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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Chatham cottages

Interior
Charming loft cottage in tranquil Germantown with WiFi, AC

Cottage in Germantown

Charming loft cottage in tranquil Germantown with WiFi, AC
10.0 out of 10, Exceptional, (8)
"Sparkling clean, lovely and cozy hideaway. We only stayed overnight, but the kitchenette would be perfect for a longer stay. Hope we can come back sometime and stay longer."
United States
Peter S.
$193 nightly
The price is $216
Jan 4 - Jan 5, 2026
Total with taxes and fees
Charming loft cottage in tranquil Germantown with WiFi, AC
Terrace/patio
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cottage in Nassau

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
10.0 out of 10, Exceptional, (2)
"Cozy home on the lake."
United States
Terry O.
$348 nightly
The price is $386
Dec 28 - Dec 29
Total with taxes and fees
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Exterior
Charming Cottage in the Heart of Catskill & Pet Friendly

Cottage in Catskill

Charming Cottage in the Heart of Catskill & Pet Friendly
10.0 out of 10, Exceptional, (18)
"We had a wonderful time at the Catskill Nook. Everything was great and the hosts were amazing. Well located, walking distance to everything and pet friendly. The flowers from our hosts were gorgeous. We had a blast. "
United States
Bernadette P.
$316 nightly
The price is $341
Dec 24 - Dec 25
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
Terrace/patio
Pet-Friendly Hudson Escape w/ Hot Tub

Cottage in Stottville

Pet-Friendly Hudson Escape w/ Hot Tub
2.0 star property
$348 nightly
The price is $353
Jan 20 - Jan 21, 2026
Total with taxes and fees
Pet-Friendly Hudson Escape w/ Hot Tub
Exterior
Berkshires farm, 30+ guests, 50 acres

Cottage in New Lebanon

Berkshires farm, 30+ guests, 50 acres
2.0 star property
$1,724 nightly
The price is $1,747
Jan 12 - Jan 13, 2026
Total with taxes and fees
Berkshires farm, 30+ guests, 50 acres
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"While waiting for our vallet car due to construction. The hotel staff were engaging and had personal conversations with us. Rooms were good and all staff treated us exceptional. Give them an atta boy on proformance"
Nathan 1-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Chatham

Chatham Cottages information

Number of reviews
24
Accommodation
120 Cottages
Lowest Price
$216
Highest Price
$1,747

Frequently asked questions

Why book your cottage in Chatham with Expedia?
Expedia has some excellent cottages in Chatham, so get ready for an unforgettable vacay 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.

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