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Compare 37 Cabin Rentals in Pittsfield with updated reviews, rates, and availability.

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (210)
"This adorable house surrounded by absolute quiet and peace, lots of woods, a trickling brook running along the property, a fire pit with wood provided. There is also pond access. It was absolutely what we needed to fully relax. The master bed was so comfortable! We loved every minute of it and I didn’t want to leave. I am certain we will be back again! There is a general store very close by that has excellent food and the owners were so friendly. They showed us around their farm. We highly...
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

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

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 SAR 450
SAR 636 total
includes taxes & fees
24 Feb - 25 Feb
Cabin in the woods

Bear Creek Cabin

9.8 out of 10, Exceptional, (25)
"Loved it, will definitely book again!"
The price is SAR 1,500
SAR 2,233 total
includes taxes & fees
26 Feb - 27 Feb
Bear Creek Cabin

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!

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 SAR 450
SAR 636 total
includes taxes & fees
24 Feb - 25 Feb
Taborton Harvest Timber Trails Unique cabin experience

Berkshires Log Cabin by Evergreen Home

10.0 out of 10, Exceptional, (7)
"We pulled in to a lighted log cabin that was lit by lights around the porch. You feel as if you are alone in the middle of the woods. It seemed all the restaurants were 20 minutes away. No shortage of good restaurants. We went to Tanglewood twice and what a treat. We saw Kool and the Gang and John Baptiste. Great performers playing in the Berkshires."
Berkshires Log Cabin by Evergreen Home

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

9.6 out of 10, Exceptional, (9)
"We stayed here for a long weekend and it’s a great house. 4 mins from butternut mountain which was perfect for us. We had a bit of a mini snowstorm while there and had a small issue getting in the driveway but when we called asking for someone to plow they showed up within minutes. Very responsive and helpful checkin and checkout as well. "
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard

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.

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

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!

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!

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 SAR 506
SAR 851 total
includes taxes & fees
24 Feb - 25 Feb
TimberTown Cabin #1 at June Farms, GLAMPING at it's finest!

Cozy 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 SAR 750
SAR 1,151 total
includes taxes & fees
1 Mar - 2 Mar
Cozy Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !

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!

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

Lakeshore cabin with private beach and dock

10.0 out of 10, Exceptional, (3)
"We love this place! It is conveniently located for Tanglewood and the Rockwell museum, quiet and secluded. The cabin and grounds show much care and attention by thoughtful owners. "
Lakeshore cabin with private beach and dock

TimberTown Cabin #3 at June Farms, GLAMPING at it's finest!

10.0 out of 10, Exceptional, (1)
"June Farms is amazing!!! The property was so fun to explore, and the staff were friendly and accommodating. We 100% recommend. I would go back again and again!"
The price is SAR 506
SAR 839 total
includes taxes & fees
24 Feb - 25 Feb
TimberTown Cabin #3 at June Farms, GLAMPING at it's finest!

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
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

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (55)
"Perfect lake front home to get away for a quick weekend trip with the family over the holidays!! Location, location location, close proximity to downtown Pittsfield, 15 from Jiminy peak & Bousquet Mt. Andrey was extremely helpful throughout the process with suggestions for food and activities for the kids. The house was a perfect fit for our family and friends. Everyone enjoyed their time there and would definitely book again"
Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (9)
"Annual mother/son ski and food fest!Lots of fun with family and friends. Plenty of space for everyone.. Kitchen wascwell"
The price is SAR 2,243
SAR 3,980 total
includes taxes & fees
25 Feb - 26 Feb
Hancock Village Inn at 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.