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Next weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Hancock Cottages

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Relax on a deck overlooking a serene body of water surrounded by lush greenery and trees.

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, (84)
"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
Cozy home surrounded by lush vegetation.

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (111)
"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"
Charming historic cottage on scenic road to Mt. Greylock
Lake Views & Dock Access - Pittsfield Cottage!
Traditional homes line the quiet street, each with a central chimney and green shutters.

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (4)
"We stayed with family and friends and loved all of the offerings from the dock, fire pit and quiet neighborhood."
Lake Views & Dock Access - Pittsfield Cottage!
Beachwood Cottage
Stroll through the serene garden, surrounded by lush trees and shrubs, and discover a tranquil atmosphere perfect for relaxation.

Beachwood Cottage

10.0 out of 10, Exceptional, (4)
"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
Entire cottage in Berkshire Villiage
Situated in a wooded area, this charming house features a gabled roof and a welcoming front porch.

Entire cottage in Berkshire Villiage

3.0 star property
9.6 out of 10, Exceptional, (5)
"The cottage was clean and as described. The street was very quiet."
Entire cottage in Berkshire Villiage
Cozy cottage with pool, walking distance to lake
Relax on the front porch with a comfortable seating area.

Cozy cottage with pool, walking distance to lake

10.0 out of 10, Exceptional, (15)
"The house was very convenient to anywhere we wanted to go. We even had 5 deer welcome us the first night. House was very comfortable and we loved it."
Cozy cottage with pool, walking distance to lake
Grandparent’s Cottage 250 steps to the lake
Sun loungers, beach towels

Grandparent’s Cottage 250 steps to the lake

Grandparent’s Cottage 250 steps to the lake
Charlemont Retreat on Chickley River w/ EV Charger
Situated in a wooded area, this charming home offers a front porch with outdoor seating and a chimney.

Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Situated in a grassy area, this cozy home features a red-framed door and windows with string lights.

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

10.0 out of 10, Exceptional, (5)
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Berkshires farm, 30+ guests, 50 acres
Situated on a grassy area, this charming home features a traditional two-story design with a prominent porch and a small attached structure.

Berkshires farm, 30+ guests, 50 acres

2.0 star property
The price is CA $1,618
CA $2,639 total
includes taxes & fees
Sep 2 - Sep 3
Berkshires farm, 30+ guests, 50 acres
Spacious Historic Home in the Berkshires!
House (5 Bedrooms) | Interior

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Luxury Vacation Rental in the Berkshires!
Relax in a serene outdoor setting with a central fire pit surrounded by Adirondack chairs.

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Relax on the deck with a view of the surrounding forest, featuring a comfortable seating area with sofas and a chair.

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

10.0 out of 10, Exceptional, (3)
"We were there for 2 nights for visiting day at a camp in the Berkshires. The home is very comfortable and clean. We enjoyed our stay! "
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
House (1 Bedroom) | Front of property

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

3.0 star property
6.0 out of 10, (1)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy
Relax on the deck with comfortable seating and a decorative rug.

Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy

10.0 out of 10, Exceptional, (11)
"Our family rented this property for a long weekend trip and had a great experience. We enjoyed the beauty of the local area, including some great local restaurants and coffee shops. We were snowed in for one day of our trip and enjoyed the coziness of the property and the full kitchen came in clutch to avoid needing to travel during the storm. "
Lake Cottage - 15 Minutes to Jiminy Peak Ski Resort, Albany, Troy
Expansive Upstate Home w/ Home Theater!
House (5 Bedrooms) | Interior

Expansive Upstate Home w/ Home Theater!

3.0 star property
Expansive Upstate Home w/ Home Theater!
Picturesque Cottage with Sunroom on Ashmere Lake!
Relax on the lakeside deck with a table and chairs, surrounded by a grassy area and offering unobstructed views of the lake.

Picturesque Cottage with Sunroom on Ashmere Lake!

9.6 out of 10, Exceptional, (24)
"Beautiful lake house and ideal for our group of 4 women celebrating our 45th high school reunion. Beautiful lake view and Love that Ozzie’s is just a few miles away. "
Picturesque Cottage with Sunroom on Ashmere Lake!
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Relax in a serene garden setting surrounded by mature trees and lush greenery, with a stone fire pit and Adirondack chairs.

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
House (4 Bedrooms) | Interior

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3.0 star property
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
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 Hancock Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Studio was nice and spacious. I got there late and left early so didn’t take advantage of amenities but they looked nice."
Mitchell 1-night trip
Posted 8 hours ago
Vacation Village in the Berkshires