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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 42 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, (214)
"The cabin is quiet, tidy, and comfortable. It is within driving distance of several hiking trails and was a great place to spend a long weekend. The host was friendly and communicative, and made sure that we had everything we needed for a nice stay. "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
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, (40)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Bear Creek Cabin
Exterior

Bear Creek Cabin

9.8 out of 10, Exceptional, (29)
"Loved it, will definitely book again!"
The price is AED 1,469
AED 2,146 total
includes taxes & fees
4 May - 5 May
Bear Creek Cabin
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)
"Great property. Exactly as advertised. "
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Charming 3-bedroom Cabin for nature lovers
Interior

Charming 3-bedroom Cabin for nature lovers

The price is AED 569
AED 1,182 total
includes taxes & fees
4 May - 5 May
Charming 3-bedroom Cabin for nature lovers
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
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)
"We had an amazing time. Cottage is perfect and the host is super communicative. We will definitely be back as the cabin and the town were just perfect. "
Ideal location for summer and winter activities with plenty of outdoor space.
Martin Van Buren historical Log cabin
Private kitchen

Martin Van Buren historical Log cabin

2.0 star property
Martin Van Buren historical Log cabin
Cabin in the woods
Exterior

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
2 May - 3 May
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 cabin was pretty much all we could wish for to spend a few cozy days in the beautiful Berkshires! "
Berkshires Cabin 2 Mi to Appalachian Trail!
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)
"Lovely location, charming property, great experience"
The price is AED 771
AED 1,195 total
includes taxes & fees
5 May - 6 May
Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !
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
2 May - 3 May
Florida Mountain Log Cabin!
A-Frame Cabin w/ Furnished Deck in Becket!
Exterior

A-Frame Cabin w/ Furnished Deck in Becket!

8.4 out of 10, Very Good, (7)
"We had a wonderful stay in this adorable a frame!! Super cozy :)"
A-Frame Cabin w/ Furnished Deck in Becket!
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
Taborton Harvest Timber Trails Unique cabin experience
Exterior

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
4 May - 5 May
Taborton Harvest Timber Trails Unique cabin experience
Private Hot Tub: Hudson Valley Cabin Retreat!
Dining

Private Hot Tub: Hudson Valley Cabin Retreat!

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had an excellent stay, went skiing at Butternut, tubing at Bousquet, and celebrated New Years at the house. Tons for the kids to do, well stocked kitchen (no condiments tho so bring your own ketchup, etc). Home owner was very responsive. Would definitely book again. "
Private Hot Tub: Hudson Valley Cabin Retreat!
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)
"Great staff clean cabin warm and cozy Great value"
The price is AED 496
AED 905 total
includes taxes & fees
22 May - 23 May
TimberTown Cabin #1 at June Farms, GLAMPING at it's finest!
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
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
Modern Cabin Near Tanglewood
Property grounds

Modern Cabin Near Tanglewood

10.0 out of 10, Exceptional, (8)
"We had a great time staying in Lauren and Blake's cabin. It was very comfortable, clean and convenient and I would definitely stay there again. Thank you for being great hosts!"
Modern Cabin Near Tanglewood
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

Hancock Village Inn at Jiminy Peak
Miscellaneous

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is AED 2,017
AED 3,810 total
includes taxes & fees
5 May - 6 May
Hancock Village Inn at Jiminy Peak
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, (140)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Dancing Horse Lodge
Fridge, microwave, oven, stovetop

Dancing Horse Lodge

9.6 out of 10, Exceptional, (41)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge
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.