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Find holiday rentals that suit your style

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Cabins
Cabins
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Apartments
Apartments

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

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.
The price is NZ$438
includes taxes & fees
16 Nov - 17 Nov
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
The price is NZ$1,063
includes taxes & fees
15 Nov - 16 Nov
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.
The price is NZ$632
includes taxes & fees
15 Nov - 16 Nov
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)
The price is NZ$3,215
includes taxes & fees
16 Nov - 17 Nov
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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Learn more about Chatham

This charming upstate village hosts the Mac-Haydn Theatre's summer productions and a vibrant Main Street with independent shops and cafés. Explore the historic Union Station or time your visit for the Columbia County Fair, a beloved local tradition since 1841.

See all hotels in Chatham
A brick building with a green dome and columns, labeled "TRACY MEMORIAL VILLAGE HALL".

Frequently Asked Questions

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.