A mountainous landscape with autumn foliage and a partly cloudy sky.

Holiday Homes in October Mountain State Forest

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for October Mountain State Forest holiday homes

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

1. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is AU$418
includes taxes & fees
3 Nov - 4 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

2. 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, (10 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$520
includes taxes & fees
28 Oct - 29 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A hot tub with a string of lights above it, set against a dark night sky.

3. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (19 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AU$544
includes taxes & fees
28 Oct - 29 Oct
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

4. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is AU$301
includes taxes & fees
29 Oct - 30 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

5. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is AU$326
includes taxes & fees
5 Nov - 6 Nov
1800s Carriage house in Berkshires / Hudson Valley
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

6. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 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 AU$772
includes taxes & fees
16 Nov - 17 Nov
Treetop Hideaway in Tyringham
A dining area with a wooden table, chairs, and a ceiling fan.

7. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is AU$395
includes taxes & fees
28 Oct - 29 Oct
Leaf-Peeper Paradise in the Berkshires
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

8. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (40 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is AU$471
includes taxes & fees
9 Nov - 10 Nov
Home in Great Barrington
A residential area with houses, a grassy yard, and a yellow boat.

9. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
The price is AU$875
includes taxes & fees
28 Oct - 29 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

10. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is AU$918
includes taxes & fees
2 Nov - 3 Nov
Secluded Family Home in Serene Stockbridge Woods
A dining area with a wooden table and chairs, a view of greenery and mountains through large windows, and a balcony with a railing.

11. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay in the Berkshires! The house was lovely, very clean, and such a cozy place to spend a fall weekend. The overlook was absolutely stunning, especially with all the beautiful fall foliage! We loved that the property felt peaceful and tucked away while still being a short drive to Lenox, nearby towns, and plenty of great hiking trails. The host was so kind and always quick to respond, which made everything easy from start to finish. We really enjoyed our stay and would...
United States
Delaney M.
The price is AU$990
includes taxes & fees
2 Nov - 3 Nov
Ellie’s Overlook, best view in the Berkshires!
A modern living room with a sofa, armchair, coffee table, and TV.

12. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.6 out of 10, Exceptional, (4 reviews)
"house was very clean, spacious and well equipped with everything we needed. Great communication with the host. Perfect location for our trip to Tanglewood."
United States
neil s.
The price is AU$835
includes taxes & fees
1 Nov - 2 Nov
Spacious Central Berkshires Home for Groups
A white two-story house with a porch, surrounded by trees and a hill.

13. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is AU$651
includes taxes & fees
2 Nov - 3 Nov
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

14. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is AU$483
includes taxes & fees
29 Oct - 30 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
A wooden deck with a table and chairs, surrounded by a white railing.

15. 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
8.6 out of 10, Excellent, (11 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
The price is AU$689
includes taxes & fees
28 Oct - 29 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

16. 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, (42 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveller
The price is AU$1,193
includes taxes & fees
23 Nov - 24 Nov
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Pool

17. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (12 reviews)
"Host was proactive in communication and answer each and every question."
United States
Amit
The price is AU$751
includes taxes & fees
29 Oct - 30 Oct
Comfortable Berkshires retreat on mtn resort, SISO
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

18. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.2 out of 10, Wonderful, (10 reviews)
"A lovely house! Very convenient for a Tanglewood weekend."
United States
Robert B.
The price is AU$839
includes taxes & fees
28 Oct - 29 Oct
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A house with a porch, a garden with pink flowers, and a stone wall along the road.

19. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (154 reviews)
"Great place and stunning location. Absolutely loved the quiet and perfect mix of old times with modern convenience. Had a short stay this trip but intend on returning in the future."
United States
Dale B.
The price is AU$505
includes taxes & fees
28 Oct - 29 Oct
Big farmhouse in the foothills of the Berkshires
A camping setup with a metal chair and a table by a river in a forest.

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (16 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is AU$475
includes taxes & fees
28 Oct - 29 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

10/10 Excellent
"Amazing property- feels luxurious because of the way it is perched up on a hill. We got a room on 4th floor with direct view of the fall colors on the mountains- that was amazing and a surprise"
manish 2-night trip
Posted 4 hours ago
Courtyard by Marriott Lenox Berkshires

Find out more about October Mountain State Forest

October Mountain State Forest Holiday Homes information

Number of reviews
364
Accommodation
391 Holiday Homes
Lowest Price
AU$301
Highest Price
AU$1,193

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