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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

Compare 43 Cabin Rentals in Pittsfield with updated reviews, rates, and availability.

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Exterior

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (211)
"We loved our stay! The cabin appears to be recently renovated with modern appliances and furnishings. We got quite a bit of snow during our stay, and someone came to plow the driveway for us. A well-stocked kitchen was also helpful while we were snowed in! The cabin is close to Canterbury Farm, which we loved for cross country skiing, and close to Lee for restaurants and shopping. The host answered our questions quickly! "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Bear Creek Cabin
Exterior

Bear Creek Cabin

9.8 out of 10, Exceptional, (27)
"Perfect place to stay while skiing Berkshire East! Clean, spacious, and beautiful surroundings!"
The price is AED 1,469
AED 2,199 total
includes taxes & fees
19 Mar - 20 Mar
Bear Creek Cabin
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Charming 3-bedroom Cabin for nature lovers
Interior

Charming 3-bedroom Cabin for nature lovers

The price is AED 423
AED 916 total
includes taxes & fees
16 Apr - 17 Apr
Charming 3-bedroom Cabin for nature lovers
Modern Cabin Near Tanglewood
Property grounds

Modern Cabin Near Tanglewood

10.0 out of 10, Exceptional, (8)
"A wonderful cabin with all the amenities you will need. Clean, beautifully decorated, and so much room. Highly recommend! Will be back for sure. "
Modern Cabin Near Tanglewood
Ideal location for summer and winter activities with plenty of outdoor space.
Terrace/patio

Ideal location for summer and winter activities with plenty of outdoor space.

9.6 out of 10, Exceptional, (70)
"As is our custom we picked a place to celebrate Thanksgiving with our family. The location is usually in an area that is quiet, out in the country. This property did not disappoint us. Vivianna is a great host, always answering any questions or concerns. Great location, tucked away off the road, but close to all things one may need. Great fireplace, cozy living room dining area and bedrooms. We would recommend this property to anyone who is looking for a place to just relax and enjoy the...
Ideal location for summer and winter activities with plenty of outdoor space.
Cabin in the woods
Exterior

Cabin in the woods

10.0 out of 10, Exceptional, (9)
"This place was awesome... I was 15 minutes away working late... and I was too tired to drive home... I actually scheduled the wrong night and realized it after I got confirmation. But I messaged the renters and they just happened to have a cabin vacancy... they gave me the directions.. the key code and we worked everything out afterwards. The set-up is genius... the common area building has all the plumbing in it. Bathroom and showers with an open very well built living room with a kitchen. My...
The price is AED 441
AED 623 total
includes taxes & fees
19 Mar - 20 Mar
Cabin in the woods
Berkshires Cabin 2 Mi to Appalachian Trail!
TV, fireplace, books

Berkshires Cabin 2 Mi to Appalachian Trail!

9.8 out of 10, Exceptional, (11)
"The hosts were extremely responsive and helpful, providing us with hiking ideas, questions regarding the house and suggesting best shopping spots for incidentals. The living room was cozy, seating five comfortably. The kitchen was well stocked so cooking a Thanksgiving meal was a pleasure. We thoroughly enjoyed ourselves."
Berkshires Cabin 2 Mi to Appalachian Trail!
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Aerial view

Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard

9.8 out of 10, Exceptional, (11)
"Very enjoyable stay, highly recommended."
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

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

10.0 out of 10, Exceptional, (24)
"We had a great time in the cottage. It was perfectly cozy for our family of 6. The cottage has everything you need to have fun on a cold winter night. We especially enjoyed the hot tub and board games! Thanks for a lovely stay - we will come back in the summer!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Florida Mountain Log Cabin!
Living area

Florida Mountain Log Cabin!

2.0 star property
The price is AED 1,451
AED 2,395 total
includes taxes & fees
19 Mar - 20 Mar
Florida Mountain Log Cabin!
Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !
1 bedroom, in-room safe, WiFi, bed sheets

Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !

