Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Chatham vacation rentals

Exterior

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (10 reviews)
"Healthy food too!"
United States
GEORGINA
The price is P8,925
P9,970 total
includes taxes & fees
Mar 29 - Mar 30
Huttopia Berkshires
View from property

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
Catskill
9.6 out of 10, Exceptional, (183 reviews)
"We had the best time! "
United States
Eric
The price is P8,354
P11,619 total
includes taxes & fees
Mar 31 - Apr 1
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Exterior

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,317 reviews)
"Clean rooms, and very friendly staff"
United States
Amr
The price is P5,814
P7,155 total
includes taxes & fees
Mar 29 - Mar 30
Vacation Village in the Berkshires
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.4 out of 10, Exceptional, (141 reviews)
"Steven is the most helpful and kind host I've ever experienced! The property is lovely, and the rooms are cozy. I would definitely recommend staying here especially as a solo traveler."
United States
Salvio
The price is P7,810
P8,748 total
includes taxes & fees
Mar 28 - Mar 29
Micosta Leisure Inn
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
"Berkshires Untold is an old roadside motel that has been very spiffed up. The rooms are small but clean, comfortable, and nicely decorated and updated. Our bed was comfy with high end linens and a nice updated bathroom. The major drawback to the room is the very noisy HVAC unit. There's a super cozy, attractive lounge area and a charming little restaurant and bar. The menu is small but the food is quite good and having an onsite restaurant is convenient. The price we paid for a very off season Saturday night was excellent, but the rates really jack up during the summer Tanglewood season, far beyond what one would expect for a small motel room. The staff is friendly and professional, and dogs are welcome for an $85 fee. All in all, this is a very nice and sometimes very affordable Berkshires option. "
Nancy 1-night trip
Posted 4 hours ago
Berkshires Untold

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:

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

Frequently asked questions

Are there vacation rentals in Chatham?

Yes, we have vacation rentals close to top points of interest in Chatham, or you can go with a secluded option if you want a relaxing place to stay. Chatham is known for its theaters and restaurants.

How many vacation rentals are there in Chatham?

With 14 Expedia vacation rentals, you're sure 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 Kinderhook Lake. The Mac-Haydn Theatre and Martin Van Buren National Historic Site are a couple of places you'll find in the larger area.

What are vacation rentals like in Chatham?

Vacation rentals are privately owned properties you can stay in for several days or more in Chatham. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family getaway.