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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Pittsfield State Forest holiday rentals

Indoor pool

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,837 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
United States
Carol
The price is £75
includes taxes & fees
9 Nov - 10 Nov
Vacation Village in the Berkshires
Exterior

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,260 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is £81
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

3. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (19 reviews)
"It's super well located, with a view of the hills from the picture window. Everything is comfortable, everything worked, and host's communication was excellent. Highly recommended."
United States
David
The price is £161
includes taxes & fees
9 Nov - 10 Nov
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

4. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is £161
includes taxes & fees
9 Nov - 10 Nov
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A row of multi-story buildings with a uniform architectural style, likely a hotel or resort, set against a backdrop of green hills and trees.

5. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"Great place, everything was so easy!!"
United States
Dana
The price is £161
includes taxes & fees
9 Nov - 10 Nov
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

6. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Hancock
9.6 out of 10, Exceptional, (33 reviews)
"The suite was a great. Comfortable, clean and decorated very nicely. Bed was very comfortable with nice linens and pillows. "
United States
Eileen O.
The price is £161
includes taxes & fees
9 Nov - 10 Nov
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
A cozy living room with a large window, wooden walls, and a television.

7. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is £161
includes taxes & fees
9 Nov - 10 Nov
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Pool

8. 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 £384
includes taxes & fees
9 Nov - 10 Nov
Comfortable Berkshires retreat on mtn resort, SISO
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

9. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock
9.6 out of 10, Exceptional, (35 reviews)
"We really enjoyed our stay it was a very nice place for a family."
United States
Shmaya G.
The price is £223
includes taxes & fees
9 Nov - 10 Nov
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
A cozy living room with a fireplace, leather sofa, and a television.

10. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
The price is £161
includes taxes & fees
9 Nov - 10 Nov
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A hot tub with a wooden deck and chairs, a white building with windows, and a clear sky.

11. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (41 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is £303
includes taxes & fees
10 Nov - 11 Nov
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A wooden deck with outdoor furniture, a glass door leading to a view of a grassy area with trees.

12. Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Hancock
8.0 out of 10, Very good, (1 review)
"I chose this place at the very last minute. It was all that I expected and wanted and more: two bedrooms with three beds, a comfortable living space, two full bathrooms, kitchen with all the basic necessities, TV in each bedroom and in the living room, a dining table and chairs, an outside porch with table, a big open space, and grill, easy parking and access, quiet, .and access to two pools. The place was well tended: clean, with towels and extras blankets ready. Howard, the owner, checked on...
United States
Cecilia S.
The price is £226
includes taxes & fees
11 Nov - 12 Nov
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
A bedroom with a Minecraft-themed bedspread, pillows, and wall decor.

13. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (9 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
The price is £161
includes taxes & fees
9 Nov - 10 Nov
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
A bedroom with a large bed, two bedside tables, a painting, and a clock on the wall.

14. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is £161
includes taxes & fees
9 Nov - 10 Nov
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

15. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (35 reviews)
"Very smooth process for check in and directions. Well provisioned, super clean rooms. Really enjoyed learning about Dalton. And so many sights nearby we love!"
United States
Marcia O.
The price is £227
includes taxes & fees
10 Nov - 11 Nov
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A bedroom with a sloped ceiling, wooden beams, a bed, a window, and a chair.

16. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
10.0 out of 10, Exceptional, (1 review)
"The cabin was just what we needed! A gorgeous fall day, trees only visible from the window. The cabin had a comfortable bed, plenty of blanket and a chair. A rocker was on the porch. From this cabin, you turn right from the door and walk straight to the Bessie Woods trail. The common area had everything we needed, clean, comfortable. If you want to relax, this is pretty special!"
United States
Trena
The price is £133
includes taxes & fees
9 Nov - 10 Nov
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

17. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is £161
includes taxes & fees
9 Nov - 10 Nov
Berkshires Apartment at the Stephentown Hotel
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

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

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.8 out of 10, Excellent, (8 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 £151
includes taxes & fees
9 Nov - 10 Nov
NEW RENO - Chalet-style farm loft near Tanglewood
A swimming pool with a deck, a covered seating area, and a view of a green house and forested hills.

19. Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- Home Away From Home

Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- Home Away From Home
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"Great stay. Thank you for being a great host. "
United States
Rony N.
The price is £161
includes taxes & fees
9 Nov - 10 Nov
Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- Home Away From Home
A white two-story house with a porch, surrounded by trees and a hill.

20. 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 £296
includes taxes & fees
9 Nov - 10 Nov
1789 Shaker Farmhouse in Berkshires/Hudson Valley
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

Two Adirondack chairs facing a river with a forested hill in the background.
The Yankee Inn

The Yankee Inn

The Yankee Inn
Lenox

10/10 Excellent

Excellent room. All very clean.
United Kingdom
Martin
Reviewed October 15, 2025
The Yankee Inn

Find out more about Pittsfield State Forest

Everything you need to know about Pittsfield State Forest holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pittsfield State Forest holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pittsfield State Forest holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Pittsfield State Forest holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pittsfield State Forest. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pittsfield State Forest holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pittsfield State Forest holiday rentals we have selected for you start as low as £75 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pittsfield State Forest rentals

At Expedia, we put the best Pittsfield State Forest holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pittsfield State Forest rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pittsfield State Forest holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pittsfield State Forest. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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