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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Pittsfield State Forest vacation homes

Exterior detail

1. White Lily Lodge 50 acre estate with private lake

White Lily Lodge 50 acre estate with private lake
Cropseyville
The price is AED 2,645
AED 4,232 total
includes taxes & fees
13 Aug - 14 Aug
White Lily Lodge 50 acre estate with private lake
Coffee/tea maker, fridge, microwave, oven

2. 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 AED 264
AED 771 total
includes taxes & fees
10 Aug - 11 Aug
NEW RENO - Chalet-style farm loft near Tanglewood
TV, DVD player, books, video library

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 AED 463
AED 1,007 total
includes taxes & fees
10 Aug - 11 Aug
1800s Carriage house in Berkshires / Hudson Valley
Coffee/tea maker, fridge, microwave, stovetop

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, (6 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is AED 646
AED 2,059 total
includes taxes & fees
9 Aug - 10 Aug
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Pool

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, (74 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.
The price is AED 1,297
AED 2,429 total
includes taxes & fees
12 Aug - 13 Aug
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
A heated pool

6. 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 AED 646
AED 2,052 total
includes taxes & fees
9 Aug - 10 Aug
Comfortable Berkshires retreat on mtn resort, SISO
Dining

7. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (6 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 AED 426
AED 757 total
includes taxes & fees
9 Aug - 10 Aug
Cozy Home in Pownal VT
Exterior

8. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (4 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 AED 992
AED 2,047 total
includes taxes & fees
1 Sep - 2 Sep
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Outdoor dining

9. 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, (9 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 1,154
AED 2,019 total
includes taxes & fees
8 Aug - 9 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Smart TV

10. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is AED 783
AED 1,659 total
includes taxes & fees
19 Aug - 20 Aug
stylish Berkshires Retreat
Interior

11. 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, (6 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 714
AED 1,602 total
includes taxes & fees
12 Aug - 13 Aug
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Coffee/tea maker, fridge, microwave, oven

12. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (36 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
Home in Great Barrington
Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 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 AED 643
AED 1,169 total
includes taxes & fees
1 Sep - 2 Sep
Sweet Cozy Victorian in Housatonic. Close to everything.
Outdoor dining

14. Ski's The Day: Winsome 3-bedroom mountain townhome with AC in Jiminy Peak

Ski's The Day: Winsome 3-bedroom mountain townhome with AC in Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"good"
United States
Ismael
Ski's The Day: Winsome 3-bedroom mountain townhome with AC in Jiminy Peak
Exterior

15. Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.

Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.
Hinsdale
10.0 out of 10, Exceptional, (9 reviews)
"Kendra was an excellent host! Very nice and welcoming and answered questions promptly. The house was beautiful and the country setting and lake was picturesque. "
United States
Joseph L.
The price is AED 1,084
AED 2,187 total
includes taxes & fees
10 Aug - 11 Aug
Hummingbird Haven is a woodland retreat surrounded by Nature and Local Charm.
Exterior

16. 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 AED 826
AED 1,740 total
includes taxes & fees
31 Aug - 1 Sep
North Getaway Cottage
Interior

17. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (21 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 AED 820
AED 1,260 total
includes taxes & fees
19 Aug - 20 Aug
Cozy Riverside Berkshires Retreat
Outdoor dining

18. 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 AED 2,696
AED 4,713 total
includes taxes & fees
10 Aug - 11 Aug
Hancock Village Inn Near Jiminy Peak
Outdoor dining

19. 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, (6 reviews)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
United States
Anonymous traveler
The price is AED 1,087
AED 2,200 total
includes taxes & fees
1 Sep - 2 Sep
NEW RENO Historic Creamery in Berkshires w/hot tub
Exterior

20. The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful cabin in a beautiful location. Host is amazing, very responsive. "
United States
Anonymous traveler
The price is AED 1,128
AED 1,832 total
includes taxes & fees
2 Sep - 3 Sep
The 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

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Jiminy Peak is located in an absolutely beatiful location in the Berkshires. And it has fun family-friendly summertime activities. But it could use some sprucing up. The pool liner is a little wrinkly and the hot tub is quite stained near the water line. In addition, our room had a nice 2-foot gouge in the wall seemingly caused by the corner of the armchair beneath it. It seems that could/should have been repaired before out arrival. And the dated counertops and fixtures are showing their age. That said, so am I! On the plus side: the iconic scenery, the friendly helpful staff, and the amenities. All in all, a good value for a family getaway. I would definitely recommend the prolerty overall."
Fausto 2-night trip
Posted less than an hour ago
Jiminy Peak Mountain Resort

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