berkshires Home Near Tanglewood, Trails & Wineries

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
8.0 out of 10, Very Good, (1 review)
"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "
United States
Luz A.
The price is ¥28,802
¥68,638 total
includes taxes & fees
Jun 14 - Jun 15
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is ¥44,283
¥79,698 total
includes taxes & fees
Jun 23 - Jun 24
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
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
155
Accommodation
426 Vacation Homes
Lowest Price
¥32,634
Highest Price
¥183,848