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Chatham Vacation Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sep - 20 Sep
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Chatham vacation rentals

Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (159 reviews)
"This inn with cabins is a gorgeous setting with a nice vegetable garden, the setting is a bit remote and we like it, very quiet, unfortunately the restaurant was close."
United States
philippe
The price is AED 490
AED 549 total
includes taxes & fees
27 Jul - 28 Jul
Micosta Leisure Inn
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,464 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
The price is AED 437
AED 528 total
includes taxes & fees
23 Jul - 24 Jul
Vacation Village in the Berkshires
Exterior

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, (259 reviews)
"The experience was wonderful. Great and peaceful place."
United States
Seung Jae
The price is AED 731
AED 948 total
includes taxes & fees
29 Jul - 30 Jul
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,018 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is AED 460
AED 596 total
includes taxes & fees
19 Aug - 20 Aug
Berkshire Mountain Lodge
House (3 Bedrooms) | Front of property

Sleepy Hollow Lake Home w/ Deck, Pool Access!

Sleepy Hollow Lake Home w/ Deck, Pool Access!
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (2 reviews)
"The house was convenient to our friend’s wedding venue. It was spacious, clean and comfortable! There were many great amenities that we didn’t have time use due to our schedule and rainy weather."
United States
audrey
The price is AED 1,113
AED 2,173 total
includes taxes & fees
27 Jul - 28 Jul
Sleepy Hollow Lake Home w/ Deck, Pool Access!
Family Bungalow

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.2 out of 10, Wonderful, (12 reviews)
"Healthy food too!"
United States
GEORGINA
The price is AED 564
AED 630 total
includes taxes & fees
30 Jul - 31 Jul
Huttopia Berkshires
House (4 Bedrooms) | Interior

Mtn-view Retreat in Huson Valley: Great for Groups

Mtn-view Retreat in Huson Valley: Great for Groups
3.0 star property
Hudson
The price is AED 878
AED 2,719 total
includes taxes & fees
23 Jul - 24 Jul
Mtn-view Retreat in Huson Valley: Great for Groups
House (3 Bedrooms) | Interior

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 AED 823
AED 2,035 total
includes taxes & fees
26 Jul - 27 Jul
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"The king deluxe suite was large enough for a family. The kitchen was sufficiently equipped to cook meals. The in room jacuzzi was comfortable for two. The outdoor pool was large and there were plenty of lounge chairs for the guests. The indoor pool was large as well, though a bit noisy. The views were very nice and the location is relatively close to Williams town, Pittsfield and Lenox. Lots of museums and other sights in the area. Overall a very nice location for long weekend or a full week."
Sharon 2-night trip
Posted 12 hours ago
Vacation Village in the Berkshires

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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.

What are some of the best vacation home rentals that Chatham has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental near Chatham is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Chatham?

With 12 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 Hudson Chatham Winery 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.