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Oct 24 - Oct 26
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Nov 21 - Nov 23

Cottages in Stockbridge

The Blue Elm - A Historic Berkshire Cottage
Exterior

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (10)
"Everything was great...and beautiful!"
$362 nightly
The price is $404
Sep 30 - Oct 1
Total with taxes and fees
The Blue Elm - A Historic Berkshire Cottage
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Property grounds

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

2.0 star property
9.0 out of 10, Wonderful, (4)
"Cozy, serene and bucolic waterfront hideaway within driving distance of Tanglewood, Shakespeare & Company, Jacob's Pillow and all the wonderful food and cultural Berkshire gems! Julie and Russ were amazing hosts. Great communication and wonderful restaurant and museum suggestions. Definitely planning another long weekend retreat!"
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
Property grounds

Heaven Can't Wait, On Beautiful Kinderhook Lake!!

9.8 out of 10, Exceptional, (89)
"Home our mother's 83rd birthday party cookout at the lake house with a few family members and it was a great day. Everyone loved the house. We enjoyed the stay"
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
Charming historic cottage on scenic road to Mt. Greylock
Exterior

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (115)
"What a lovely property! And Rich was just terrific!"
Charming historic cottage on scenic road to Mt. Greylock
Light-filled cottage
Exterior

Light-filled cottage

10.0 out of 10, Exceptional, (1)
"Beautiful, well-designed home deserves a 10 out of 10 for aesthetics. Very glad Jing (the host) and her family are sharing this jewel of a home with the rest of us. Jing was a quick, kind and cordial communicator. The house location was quiet and tranquil. Nearby lake was within walking distance and delightful."
Light-filled cottage
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
Outdoor dining

Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake

10.0 out of 10, Exceptional, (7)
"Very cozy, very nice views, tranquil, serene. "
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
Private Island - Largest Fresh Water Reservoir in Mass
Outdoor dining

Private Island - Largest Fresh Water Reservoir in Mass

8.8 out of 10, Excellent, (8)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Exterior

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

9.4 out of 10, Exceptional, (15)
"A short getaway with family. "
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Entire cottage in Berkshire Villiage
Exterior

Entire cottage in Berkshire Villiage

3.0 star property
9.6 out of 10, Exceptional, (7)
"The cottage was clean and as described. The street was very quiet."
Entire cottage in Berkshire Villiage
Berkshires farm, 30+ guests, 50 acres
Exterior

Berkshires farm, 30+ guests, 50 acres

2.0 star property
$1,573 nightly
The price is $1,594
Oct 1 - Oct 2
Total with taxes and fees
Berkshires farm, 30+ guests, 50 acres
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Exterior

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

10.0 out of 10, Exceptional, (7)
"A lovely cabin centrally located in the Berkshires! Had everything we needed for our stay, including air conditioning during a heat wave! "
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
A-frame Cabin w/ Furnished Deck in Becket!
House (2 Bedrooms) | Interior

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
Plan your Berkshires by the lake
Exterior

Plan your Berkshires by the lake

8.0 out of 10, Very Good, (1)
Plan your Berkshires by the lake
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Cottage (4 Bedrooms) | Front of property

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

3.0 star property
10.0 out of 10, Exceptional, (1)
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House
House (4 Bedrooms) | Interior

Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House

3.0 star property
6.0 out of 10, (1)
"The location of the house was very near for food and supplies,yet very private. The inside was very clean and well kept. We enjoyed the quietness and surrounding grounds with views of local wild life. The things that we did not like was the musty - moldy smell when we first got there. Every time you used the water it smelled. Red light on fridge for changing filter. Bought spring water to use for drinking, coffee, and cooking. All reported to host upon departure."
Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House
Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!
House (4 Bedrooms) | Interior

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

3.0 star property
Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!
Perfect Vacation Get Away - Historical New Marlborough
Exterior

Perfect Vacation Get Away - Historical New Marlborough

9.2 out of 10, Wonderful, (57)
"Had a great time. If you love to get away from the cities and relax this is it. Bring what you need as theres no stores close."
Perfect Vacation Get Away - Historical New Marlborough
Beachwood Cottage
Exterior

Beachwood Cottage

9.6 out of 10, Exceptional, (5)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
Beachwood Cottage
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Outdoor dining

Private Lake Cottage on 3 acres w/350 sq. ft. deck

10.0 out of 10, Exceptional, (1)
"We spent a lovely, relaxing weekend in this well kept and well situated property. Hoping to come back again."
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Terrace/patio

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
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

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Staff is friendly and accommodating "
Karol 1-night trip
Posted 1 day ago
Best Western Plus Berkshire Hills Inn & Suites

Find out more about Stockbridge

Find out more about Stockbridge

Stockbridge Cottages information

Number of reviews
300
Accommodation
118 Cottages
Lowest Price
$404
Highest Price
$1,594

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