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Aug 15 - Aug 17
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Cabin Rentals in Stockbridge

Newly Renovated Cabin in the Country
Surrounded by lush greenery, this cabin-style building features a charming front porch and a stone chimney.

Newly Renovated Cabin in the Country

10.0 out of 10, Exceptional, (30)
"Very comfortable place with everything we needed for great week!"
Newly Renovated Cabin in the Country
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Situated in a wooded area, this charming house features a front porch and a small garden with plants and a decorative pumpkin.

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

9.8 out of 10, Exceptional, (29)
"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
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Surrounded by lush trees, this cabin features a spacious porch and a covered area with multiple windows.

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (217)
"Cabin was exactly what we were looking for in a weekend away. Great location, quiet, and had everything we needed. Hope to go back again soon! "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Artist's Camp on Lake Mahkeenac
Enjoy serene lakeside views and peaceful surroundings, perfect for picnics and outdoor activities.

Artist's Camp on Lake Mahkeenac

9.6 out of 10, Exceptional, (19)
"Great location, comfortable, beautiful setting and nice porch! "
Artist's Camp on Lake Mahkeenac
Dadzpad Cabin in Stephentown
Kitchen with central island, stove, microwave, and sink, featuring a window and patterned tile floor.

Dadzpad Cabin in Stephentown

5.0 out of 10, (2)
"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
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
Stylish log cabin with a central entrance and two windows on each side, set amidst a well-manicured lawn.

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

9.8 out of 10, Exceptional, (57)
"Great cabin on a beautiful lake. Scenic drive to all other attractions in the Berkshires (Lenox, Mt. Greylock, etc.). We enjoyed our stay!"
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
'The Mill River Cabin’ w/ Fireplace & River View!
Cozy space with a high ceiling, large windows, and a central wooden table.

'The Mill River Cabin’ w/ Fireplace & River View!

9.8 out of 10, Exceptional, (41)
"We had a great time during our stay at the Mill Creek cabin! The views of the river couldn't be beat & we enjoyed spending time reading on the porch & watching the wildlife from the huge living room windows. We will definitely be back!"
'The Mill River Cabin’ w/ Fireplace & River View!
Ideal location for summer and winter activities with plenty of outdoor space.
Relax on the porch with a grill and planter, surrounded by a serene natural landscape.

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

9.8 out of 10, Exceptional, (72)
"Excellent host!"
Ideal location for summer and winter activities with plenty of outdoor space.
Luxurious & Modern 3 BR 1.5 Bath Log Cabin
Enjoy cooking in this well-equipped kitchen with a central island, sink, and dining area.

Luxurious & Modern 3 BR 1.5 Bath Log Cabin

9.6 out of 10, Exceptional, (4)
"Spotlessly clean cabin beautifully decorated with a modern cabin vibe. 20 minutes from Great Barrington & Butternut ski area. 10 minutes to Catamount ski area. Would definitely rent again."
Luxurious & Modern 3 BR 1.5 Bath Log Cabin
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Relax in this serene room with a large bed, stone fireplace, and forest views.

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

9.6 out of 10, Exceptional, (43)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Charming 3-bedroom Cabin for nature lovers
Cozy room with a stone fireplace, flat-screen TV, and patterned rug.

Charming 3-bedroom Cabin for nature lovers

8.0 out of 10, Very Good, (1)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
$336 nightly
The price is $373
Aug 13 - Aug 14
Total includes taxes and fees
Charming 3-bedroom Cabin for nature lovers
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Relax on the spacious deck with a covered seating area, surrounded by lush greenery.

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

10.0 out of 10, Exceptional, (122)
"Had an amazing weekend in this beautiful cabin! Highly recommend staying here! Great host, amazing views, beautiful property!"
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Guesthouse Cabin vacation rentals in Berkshire County
Cozy cabin interior with a high ceiling and wooden beams, featuring a central dining table and fireplace.

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (7)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
$720 nightly
The price is $804
Aug 6 - Aug 7
Total includes taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Romantic and Secluded Berkshire's Gem
Cozy cabin-style interior with a central island kitchen, open fireplace, and comfortable seating area.

Romantic and Secluded Berkshire's Gem

9.8 out of 10, Exceptional, (14)
"My friends and I had an amazing time staying in the cozy cabin. 9 of us slept comfortably, the place was spotless, and so cute. We hope to visit again."
Romantic and Secluded Berkshire's Gem
Berkshires Cabin 2 Mi to Appalachian Trail!
Enjoy meals around a large round table in a room with a window offering a view of the surrounding forest.

Berkshires Cabin 2 Mi to Appalachian Trail!

9.8 out of 10, Exceptional, (12)
"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!
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Cozy space with a fireplace, perfect for relaxation and reading, featuring a comfortable seating area and storage shelves.

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

9.8 out of 10, Exceptional, (13)
"Very enjoyable stay, highly recommended."
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Private Hot Tub: Hudson Valley Cabin Retreat!
Enjoy a rustic retreat with a large dining table, vintage stove, and cozy fireplace.

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!
A-Frame Cabin w/ Furnished Deck in Becket!
Situated in a forested area, this cabin features a balcony for outdoor relaxation and a gravel pathway leading to the entrance.

A-Frame Cabin w/ Furnished Deck in Becket!

8.6 out of 10, Excellent, (8)
"We had a wonderful stay in this adorable a frame!! Super cozy :)"
A-Frame Cabin w/ Furnished Deck in Becket!
Luxe Log Cabin Minutes From Skiing, Hiking, & More
Cozy cabin with a large dining table and wicker chairs, offering a serene forest view.

Luxe Log Cabin Minutes From Skiing, Hiking, & More

Luxe Log Cabin Minutes From Skiing, Hiking, & More
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Relax in this inviting living area with a sofa, armchair, and coffee table, featuring a gas stove and ample natural light.

Cozy Stockbridge Cabin - Walk to Beach & Lake!

9.4 out of 10, Exceptional, (11)
"Location of this property is near all things Stockbridge has to offer. Easy ride to Tanglewood Short ride to Lenox and Lee The cottage is an older gem Well stocked and lots of quirky charm"
Cozy Stockbridge Cabin - Walk to Beach & Lake!
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 Stockbridge Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Very friendly staff. Restaurant/bar on sight very convenient."
Eithne 5-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG