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Find holiday rentals that suit your style

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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 white cabinetry, granite countertops, and a window with blinds.

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, (16 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
The price is AU$353
includes taxes & fees
17 Nov - 18 Nov
Charming loft cottage in tranquil Germantown with WiFi, AC
A cabin with a wooden deck, a covered porch, and a gravel driveway.

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 AU$856
includes taxes & fees
10 Nov - 11 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 AU$489
includes taxes & fees
10 Nov - 11 Nov
Charming Cottage in the Heart of Catskill & Pet Friendly
A two-story house with a balcony, a chimney, and a window with a view.

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 AU$2,661
includes taxes & fees
1 Dec - 2 Dec
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".

Top reviews in Chatham

A wooden deck with two chairs and a table, overlooking a lush green landscape and a golf course.
Micosta Leisure Inn

Micosta Leisure Inn

Micosta Leisure Inn
Hudson

8/10 Good

Great spot, close to Hudson and the Catskills. Room was a good size with a small kitchen and veranda to sit and have a drink. Steve was a great host and cooked us a great dinner in their small restaurant.
Australia
David
Reviewed September 10, 2023
Micosta Leisure Inn

Frequently Asked Questions

What is there to do in Chatham near my cottage?

You'll find plenty of awesome things to sink your teeth into in Chatham. Check out leading attractions like The Mac-Haydn Theatre, Hudson Chatham Winery and Shaker Museum and Library. Kinderhook Lake, Van Alen House and High Falls Trail are also on many to-do lists.