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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Cottages in Old Chatham

Rose Cottage
Outdoor dining

Rose Cottage

9.6 out of 10, Exceptional, (5)
"It's so peaceful there. It was lovely."
Rose Cottage
Heaven Can't Wait, On Beautiful Kinderhook Lake! 4TH OF JULY FIREWORKS ON LAKE!
Property grounds

Heaven Can't Wait, On Beautiful Kinderhook Lake! 4TH OF JULY FIREWORKS ON LAKE!

9.8 out of 10, Exceptional, (83)
"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! 4TH OF JULY FIREWORKS ON LAKE!
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Dining

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

2.0 star property
8.0 out of 10, Very Good, (1)
"Host communicates well. Beautiful screened in porch. Furniture throughout much nicer than typical VRBO fare. Downside is that nearby freight train line is loud, and it runs regularly night and day. "
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Charming Cottage in Private Lake Community (Pet-Friendly!)
Fridge, microwave, oven, stovetop

Charming Cottage in Private Lake Community (Pet-Friendly!)

9.8 out of 10, Exceptional, (29)
"We enjoyed ourselves,relaxed,visited had a very enjoyable bisit"
Charming Cottage in Private Lake Community (Pet-Friendly!)
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Interior

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

10.0 out of 10, Exceptional, (4)
"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
Charming historic cottage on scenic road to Mt. Greylock
Outdoor dining

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (110)
"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
Near Hospitals: Home w/ Yard in Albany!
House (3 Bedrooms) | Front of property

Near Hospitals: Home w/ Yard in Albany!

3.0 star property
Near Hospitals: Home w/ Yard in Albany!
Lake Views & Dock Access - Pittsfield Cottage!
Outdoor dining

Lake Views & Dock Access - Pittsfield Cottage!

10.0 out of 10, Exceptional, (3)
"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!
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
Interior

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

10.0 out of 10, Exceptional, (6)
"Very clean, cute house right on the lake. We enjoyed our time there. "
Cozy Hudson Valley Lake Cottage :4 Kayaks + a Canoe, 400 acre Lake
Beachwood Cottage
Interior

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
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
Berkshires farm, 30+ guests, 50 acres
Exterior

Berkshires farm, 30+ guests, 50 acres

2.0 star property
The price is AED 6,244
AED 9,261 total
includes taxes & fees
13 Aug - 14 Aug
Berkshires farm, 30+ guests, 50 acres
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Charming Albany Retreat ~ 3 Mi to Downtown!
House (3 Bedrooms) | Interior

Charming Albany Retreat ~ 3 Mi to Downtown!

3.0 star property
Charming Albany Retreat ~ 3 Mi to Downtown!
Albany Home w/ Fenced Yard & Patio - Pets Welcome!
House (3 Bedrooms) | Interior

Albany Home w/ Fenced Yard & Patio - Pets Welcome!

3.0 star property
Albany Home w/ Fenced Yard & Patio - Pets Welcome!
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
Cozy cottage with pool, walking distance to lake
Outdoor pool

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
Chic Troy Home Near Downtown, 9 Mi to Albany!
House (2 Bedrooms) | Interior

Chic Troy Home Near Downtown, 9 Mi to Albany!

3.0 star property
8.0 out of 10, Very Good, (1)
Chic Troy Home Near Downtown, 9 Mi to Albany!
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Fridge, microwave, stovetop, dishwasher

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

10.0 out of 10, Exceptional, (2)
"Stayed for 3 nights over Presidents Day weekend, and we loved the spot! Recently refreshed with a new kitchen, floors and fixtures, it’s still felt warm and inviting. The electric fire / heater in the living room was well used, and we cooked our meals with the new appliances and well equipped kitchen. Proximity to Great Barrington, Stockbridge, Lenox, Lee, and all of the outdoor adventures (and shopping/restaurants) worked out perfectly, even given the snowy/ice weather. Plenty of space for the...
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Sleepy Hollow Lake Home w/ Deck, Pool Access!
House (3 Bedrooms) | Interior

Sleepy Hollow Lake Home w/ Deck, Pool Access!

3.0 star property
Sleepy Hollow Lake Home w/ Deck, Pool Access!
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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Frequently asked questions

Why book your cottage in Old Chatham with Expedia?
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