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Our top choices for October Mountain State Forest vacation homes

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (146 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is AED 680
AED 1,258 total
includes taxes & fees
26 May - 27 May
Big farmhouse in the foothills of the Berkshires

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is AED 172
AED 1,037 total
includes taxes & fees
27 May - 28 May
Real Estate: Therapy - Lake, Laundry, Love it

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 588
AED 1,449 total
includes taxes & fees
3 Jun - 4 Jun
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

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 559
AED 1,444 total
includes taxes & fees
27 May - 28 May
Near Tanglewood: Historic Summer Retreat

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (31 reviews)
"Everything was as advertised!"
United States
Jessica S.
The price is AED 850
AED 1,314 total
includes taxes & fees
3 Jun - 4 Jun
Home in Great Barrington

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 536
AED 1,382 total
includes taxes & fees
27 May - 28 May
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Great location and nice size house for a family of 5. We had a couple hiccups but the host responded quickly and handled things promptly. "
United States
Jennifer L.
The price is AED 744
AED 1,163 total
includes taxes & fees
25 May - 26 May
Cozy Riverside 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
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is AED 643
AED 2,037 total
includes taxes & fees
24 May - 25 May
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

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 1,036
AED 2,124 total
includes taxes & fees
3 Jun - 4 Jun
Treetop Hideaway in Tyringham

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is AED 823
AED 1,782 total
includes taxes & fees
25 May - 26 May
Historic Berkshires Home Near Tanglewood, Trails & Wineries

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 635
AED 1,542 total
includes taxes & fees
24 May - 25 May
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

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
24 May - 25 May
Comfortable Berkshires retreat on mtn resort, SISO

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.6 out of 10, Exceptional, (4 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is AED 713
AED 1,238 total
includes taxes & fees
27 May - 28 May
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
The price is AED 871
AED 1,850 total
includes taxes & fees
25 May - 26 May
Cheerful 3-bedroom cottage with woodstove

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 988
AED 1,818 total
includes taxes & fees
24 May - 25 May
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is AED 1,102
AED 1,953 total
includes taxes & fees
24 May - 25 May
Cozy. Clean. Free bagel shop. 3 Fireplaces.

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, (1 review)
"My family and I had a lovely stay at Oscar’s Pond Estate! The house was clean and inviting, and provided everything we needed for a comfortable stay. The surrounding area provided beautiful views as we enjoyed the back deck and yard, complete with a hot tub and fire pit. I highly recommend the nearby Art Omi sculpture park if you stay here. It was a perfect outing for our 2 families with 4 kids ages 2 to 9. The owner was incredibly warm and responsive and provided clear and easy check-in...
United States
Betsy H.
The price is AED 1,025
AED 2,217 total
includes taxes & fees
26 May - 27 May
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Dreamy 6 Bedroom House, Come Enjoy Hillsdale!

Dreamy 6 Bedroom House, Come Enjoy Hillsdale!
Hillsdale
8.6 out of 10, Excellent, (4 reviews)
"Very nice stay. Evidence of cleaning as we could smell bleach when we arrived - we appreciated knowing things had been disinfected! Older house with older house quirks but perfect and comfortable for a group of 7 that wanted to hang out and cook and gab. Beds also very comfortable! Andrew provided all info before arriving and everything went smoothly."
United States
S V.
The price is AED 1,043
AED 2,901 total
includes taxes & fees
24 May - 25 May
Dreamy 6 Bedroom House, Come Enjoy Hillsdale!

Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam
Hillsdale
8.4 out of 10, Very Good, (5 reviews)
"Overall a very pleasant stay. It is a cool old house with all its charm and quirks. Very spacious, comfortable. Decent kitchen. Location very accessible for mountains and tooling around. Just right for a getaway"
United States
Annetta D.
The price is AED 1,124
AED 2,515 total
includes taxes & fees
24 May - 25 May
Perfect House In Hillsdale, Brings Friends & Fam

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
3 Jun - 4 Jun
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