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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
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29 Aug - 31 Aug
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26 Sept - 28 Sept

Featured Cottages in Chatham

4 Mi to Dtwn Catskill: Mtn-view Home
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4 Mi to Dtwn Catskill: Mtn-view Home

3.0 star property
4 Mi to Dtwn Catskill: Mtn-view Home
Private Hot Tub: Hudson Valley Cabin Retreat!
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Private Hot Tub: Hudson Valley Cabin Retreat!

3.0 star property
Private Hot Tub: Hudson Valley Cabin Retreat!
Spacious Historic Home in the Berkshires!
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Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
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!
Expansive Upstate Home w/ Home Theater!
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Expansive Upstate Home w/ Home Theater!

3.0 star property
Expansive Upstate Home w/ Home Theater!
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!
Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay
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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 Catskills Home w/ Pond on 2 Acres!
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Cozy Catskills Home w/ Pond on 2 Acres!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Absolutely gorgeous property, the owner is awesome and can’t forget Leo the cat. "
Cozy Catskills Home w/ Pond on 2 Acres!
Sleepy Hollow Lake Home w/ Deck, Pool Access!
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Sleepy Hollow Lake Home w/ Deck, Pool Access!

3.0 star property
Sleepy Hollow Lake Home w/ Deck, Pool Access!
Modern-chic Athens Home - Fish, Ski & Swim!
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Modern-chic Athens Home - Fish, Ski & Swim!

3.0 star property
Modern-chic Athens Home - Fish, Ski & Swim!
Pet-friendly Hudson Home Near Won Dharma Center!
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Pet-friendly Hudson Home Near Won Dharma Center!

3.0 star property
Pet-friendly Hudson Home Near Won Dharma Center!
Cozy Stockbridge Cabin - Walk to Beach & Lake!
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Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
2.0 out of 10, (1)
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Whitney by Avantstay Private Berkshires Estate
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Whitney by Avantstay Private Berkshires Estate

3.0 star property
Whitney by Avantstay Private Berkshires Estate
Skiing & Hiking: Water-view Home in the Berkshires
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Skiing & Hiking: Water-view Home in the Berkshires

3.0 star property
Skiing & Hiking: Water-view Home in the Berkshires
Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!
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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!
Peaceful Athens Retreat at Sleepy Hollow Lake
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Peaceful Athens Retreat at Sleepy Hollow Lake

3.0 star property
Peaceful Athens Retreat at Sleepy Hollow Lake
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
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Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

3.0 star property
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Berkshire Hideaway w/ Fire Pit & Playground!
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Berkshire Hideaway w/ Fire Pit & Playground!

3.0 star property
Berkshire Hideaway w/ Fire Pit & Playground!
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
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Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

3.0 star property
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
Stockbridge Home: Walk to Town Beach!
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Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!
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 Chatham Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Great location to stay between Tanglewood concerts. Will come again."
Stefan 1-night trip
Posted 13 hours ago
Berkshire Mountain Lodge

Frequently asked questions

Why book your cottage in Chatham with Expedia?
Expedia has some excellent cottages in Chatham, so get ready for an unforgettable holiday on nature's doorstep. If you need to stick to a budget, choose how much you want to spend and the star rating of your property. Or, use our filters to search for cottages with a pool or free WiFi. We'll help you find the perfect place whatever your bank balance or plans.
How can I find cheap cottages in Chatham?
With Expedia's useful filter tool, scoring cheap cottages in Chatham has never been easier. To discover properties that'll make your hip pocket happy, narrow down your search by budget, star rating and amenities.
What is there to do in Chatham near my cottage?
Once you've checked in to your hotel, get out and discover the amazing things Chatham has on offer. The Mac-Haydn Theatre is a popular attraction to add to your must-see list.