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

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

9.6 out of 10, Exceptional, (40)
"We had a great time here and the hosts were friendly and accommodating of our request for a later checkout. Our only complaint is the 325 cleaning fee, which is excessive given how much cleaning guests are asked to do (and given that one of the bathrooms was not even perfectly clean upon arrival). We would otherwise happily consider a future stay."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Bear Creek Cabin

9.8 out of 10, Exceptional, (29)
"Enjoyed our stay"
The price is AED 1,469
AED 2,195 total
includes taxes & fees
11 Apr - 12 Apr
Bear Creek Cabin

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

Charming 3-bedroom Cabin for nature lovers

The price is AED 514
AED 1,084 total
includes taxes & fees
28 Apr - 29 Apr
Charming 3-bedroom Cabin for nature lovers

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

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.

Martin Van Buren historical Log cabin

2.0 star property
Martin Van Buren historical Log cabin

Cabin in the woods

10.0 out of 10, Exceptional, (10)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is AED 441
AED 652 total
includes taxes & fees
11 Apr - 12 Apr
Cabin in the woods

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!

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 1,256 total
includes taxes & fees
12 Apr - 13 Apr
Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !

Florida Mountain Log Cabin!

2.0 star property
The price is AED 1,451
AED 2,395 total
includes taxes & fees
11 Apr - 12 Apr
Florida Mountain Log Cabin!

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!

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

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

Taborton Harvest Timber Trails Unique cabin experience

10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
The price is AED 441
AED 652 total
includes taxes & fees
11 Apr - 12 Apr
Taborton Harvest Timber Trails Unique cabin experience

Private Hot Tub: Hudson Valley Cabin Retreat!

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: Hudson Valley Cabin Retreat!

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 844 total
includes taxes & fees
13 Apr - 14 Apr
TimberTown Cabin #1 at June Farms, GLAMPING at it's finest!

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

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

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

Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum

9.8 out of 10, Exceptional, (56)
"Needed some time away back in New England and this was the perfect spot. Very comfortable, quiet and clean. Within a mixed vacation home residential area on a lake it was very quiet in the fall, but likely more bustling in the summer, but it is in a lake community. Nice, well built log cabin, clean and maintained. The owner communicated everything well and is easy to contact. The cabin are very close to Hinsdale and Dalton which has more amenities. Many state parks, woods and conservation lands...
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
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

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

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 3,801 total
includes taxes & fees
11 Apr - 12 Apr
Hancock Village Inn at Jiminy Peak

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.