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Holiday Homes in Pittsfield State Forest

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Pittsfield State Forest holiday 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 AU$316
includes taxes & fees
8 Sept - 9 Sept
NEW RENO - Chalet-style farm loft near Tanglewood

2. 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 AU$754
includes taxes & fees
2 Sept - 3 Sept
Comfortable Berkshires retreat on mtn resort, SISO
A spacious living room with a dining area, a kitchen, and a large window.

3. 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$311
includes taxes & fees
14 Sept - 15 Sept
1800s Carriage house in Berkshires / Hudson Valley
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
9.8 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 AU$787
includes taxes & fees
2 Sept - 3 Sept
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

5. Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (77 reviews)
"Helpful host, lovely condo. Great location. Clean, tons of games and movies in unit. Also plenty of coffee pods included!"
United States
Christy F.
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
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 AU$754
includes taxes & fees
9 Sept - 10 Sept
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

7. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (7 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 AU$272
includes taxes & fees
13 Sept - 14 Sept
Cozy Home in Pownal VT
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 clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is AU$767
includes taxes & fees
2 Sept - 3 Sept
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A living room with a brown leather sofa, two grey armchairs, a glass coffee table, and a wooden side table with a lamp.

9. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.6 out of 10, Exceptional, (7 reviews)
The price is AU$543
includes taxes & fees
14 Sept - 15 Sept
stylish Berkshires Retreat
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

10. 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 AU$1,544
includes taxes & fees
9 Sept - 10 Sept
Hancock Village Inn Near Jiminy Peak
A patio with a wooden table and benches, a grill, and a garden with trees and flowers.

11. NEW RENO Historic Creamery in Berkshires w/hot tub

NEW RENO Historic Creamery in Berkshires w/hot tub
New Lebanon
10.0 out of 10, Exceptional, (7 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveller
The price is AU$716
includes taxes & fees
15 Sept - 16 Sept
NEW RENO Historic Creamery in Berkshires w/hot tub
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.

12. 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 AU$509
includes taxes & fees
9 Sept - 10 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A two-story house with a front porch, a small staircase leading to the door, and a pathway flanked by bushes and a lamp post.

13. North Getaway Cottage

North Getaway Cottage
Williamstown
8.8 out of 10, Excellent, (27 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is AU$644
includes taxes & fees
1 Oct - 2 Oct
North Getaway Cottage
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

14. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AU$433
includes taxes & fees
8 Sept - 9 Sept
Cozy Riverside Berkshires Retreat
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 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 AU$437
includes taxes & fees
3 Sept - 4 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.
A camping setup with a metal chair and a table by a river in a forest.

16. 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, (13 reviews)
"This property is really nice. House is beautiful and the man cave is a nice addition. Wish we were there long enough to use it."
United States
Jen R.
The price is AU$466
includes taxes & fees
21 Sept - 22 Sept
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A kitchen with white cabinets, a wooden dining table, and pendant lights.

17. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (58 reviews)
"Lovely home with everything we needed. The beds were very comfortable!"
United States
Jennifer O.
The price is AU$654
includes taxes & fees
9 Sept - 10 Sept
A roomy remodeled retreat close to MassMoCA
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

18. 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 AU$829
includes taxes & fees
16 Sept - 17 Sept
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

19. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is AU$553
includes taxes & fees
3 Sept - 4 Sept
Home in Great Barrington
A modern, semi-circular wooden cabin with large windows, surrounded by lush greenery and trees.

20. 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 AU$691
includes taxes & fees
9 Sept - 10 Sept
Treat yourself at the stunning June Farms Wellness Huts!
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

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"Perfect stay"
Linda 1-night trip
Posted 1 hour ago
Holiday Inn Club Vacations Oak 'n Spruce Resort

Find out more about Pittsfield State Forest

Pittsfield State Forest Holiday Homes information

Number of reviews
212
Accommodation
361 Holiday Homes
Lowest Price
AU$272
Highest Price
AU$1,544

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