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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Pittsfield State Forest vacation homes

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

1. 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)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is ￥11,020
￥32,569 total
includes taxes & fees
Oct 4 - Oct 5
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

2. 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 ￥14,011
￥36,265 total
includes taxes & fees
Oct 5 - Oct 6
1800s Carriage house in Berkshires / Hudson Valley
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

3. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (9 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 ￥18,347
￥32,230 total
includes taxes & fees
Oct 8 - Oct 9
Cozy Home in Pownal VT
Pool

4. 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 owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is ￥25,443
￥86,082 total
includes taxes & fees
Oct 4 - Oct 5
Comfortable Berkshires retreat on mtn resort, SISO
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

5. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is ￥27,708
￥88,248 total
includes taxes & fees
Oct 5 - Oct 6
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A white two-story house with a porch, surrounded by trees and a hill.

6. 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 ￥37,783
￥81,599 total
includes taxes & fees
Oct 7 - Oct 8
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A wooden deck with a table and chairs, surrounded by a white railing.

7. 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
8.4 out of 10, Very good, (10 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 ￥42,364
￥77,743 total
includes taxes & fees
Oct 14 - Oct 15
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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.

8. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥24,747
￥61,359 total
includes taxes & fees
Oct 7 - Oct 8
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

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

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is ￥49,590
￥108,111 total
includes taxes & fees
Oct 6 - Oct 7
Ellie’s Overlook, best view in the Berkshires!
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

10. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is ￥48,002
￥97,788 total
includes taxes & fees
Oct 7 - Oct 8
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A camping setup with a metal chair and a table by a river in a forest.

11. 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, (15 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 ￥31,486
￥53,778 total
includes taxes & fees
Oct 4 - Oct 5
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A modern building with a wooden deck and a door.

12. 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, (5 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 ￥40,298
￥95,754 total
includes taxes & fees
Oct 5 - Oct 6
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery and trees.

13. Treat yourself at the stunning June Farms Wellness Huts!

Treat yourself at the stunning June Farms Wellness Huts!
West Sand Lake
10.0 out of 10, Exceptional, (8 reviews)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
United States
SteveS
The price is ￥45,776
￥77,896 total
includes taxes & fees
Oct 12 - Oct 13
Treat yourself at the stunning June Farms Wellness Huts!
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

14. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is ￥33,375
￥52,755 total
includes taxes & fees
Oct 26 - Oct 27
Home in Great Barrington
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

15. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is ￥99,016
￥180,710 total
includes taxes & fees
Oct 6 - Oct 7
Hancock Village Inn Near Jiminy Peak
A kitchen with white cabinets, a wooden dining table, and pendant lights.

16. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is ￥36,051
￥75,615 total
includes taxes & fees
Oct 14 - Oct 15
A roomy remodeled retreat close to MassMoCA
A living room with a sofa, armchairs, a coffee table, and a television.

17. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (11 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 ￥55,785
￥107,500 total
includes taxes & fees
Oct 19 - Oct 20
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

18. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (27 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 ￥31,880
￥49,854 total
includes taxes & fees
Oct 4 - Oct 5
Leaf-Peeper Paradise in the Berkshires
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

19. Greylock Cabin

Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
The price is ￥44,056
￥72,487 total
includes taxes & fees
Oct 29 - Oct 30
Greylock Cabin
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

20. 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)
"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 ￥31,486
￥54,866 total
includes taxes & fees
Oct 8 - Oct 9
Sweet Cozy Victorian in Housatonic. Close to everything.
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

Hotel On North

Hotel On North

10/10 Excellent
"Delightful place with charm and warmth and character. I would love to come back."
Richard 1-night trip
Posted 10 hours ago
Hotel On North

Find out more about Pittsfield State Forest

Pittsfield State Forest Vacation Homes information

Number of reviews
254
Accommodation
346 Vacation Homes
Lowest Price
￥32,230
Highest Price
￥180,710

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