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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Chatham holiday rentals

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

1. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (193 reviews)
"Great stay"
United States
George
The price is ฿3,329
฿3,728 total
includes taxes & fees
1 Nov - 2 Nov
Micosta Leisure Inn
Exterior

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,244 reviews)
"beautiful location, giant suite room for incredible value"
United States
Michael
The price is ฿2,789
฿3,868 total
includes taxes & fees
8 Nov - 9 Nov
Berkshire Mountain Lodge
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

3. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (331 reviews)
"Nice little cabin, well situated to sightseeing"
United States
Darryl
The price is ฿5,429
฿7,320 total
includes taxes & fees
29 Nov - 30 Nov
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

4. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,805 reviews)
"Great resort, great location very spacious."
United States
Marcos
The price is ฿2,709
฿3,396 total
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
A small wooden cabin with a bed inside, situated in a forest.

5. Gather Greene

Gather Greene
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (5 reviews)
"The room was spotless and very cozy! Everything was perfect, the scenery the smell, the atmosphere…EVRYTHING! The staff on the property were extremely friendly and generously helpful! Would 100% recommend for a couple’s getaway! Parking wasn’t a problem at all as well! Short walking distance to the cabins and back."
United States
Jabari
The price is ฿9,239
฿9,978 total
includes taxes & fees
20 Nov - 21 Nov
Gather Greene
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 Whitlock

The Whitlock

10/10 Excellent
"My son and I stayed one night at The Whitlock Inn. We booked a living area which gave my teen his privacy and extra space mine as well. It’s centrally located in the cute town of Lenox. We dined in town at a wonderful restaurant down from our Inn. The Inn had a bon fire lit to enjoy. We would stay again. Great for families or traveling with your partner.."
Maryeliza 1-night trip
Posted 3 hours ago
The Whitlock

Find out more about Chatham

Search for holiday rentals in Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in Chatham using one of the methods below:

  • View our selection of featured holiday rentals in Chatham
  • Use the map to find apartments and other holiday homes in the Chatham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chatham while they last

Look no further and take a look at our great range of rental properties in Chatham!

Frequently asked questions

Are there holiday rentals in Chatham?

Yes, there are holiday rentals close to the most popular sights in Chatham, or you can select a more secluded option if you're looking for a relaxing stay. Chatham is known for its theatres and restaurants.

How many holiday rentals are there in Chatham?

With 11 Expedia holiday rentals, you're guaranteed to find just the right place for your Chatham stay.

What can I see and do in Chatham?

While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Art Omi International Arts Center - Fields Sculpture Park. The Mac-Haydn Theatre and Martin Van Buren National Historic Site are a couple of places you'll find in the wider area.

What are holiday rentals like in Chatham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chatham. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for families.