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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Pittsfield vacation homes

Outdoor dining

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 AED 1,154
AED 2,027 total
includes taxes & fees
29 Jun - 30 Jun
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Outdoor dining

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (20 reviews)
"Really great host - communication was great. House is so close to skiing, can’t beat it "
United States
Stephanie B.
The price is AED 2,117
AED 3,976 total
includes taxes & fees
30 Jun - 1 Jul
Hancock Village Inn Near Jiminy Peak
Property grounds

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
The price is AED 400
AED 501 total
includes taxes & fees
28 Jun - 29 Jun
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Dining

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (3 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 AED 426
AED 753 total
includes taxes & fees
29 Jun - 30 Jun
Cozy Home in Pownal VT
Outdoor spa tub

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 AED 714
AED 1,589 total
includes taxes & fees
29 Jun - 30 Jun
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
10.0 out of 10, Exceptional, (1 review)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is AED 793
AED 1,625 total
includes taxes & fees
30 Jun - 1 Jul
stylish Berkshires Retreat
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (16 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AED 793
AED 1,219 total
includes taxes & fees
1 Jul - 2 Jul
Cozy Riverside Berkshires Retreat
Exterior

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful cabin in a beautiful location. Host is amazing, very responsive. "
United States
Anonymous traveler
The price is AED 868
AED 1,503 total
includes taxes & fees
26 Jul - 27 Jul
The Greylock Cabin
Exterior

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 AED 744
AED 1,655 total
includes taxes & fees
29 Jun - 30 Jun
North Getaway Cottage
Fridge, microwave, stovetop, dishwasher

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.6 out of 10, Exceptional, (4 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is AED 646
AED 2,053 total
includes taxes & fees
28 Jun - 29 Jun
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Interior

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 AED 848
AED 1,772 total
includes taxes & fees
13 Jul - 14 Jul
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Property grounds

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, (7 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is AED 845
AED 1,403 total
includes taxes & fees
29 Jun - 30 Jun
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Exterior detail

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, (3 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 AED 948
AED 2,123 total
includes taxes & fees
28 Jun - 29 Jun
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
Real Estate: Therapy - Lake, Laundry, Love it
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (33 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 AED 1,062
AED 1,592 total
includes taxes & fees
19 Jul - 20 Jul
Home in Great Barrington
Terrace/patio

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)
"Loved the wellness hut. Our sauna didnt work however the room was spacious and comfy. The staff is very attentive and we also enjoyed the soup stroll. Would def recommend."
United States
Lauren C.
Treat yourself at the stunning June Farms Wellness Huts!
Property grounds

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts
Cummington
10.0 out of 10, Exceptional, (3 reviews)
"We loved out stay! The lodge was simply magical. Our host was quite easy to connect with! We hope to visit again soon."
United States
Mary D.
The price is AED 400
AED 501 total
includes taxes & fees
29 Jun - 30 Jun
Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts
TV

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 AED 1,260
AED 2,411 total
includes taxes & fees
30 Jun - 1 Jul
Treetop Hideaway in Tyringham
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very Good, (10 reviews)
"Kind and responsive host."
United States
Javier
The price is AED 591
AED 1,993 total
includes taxes & fees
28 Jun - 29 Jun
Comfortable Berkshires retreat on mtn resort, SISO
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (7 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is AED 1,205
AED 1,875 total
includes taxes & fees
26 Jul - 27 Jul
Sweet Cozy Victorian in Housatonic. Close to everything.
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

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"Well-located just off main street and a block from restaurants and shops. Rooms were spacious and clean. Reception staff were helpful. Breakfast a good way to start the day with decent choices. Reasonably priced, given the area."
David 2-night trip
Posted 4 hours ago
Quality Inn Great Barrington

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