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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Pittsfield holiday 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
8.0 out of 10, Very good, (8 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$2,737
HK$4,643 total
includes taxes & fees
8 Aug - 9 Aug
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, (21 reviews)
"Really great host - communication was great. House is so close to skiing, can’t beat it "
United States
Stephanie B.
The price is HK$4,521
HK$8,489 total
includes taxes & fees
14 Jul - 15 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
10.0 out of 10, Exceptional, (1 review)
"Staff was super friendly, host was also amazing!"
United States
Connor
The price is HK$855
HK$1,069 total
includes taxes & fees
11 Jul - 12 Jul
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 HK$910
HK$1,608 total
includes taxes & fees
15 Jul - 16 Jul
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 HK$1,687
HK$3,619 total
includes taxes & fees
14 Jul - 15 Jul
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is HK$714
HK$2,637 total
includes taxes & fees
16 Jul - 17 Jul
Real Estate: Therapy - Lake, Laundry, Love it
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (18 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is HK$1,652
HK$2,563 total
includes taxes & fees
13 Jul - 14 Jul
Cozy Riverside Berkshires Retreat
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"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 HK$1,376
HK$3,053 total
includes taxes & fees
13 Jul - 14 Jul
stylish Berkshires Retreat
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 HK$1,553
HK$3,469 total
includes taxes & fees
13 Jul - 14 Jul
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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 traveller
The price is HK$2,059
HK$3,463 total
includes taxes & fees
15 Jul - 16 Jul
The Greylock Cabin
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 HK$1,380
HK$4,374 total
includes taxes & fees
16 Jul - 17 Jul
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
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)
"The location was excellent, within walking distance of ski trail. Wonderful view of the ski area and surrounding mountains. The fireplace was perfect for the end of the day. Our large family had plenty of space to have fun together or chill alone. We had concerns about the cleanliness and working conditions of some electronics. Our concerns were communicated with the owner, and the response was positive. I am sure with corrections this Comfortable Berkshire Retreat will be a 5 star stay. "
United States
Russell R.
The price is HK$1,263
HK$4,254 total
includes taxes & fees
9 Jul - 10 Jul
Comfortable Berkshires retreat on mtn resort, SISO
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (33 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
The price is HK$2,040
HK$3,093 total
includes taxes & fees
19 Jul - 20 Jul
Home in Great Barrington
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, (9 reviews)
"Great experience! Only there for one night because our son had a wrestling tournament. Wish we would have had more time at property. "
United States
Rochelle F.
The price is HK$1,804
HK$2,995 total
includes taxes & fees
9 Jul - 10 Jul
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 HK$2,361
HK$4,954 total
includes taxes & fees
28 Jul - 29 Jul
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is HK$2,878
HK$5,371 total
includes taxes & fees
14 Jul - 15 Jul
Treetop Hideaway in Tyringham
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.
Sweet Cozy Victorian in Housatonic. Close to everything.
Property grounds

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (4 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is HK$4,433
HK$7,315 total
includes taxes & fees
15 Jul - 16 Jul
Riverbend Berkshire East Basecamp - 3 bedrooms available
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.
The price is HK$2,280
HK$4,376 total
includes taxes & fees
9 Jul - 10 Jul
Treat yourself at the stunning June Farms Wellness Huts!
Smart TV, books

Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
8.0 out of 10, Very good, (1 review)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is HK$2,626
HK$5,053 total
includes taxes & fees
13 Jul - 14 Jul
Spacious Central Berkshires Home for Groups
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

10/10 Excellent
"Was fine, good location , clean sheets."
Yaniv 3-night trip
Posted 4 hours ago
Quality Inn Great Barrington

Find out more about Pittsfield

Pittsfield Vacation Homes information

Number of reviews
148
Accommodation
449 Vacation Homes
Lowest Price
HK$1,069
Highest Price
HK$8,489

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