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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Pittsfield State Forest vacation homes

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 AED 400
AED 501 total
includes taxes & fees
5 Jul - 6 Jul
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
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 859
AED 1,789 total
includes taxes & fees
21 Jul - 22 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 traveler
The price is AED 964
AED 1,622 total
includes taxes & fees
9 Jul - 10 Jul
The Greylock Cabin
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 AED 1,326
AED 2,489 total
includes taxes & fees
6 Jul - 7 Jul
Treetop Hideaway in Tyringham
Fridge, microwave, stovetop, dishwasher

Berkshire House Stay: 5BR/5BA

Berkshire House Stay: 5BR/5BA
Lee
10.0 out of 10, Exceptional, (22 reviews)
"Wonderful stay, beautiful, well equipped and clean property. Highly recommend for an adult famiky getaway "
United States
jennifer r.
The price is AED 2,270
AED 4,070 total
includes taxes & fees
16 Jul - 17 Jul
Berkshire House Stay: 5BR/5BA
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 AED 1,230
AED 2,366 total
includes taxes & fees
14 Jul - 15 Jul
Spacious Central Berkshires Home for Groups
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 774
AED 1,594 total
includes taxes & fees
14 Jul - 15 Jul
stylish Berkshires Retreat
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 AED 1,282
AED 2,199 total
includes taxes & fees
26 Jul - 27 Jul
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Property grounds

Enjoy comfortable elegance in this secluded grand home located in town

Enjoy comfortable elegance in this secluded grand home located in town
Lenox
10.0 out of 10, Exceptional, (80 reviews)
"Amazing property, close to town "
United States
Tricia E.
The price is AED 2,204
AED 2,814 total
includes taxes & fees
19 Jul - 20 Jul
Enjoy comfortable elegance in this secluded grand home located in town
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (39 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is AED 2,384
AED 4,025 total
includes taxes & fees
19 Jul - 20 Jul
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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 AED 1,058
AED 1,580 total
includes taxes & fees
16 Jul - 17 Jul
Home in Great Barrington
TV, fireplace, stereo

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington, Cabin Sleeps 14, Walk To Town
Great Barrington
9.6 out of 10, Exceptional, (48 reviews)
"The host was wonderful and the place was amazing!"
United States
James M.
The price is AED 6,222
AED 9,409 total
includes taxes & fees
2 Aug - 3 Aug
Great Barrington, Cabin Sleeps 14, Walk To Town
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 AED 744
AED 1,163 total
includes taxes & fees
7 Jul - 8 Jul
Cozy Riverside Berkshires Retreat
TV, stereo, offices

Perfect Nature Haven In Great Barrington

Perfect Nature Haven In Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (8 reviews)
"Their place was one of the cleanest rental cabins we have ever been, the house is in a great location with beautiful surroundings, the check in and check out was extremely easy for a family with little kids, loved the place and we hope to be back!"
United States
Ethel B.
The price is AED 3,140
AED 6,376 total
includes taxes & fees
5 Jul - 6 Jul
Perfect Nature Haven In Great Barrington
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 1,084
AED 1,719 total
includes taxes & fees
6 Jul - 7 Jul
Sweet Cozy Victorian in Housatonic. Close to everything.
Pool

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (74 reviews)
"Helpful host, lovely condo. Great location. Clean, tons of games and movies in unit. Also plenty of coffee pods included!"
United States
Christy F.
The price is AED 1,094
AED 2,174 total
includes taxes & fees
6 Jul - 7 Jul
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
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 AED 591
AED 1,993 total
includes taxes & fees
5 Jul - 6 Jul
Comfortable Berkshires retreat on mtn resort, SISO
TV, fireplace, printers

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (6 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 AED 2,079
AED 4,879 total
includes taxes & fees
14 Jul - 15 Jul
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Lobby

Modern Designer Chalet on 5.5 Private Acres Near Tanglewood

Modern Designer Chalet on 5.5 Private Acres Near Tanglewood
West Stockbridge
10.0 out of 10, Exceptional, (5 reviews)
"The home was great! It was tucked away but still very close to everything! Our family enjoyed our stay and Michelle was very welcoming and had everything at the house for us to feel comfortable."
United States
Jon U.
Modern Designer Chalet on 5.5 Private Acres Near Tanglewood
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 749 total
includes taxes & fees
6 Jul - 7 Jul
Cozy Home in Pownal VT
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 State Forest Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"We stayed overnight in a king suite. It was very well-equipped and spacious and we wished we were staying longer. The staff are very friendly and the location is great - near a grocery store and great specialty market, restaurants, and a short drive to Tanglewood and other attractions. We didn’t use the resort amenities, but will check them out next time!"
Nancy 1-night trip
Posted 3 hours ago
Berkshire Mountain Lodge