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Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chatham vacation 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, (180 reviews)
"Great little place."
United States
Kim
The price is ₩133,833
₩149,877 total
includes taxes & fees
Oct 27 - Oct 28
Micosta Leisure Inn
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,174 reviews)
"Our visit was very nice. Facilities were beautiful!"
United States
marilyn
The price is ₩114,897
₩158,283 total
includes taxes & fees
Oct 18 - Oct 19
Berkshire Mountain Lodge
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

3. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,710 reviews)
"Very pleased with our stay -great place for the family we will G-d willing return"
United States
Denton
The price is ₩115,604
₩143,834 total
includes taxes & fees
Nov 1 - Nov 2
Vacation Village in the Berkshires
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

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, (317 reviews)
"Excellent place"
United States
Yeudin
The price is ₩215,795
₩290,963 total
includes taxes & fees
Nov 4 - Nov 5
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A cabin with a triangular window, wooden walls, and a bed with pillows.

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 ₩349,322
₩377,268 total
includes taxes & fees
Nov 1 - Nov 2
Gather Greene
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

6. 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 ₩300,236
₩742,763 total
includes taxes & fees
Oct 7 - Oct 8
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A tented area with two wooden folding chairs and a table, a patterned rug, and a view of greenery and a white tent in the background.

7. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is ₩298,561
₩364,413 total
includes taxes & fees
Oct 18 - Oct 19
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Love the fireplace in our room! The amenities always make this place worth the money, and the views to top it all off!!"
Jennifer 1-night trip
Posted 7 hours ago
Vacation Village in the Berkshires

Find out more about Chatham

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

  • View our selection of featured Vacation rentals in Chatham
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  • Enter your travel dates to view the best deals on Vacation 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 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 11 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 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 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.