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

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Chatham cottages

A kitchen with a central island, white cabinetry, a stove, and a sink. There is a staircase leading to another level.

1. 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, (17 reviews)
"Everything was just right - spotless, comfortable, and easy. Thank you for a great stay!"
United States
Barbara N.
$217 nightly
The price is $243
Nov 16 - Nov 17
Total with taxes and fees
Charming loft cottage in tranquil Germantown with WiFi, AC
A wooden deck with a glass table and chairs, an umbrella, and a view of autumn trees.

2. 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
$529 nightly
The price is $587
Nov 15 - Nov 16
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A single-story house with a black front door, two windows on either side, and two black trash bins in front.

3. 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, (31 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.
$315 nightly
The price is $353
Nov 15 - Nov 16
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
A white single-story house with a front porch, surrounded by trees with autumn foliage.

4. Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
$1,802 nightly
The price is $1,819
Nov 16 - Nov 17
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

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"Convenient location. 24 hour front desk"
David 1-night trip
Posted 2 hours ago
Quality Inn Great Barrington

Find out more about Chatham

Chatham Cottages information

Number of reviews
17
Accommodation
121 Cottages
Lowest Price
$243
Highest Price
$1,819

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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