Berkshire mountains in Autumn

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for October Mountain State Forest vacation homes

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 643
AED 2,037 total
includes taxes & fees
21 Jun - 22 Jun
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
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
22 Jun - 23 Jun
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Property grounds

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)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is AED 698
AED 1,305 total
includes taxes & fees
2 Jul - 3 Jul
Big farmhouse in the foothills of the Berkshires
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is AED 364
AED 1,268 total
includes taxes & fees
16 Jul - 17 Jul
Real Estate: Therapy - Lake, Laundry, Love it
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 542
AED 1,373 total
includes taxes & fees
22 Jun - 23 Jun
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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 760
AED 1,666 total
includes taxes & fees
30 Jun - 1 Jul
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (32 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 876
AED 1,348 total
includes taxes & fees
22 Jun - 23 Jun
Home in Great Barrington
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 1,764 total
includes taxes & fees
28 Jun - 29 Jun
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 744
AED 1,155 total
includes taxes & fees
22 Jun - 23 Jun
Cozy Riverside Berkshires Retreat
Dining

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is AED 735
AED 1,234 total
includes taxes & fees
21 Jun - 22 Jun
Sugar Shack - 300 square feet of pure sweetness.
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, (6 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
21 Jun - 22 Jun
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Exterior

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 AED 826
AED 1,769 total
includes taxes & fees
23 Jun - 24 Jun
Near Tanglewood: Historic Summer Retreat
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
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 2,019 total
includes taxes & fees
21 Jun - 22 Jun
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Property grounds

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
12 Jul - 13 Jul
Cheerful 3-bedroom cottage with woodstove
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 885
AED 2,040 total
includes taxes & fees
23 Jun - 24 Jun
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Private kitchen

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 AED 992
AED 1,999 total
includes taxes & fees
13 Jul - 14 Jul
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
Property grounds

Unique and Eclectic Small Town Suite Rental in Massachusetts

Unique and Eclectic Small Town Suite Rental in Massachusetts
Cummington
The price is AED 400
AED 501 total
includes taxes & fees
21 Jun - 22 Jun
Unique and Eclectic Small Town Suite Rental in Massachusetts
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 1,997 total
includes taxes & fees
23 Jun - 24 Jun
Comfortable Berkshires retreat on mtn resort, SISO
Fridge, microwave, oven, stovetop

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.
The price is AED 1,745
AED 3,163 total
includes taxes & fees
30 Jun - 1 Jul
Spacious 5-bedroom house in charming Lee with WiFi
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Our experience at the Red Lion Inn went beyond our expectations. The entire staff was most helpful, went above and beyond to make our stay enjoyable, and treated us as if we were the only guests staying there! The inn is magnificent and we felt we were staying in a museum! The accommodation was lovely and the dining room served gourmet food. We would love to go back. If you haven’t stayed there you are missing out on a great opportunity."
Marinus 2-night trip
Posted 6 hours ago
The Red Lion Inn

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