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Chatham Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Chatham holiday rentals

Exterior

1. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (171 reviews)
"Clean, quiet and relaxing stay."
United States
Andrea
The price is S$165
includes taxes & fees
6 Sept - 7 Sept
Micosta Leisure Inn
Lobby

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,600 reviews)
"All the amenities offered are an excellent plus. Good rates for rooms. Good place to stay at, lots to do even around the area"
United States
Alex
The price is S$128
includes taxes & fees
29 Sept - 30 Sept
Vacation Village in the Berkshires
Lobby

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,114 reviews)
"Clean & comfortable stay"
United States
Robert
The price is S$143
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
Exterior

4. 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, (290 reviews)
"Loved my stay at the little cabin, will definitely be returning."
United States
Rosemary
The price is S$273
includes taxes & fees
2 Sept - 3 Sept
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Interior

5. 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 S$705
includes taxes & fees
2 Sept - 3 Sept
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Room

6. Huttopia Berkshires

Huttopia Berkshires
2.5 star property
Williamstown
9.4 out of 10, Exceptional, (16 reviews)
"Healthy food too!"
United States
GEORGINA
The price is S$138
includes taxes & fees
8 Sept - 9 Sept
Huttopia Berkshires
Outdoor dining

7. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is S$328
includes taxes & fees
3 Sept - 4 Sept
Gatherwild Ranch
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
"The entry , bar, and dining room along with the outside patio was beautifully done. It made you happy to be there as it was so welcoming. Ample parking space, great amenities, and comfy quiet room made our stay great. The only thing missing was a floor lamp in our room so we couldn’t read at night as the small lamps were dim."
Barbara 1-night trip
Posted 2 hours ago
Berkshires Untold

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 12 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.