Holiday Homes in Pittsfield

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Our top choices for Pittsfield holiday 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 €465
includes taxes & fees
8 Jun - 9 Jun
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 €986
includes taxes & fees
3 Jun - 4 Jun
Hancock Village Inn Near Jiminy Peak

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 €322
includes taxes & fees
3 Jun - 4 Jun
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

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 €336
includes taxes & fees
3 Jun - 4 Jun
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is €251
includes taxes & fees
7 Jun - 8 Jun
Real Estate: Therapy - Lake, Laundry, Love it

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 €351
includes taxes & fees
3 Jun - 4 Jun
The Greylock Cabin

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
The price is €334
includes taxes & fees
3 Jun - 4 Jun
stylish Berkshires Retreat

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 €178
includes taxes & fees
7 Jun - 8 Jun
Cozy Home in Pownal VT

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Great location and nice size house for a family of 5. We had a couple hiccups but the host responded quickly and handled things promptly. "
United States
Jennifer L.
The price is €269
includes taxes & fees
3 Jun - 4 Jun
Cozy Riverside Berkshires Retreat

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 €333
includes taxes & fees
3 Jun - 4 Jun
Near Tanglewood: Historic Summer Retreat

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 €474
includes taxes & fees
3 Jun - 4 Jun
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 €379
includes taxes & fees
3 Jun - 4 Jun
North Getaway Cottage

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (31 reviews)
"Everything was as advertised!"
United States
Jessica S.
The price is €300
includes taxes & fees
14 Jun - 15 Jun
Home in Great Barrington

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 €344
includes taxes & fees
3 Jun - 4 Jun
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.6 out of 10, Exceptional, (5 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is €291
includes taxes & fees
4 Jun - 5 Jun
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

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 €495
includes taxes & fees
3 Jun - 4 Jun
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
The price is €425
includes taxes & fees
4 Jun - 5 Jun
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 €368
includes taxes & fees
10 Jun - 11 Jun
Historic Berkshires Home Near Tanglewood, Trails & Wineries

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (2 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is €442
includes taxes & fees
4 Jun - 5 Jun
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is €451
includes taxes & fees
4 Jun - 5 Jun
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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 Holiday Homes information

Number of reviews
153
Accommodation
425 Holiday Homes
Lowest Price
€178
Highest Price
€986