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Our top choices for October Mountain State Forest vacation homes

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
2 Jul - 3 Jul
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (147 reviews)
"Great location"
United States
Will G.
The price is AED 628
AED 1,223 total
includes taxes & fees
14 Jul - 15 Jul
Big farmhouse in the foothills of the Berkshires

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 770
AED 1,673 total
includes taxes & fees
13 Jul - 14 Jul
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 AED 774
AED 1,680 total
includes taxes & fees
7 Jul - 8 Jul
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

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 777
AED 1,204 total
includes taxes & fees
7 Jul - 8 Jul
Cozy Riverside Berkshires Retreat

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 787
AED 1,605 total
includes taxes & fees
13 Jul - 14 Jul
stylish Berkshires Retreat

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.6 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 2,057 total
includes taxes & fees
9 Jul - 10 Jul
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is AED 367
AED 1,276 total
includes taxes & fees
16 Jul - 17 Jul
Real Estate: Therapy - Lake, Laundry, Love it

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 1,062
AED 1,592 total
includes taxes & fees
19 Jul - 20 Jul
Home in Great Barrington

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)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is AED 845
AED 1,395 total
includes taxes & fees
2 Jul - 3 Jul
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)
"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

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 871
AED 1,850 total
includes taxes & fees
13 Jul - 14 Jul
Cheerful 3-bedroom cottage with woodstove

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 1,117
AED 2,357 total
includes taxes & fees
20 Jul - 21 Jul
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

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 1,282
AED 2,183 total
includes taxes & fees
1 Aug - 2 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Unique and Eclectic Small Town Suite Rental in Massachusetts

Unique and Eclectic Small Town Suite Rental in Massachusetts
Cummington
10.0 out of 10, Exceptional, (1 review)
"So cozy and welcoming. It was a great spot to enjoy all the beauty the Berkshire Mountains have to offer."
United States
CJ L.
The price is AED 400
AED 501 total
includes taxes & fees
2 Jul - 3 Jul
Unique and Eclectic Small Town Suite Rental in Massachusetts

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 683
AED 2,097 total
includes taxes & fees
6 Jul - 7 Jul
Comfortable Berkshires retreat on mtn resort, SISO

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 1,735 total
includes taxes & fees
7 Jul - 8 Jul
Sweet Cozy Victorian in Housatonic. Close to everything.

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.
Berkshire House Stay: 5BR/5BA

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
Spacious 5-bedroom house in charming Lee with WiFi

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 1,238
AED 2,371 total
includes taxes & fees
6 Jul - 7 Jul
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
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 October Mountain State Forest Hotel Reviews