A city street with buildings, parked cars, and solar panels.

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Chatham cottages

Terrace/patio

1. Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
$363 nightly
The price is $406
Aug 14 - Aug 15
Total with taxes and fees
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Property grounds

2. Pet Friendly • Fenced Yard • Hot Tub • Romantic

Pet Friendly • Fenced Yard • Hot Tub • Romantic
Ravena
10.0 out of 10, Exceptional, (1 review)
"This was a very quaint cottage type home the owner was very quick with replies. Loved that it had a fenced in yard for our dog. Was scheduled to work at the hospital all weekend, so this was a nice getaway from the hustle and bustle. We’ll stay again if we are ever in the area. "
United States
Sunshine G.
$311 nightly
The price is $336
Sep 9 - Sep 10
Total with taxes and fees
Pet Friendly • Fenced Yard • Hot Tub • Romantic
House (4 Bedrooms) | Interior

3. Mtn-view Retreat in Huson Valley: Great for Groups

Mtn-view Retreat in Huson Valley: Great for Groups
3.0 star property
Hudson
$680 nightly
The price is $762
Aug 21 - Aug 22
Total with taxes and fees
Mtn-view Retreat in Huson Valley: Great for Groups
Exterior

4. Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (24 reviews)
"Everything was great! The house is in a great location and is very clean, modern and cozy. I would highly recommend staying here! "
United States
Dave P.
$319 nightly
The price is $357
Aug 21 - Aug 22
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
Interior

5. Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC
Germantown
10.0 out of 10, Exceptional, (12 reviews)
"Very clean, comfortable, good location, great communication with host. "
United States
Lisa B.
$223 nightly
The price is $250
Sep 9 - Sep 10
Total with taxes and fees
Charming loft cottage in tranquil Germantown with WiFi, AC
Exterior

6. Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
$2,129 nightly
The price is $2,161
Sep 8 - Sep 9
Total with taxes and fees
Berkshires farm, 30+ guests, 50 acres
House (3 Bedrooms) | Front of property

7. Sleepy Hollow Lake Home w/ Deck, Pool Access!

Sleepy Hollow Lake Home w/ Deck, Pool Access!
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (2 reviews)
"The house was convenient to our friend’s wedding venue. It was spacious, clean and comfortable! There were many great amenities that we didn’t have time use due to our schedule and rainy weather."
United States
audrey
$548 nightly
The price is $591
Aug 19 - Aug 20
Total with taxes and fees
Sleepy Hollow Lake Home w/ Deck, Pool Access!
House (3 Bedrooms) | Interior

8. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
$499 nightly
The price is $554
Aug 10 - Aug 11
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"The staff were friendly, helpful with finding restaurants and other local attractions. Our room was immaculate and nicely furnished with modern furnishings in great condition. The room was quiet--we never heard our neighbors. It was pleasant to sit on the balcony and read. The location is great, 15 or 20 mins to Tanglewood depending on time. A very nice breakfast with lots of choices. We would definitely recommend this Inn to friends, and plan to return for future trips to Tanglewood and The Berkshires. ."
John 2-night trip
Posted 1 hour ago
The Yankee Inn

Find out more about Chatham

Chatham Cottages information

Number of reviews
15
Accommodation
132 Cottages
Lowest Price
$250
Highest Price
$2,161

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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