10.0 out of 10, Exceptional, (8)
"Kelly was a great host. Looking to come back in the summer for sure!"
The price is AED 735
AED 1,120 total
includes taxes & fees
19 Mar - 20 Mar
Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !
A-Frame Cabin w/ Furnished Deck in Becket!
Exterior

A-Frame Cabin w/ Furnished Deck in Becket!

8.4 out of 10, Very Good, (6)
"This A-frame cabin was the perfect location for some Berkshire R&R. Close to so many of western MA's greatest attractions, we had a great time visiting Tanglewood and museums, and touring local towns and restaurants. The property was clean, as described, and very comfortable. Communicating with our hosts was very simple. We will be happy to return!"
A-Frame Cabin w/ Furnished Deck in Becket!
Private Hot Tub: Spacious Austerlitz Ski Cabin!
Dining

Private Hot Tub: Spacious Austerlitz Ski Cabin!

2.0 star property
10.0 out of 10, Exceptional, (2)
"A group of 10 friends (we are in out 40's) and I stayed here for a yearly gathering that we do. Every person was amazed at the rental. It was warm, clean, inviting and the kitchen jad everything that i needed to feed 10 people over the weekend.The game room was amazing and kept the group active indoors. It had a beautiful fireplace and wood stove. The adjacent room had a dining table, another wood stove and some very thoughtful items in a welcome basket. Next to that was the kitchen/living...
Private Hot Tub: Spacious Austerlitz Ski Cabin!
Newly Renovated Cabin in the Country
Exterior

Newly Renovated Cabin in the Country

10.0 out of 10, Exceptional, (29)
"We booked this escape as a 1/2 way point between family in NJ and MA and what a hidden gem it is! Dog friendly was a priority, but the magic of this place was a welcomed surprise. All weekend we commented on wishing we stayed longer and that we must come back to really enjoy the property and cozy feel that warms the soul! The cabin is meticulously maintained and it is very clear that the family loves their home away from home! Can’t wait to return!!"
Newly Renovated Cabin in the Country
Dadzpad Cabin in Stephentown
Fridge, microwave, oven, stovetop

Dadzpad Cabin in Stephentown

8.0 out of 10, Very Good, (1)
"House was clean and comfortably furnished. The kids enjoyed the arcade games and it was an overall good time. Only Issues were that the drive and walk ways were hidden in the snow and the house did not hold heat well "
Dadzpad Cabin in Stephentown
Beautiful cabin in the woods close to skiing, hiking and shopping
Smart TV, fireplace, video games, foosball

Beautiful cabin in the woods close to skiing, hiking and shopping

Beautiful cabin in the woods close to skiing, hiking and shopping
TimberTown Cabin #1 at June Farms, GLAMPING at it's finest!
Exterior

TimberTown Cabin #1 at June Farms, GLAMPING at it's finest!

9.8 out of 10, Exceptional, (6)
"June Farms is a great place to unplug and recharge. The people there are wonderful!!!!!! We can’t wait to go back!!!!!"
The price is AED 496
AED 833 total
includes taxes & fees
19 Mar - 20 Mar
TimberTown Cabin #1 at June Farms, GLAMPING at it's finest!
Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape!
Smart TV, fireplace

Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape!

9.2 out of 10, Wonderful, (7)
"It was a beautiful property!"
Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape!
Artist's Camp on Lake Mahkeenac
Property map

Artist's Camp on Lake Mahkeenac

9.6 out of 10, Exceptional, (18)
"Great location, comfortable, beautiful setting and nice porch! "
Artist's Camp on Lake Mahkeenac
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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Other property types in Pittsfield

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (139)
"We have stayed at this property twice before and have been very pleased with the amount of bedrooms and sleeping available. The property is always very clean and is equipped with everything you need for cooking and dining.the property is a half way point for family members in several directions. "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Hancock Village Inn at Jiminy Peak
Miscellaneous

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is AED 2,016
AED 3,680 total
includes taxes & fees
21 Mar - 22 Mar
Hancock Village Inn at Jiminy Peak
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Exterior

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (56)
"Perfect location and accommodation for my family. The home was as described. I would recommend it. The property owner was easy to work with. "
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
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.