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

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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
$361 nightly
The price is $404
Oct 13 - Oct 14
Total with taxes and fees
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Exterior

2. 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, (26 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.
$304 nightly
The price is $340
Sep 18 - Sep 19
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
Interior

3. 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, (14 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
$235 nightly
The price is $263
Sep 23 - Sep 24
Total with taxes and fees
Charming loft cottage in tranquil Germantown with WiFi, AC
House (3 Bedrooms) | Interior

4. 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
Sep 21 - Sep 22
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

5. Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
$1,869 nightly
The price is $1,886
Oct 7 - Oct 8
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Liked everything! Mostly, the people. The staff was friendly and excited to serve us"
John 1-night trip
Posted 13 hours ago
Berkshires Untold

Find out more about Chatham

Chatham Cottages information

Number of reviews
40
Accommodation
121 Cottages
Lowest Price
$263
Highest Price
$1,886

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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