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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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)
"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 ￥12,504
￥34,524 total
includes taxes & fees
Oct 29 - Oct 30
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 ￥13,454
￥35,651 total
includes taxes & fees
Nov 5 - Nov 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, (12 reviews)
"Absolutely wonderful place to stay. Quiet, clean, comfortable and close to a lot of things while feeling secluded. Owner communicated quickly and entry was easy. Loved every minute of our stay."
United States
Jeri R.
The price is ￥18,376
￥32,458 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Home in Pownal VT
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

4. 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, (9 reviews)
"A lovely house! Very convenient for a Tanglewood weekend."
United States
Robert B.
The price is ￥27,857
￥89,426 total
includes taxes & fees
Oct 28 - Oct 29
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Pool

5. 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 ￥25,483
￥86,395 total
includes taxes & fees
Oct 28 - Oct 29
Comfortable Berkshires retreat on mtn resort, SISO
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 ￥31,181
￥73,638 total
includes taxes & fees
Nov 18 - Nov 19
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A camping setup with a metal chair and a table by a river in a forest.

7. 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 ￥31,656
￥54,423 total
includes taxes & fees
Oct 28 - Oct 29
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A wooden deck with a table and chairs, surrounded by a white railing.

8. 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 ￥42,593
￥77,986 total
includes taxes & fees
Oct 25 - Oct 26
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.

9. 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 ￥23,077
￥59,369 total
includes taxes & fees
Oct 27 - Oct 28
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A modern living room with a sofa, ottoman, and a flat-screen TV mounted on the wall.

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

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is ￥49,858
￥109,390 total
includes taxes & fees
Nov 3 - Nov 4
Ellie’s Overlook, best view in the Berkshires!
A bedroom with a bed, a nightstand, a lamp, a chair, and a dresser.

11. Mayas Shangrila

Mayas Shangrila
2.0 star property
Richmond
The price is ￥129,337
￥184,423 total
includes taxes & fees
Oct 23 - Oct 24
Mayas Shangrila
A kitchen with white cabinets, a wooden dining table, and pendant lights.

12. 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 ￥36,246
￥76,201 total
includes taxes & fees
Oct 31 - Nov 1
A roomy remodeled retreat close to MassMoCA
A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery.

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)
"Loved the wellness hut. Our sauna didnt work however the room was spacious and comfy. The staff is very attentive and we also enjoyed the soup stroll. Would def recommend."
United States
Lauren C.
The price is ￥42,736
￥84,156 total
includes taxes & fees
Nov 3 - Nov 4
Treat yourself at the stunning June Farms Wellness Huts!
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

14. 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 ￥48,078
￥97,943 total
includes taxes & fees
Oct 26 - Oct 27
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A staircase with a wooden handrail and a white wall with a light switch.

15. 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 ￥27,778
￥44,641 total
includes taxes & fees
Oct 27 - Oct 28
Leaf-Peeper Paradise in the Berkshires
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

16. 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 ￥99,550
￥181,860 total
includes taxes & fees
Oct 27 - Oct 28
Hancock Village Inn Near Jiminy Peak
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 ￥50,286
￥100,369 total
includes taxes & fees
Oct 29 - Oct 30
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

18. 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 ￥34,188
￥53,392 total
includes taxes & fees
Nov 3 - Nov 4
Home in Great Barrington
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

19. 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 ￥59,988
￥109,970 total
includes taxes & fees
Nov 3 - Nov 4
Secluded Family Home in Serene Stockbridge Woods
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

20. 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 ￥44,125
￥72,601 total
includes taxes & fees
Nov 17 - Nov 18
Greylock Cabin
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
"Staff is awesome and this dog friendly hotel doesn’t feel dirty or different than any other boutique hotel."
Vicki 1-night trip
Posted 8 hours ago
Hotel On North

Find out more about Pittsfield State Forest

Pittsfield State Forest Vacation Homes information

Number of reviews
248
Accommodation
358 Vacation Homes
Lowest Price
￥32,458
Highest Price
￥181,860

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