A city street with buildings, parked cars, and solar panels.

Chatham Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Chatham vacation rentals

A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

1. BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is SAR 1,010
SAR 1,287 total
includes taxes & fees
6 Oct - 7 Oct
BLUSH: Boutique TINY home*private spa*walk to town
A camping setup with a metal chair and a table by a river in a forest.

2. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (15 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is SAR 751
SAR 1,283 total
includes taxes & fees
1 Oct - 2 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A wooden interior with a dining table, chairs, and a window with a view of greenery outside.

3. Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (4 reviews)
"This place was better than the photos. Everything was well planned out and extremely comfortable. The host was very attentive with great information about the area. Would definitely recommend."
United States
Lori S.
The price is SAR 973
SAR 1,237 total
includes taxes & fees
1 Oct - 2 Oct
Sugar Shack - 300 square feet of pure sweetness.
A modern building with a wooden deck and a door.

4. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is SAR 965
SAR 2,288 total
includes taxes & fees
5 Oct - 6 Oct
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

5. 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 SAR 371
SAR 415 total
includes taxes & fees
1 Oct - 2 Oct
Micosta Leisure Inn
A wooden deck with a staircase leading to a covered porch area.

6. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (63 reviews)
"The room was sufficient to our needs. Didn’t realize it was a multi-unit property or that it was on the second floor."
United States
Douglas
The price is SAR 368
SAR 497 total
includes taxes & fees
13 Oct - 14 Oct
All comforts of home
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,163 reviews)
"Absolutely wonderful room with many amenities with short drive to Tanglewood and restaurant options."
United States
Jay
The price is SAR 299
SAR 418 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
A wooden deck with a staircase leading to a covered porch area.

8. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (37 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is SAR 399
SAR 531 total
includes taxes & fees
8 Oct - 9 Oct
All the comforts of home
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

9. 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, (313 reviews)
"Excellent place"
United States
Yeudin
The price is SAR 605
SAR 815 total
includes taxes & fees
29 Oct - 30 Oct
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A backyard with a fire pit, wooden deck, and string lights.

10. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (4 reviews)
"Enjoyed our 2 night stay, everything was clean and worked smoothly. The hot tub and couch were the favorites, also enjoyed the coffee maker very much. Would highly recommended staying here!"
United States
Ross O.
The price is SAR 702
SAR 1,362 total
includes taxes & fees
13 Oct - 14 Oct
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

11. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is SAR 263
SAR 777 total
includes taxes & fees
1 Oct - 2 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
A poolside dining area with a table set for a meal, surrounded by a pool and greenery.

12. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.2 out of 10, Wonderful, (5 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is SAR 747
SAR 1,430 total
includes taxes & fees
12 Oct - 13 Oct
Hudson NY’S Country Serenity Guest Suite.
A spacious living room with a dining area, a kitchen, and a large window.

13. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is SAR 338
SAR 860 total
includes taxes & fees
28 Oct - 29 Oct
1800s Carriage house in Berkshires / Hudson Valley
A modern interior with a staircase, wooden flooring, a dining area, and a brick wall.

14. Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (31 reviews)
"Great little place to stay at right in downtown!!"
United States
Bryan S.
Catskill Cottage Walk to Downtown & River Views
A hot tub under a wooden pergola with a natural, wooded backdrop.

15. Pet Friendly Glamping • Hot Tub • Fire Pit • Patio

Pet Friendly Glamping • Hot Tub • Fire Pit • Patio
Ravena
8.0 out of 10, Very good, (2 reviews)
"The host was very friendly. We had a great time."
United States
Richard H.
The price is SAR 406
SAR 835 total
includes taxes & fees
26 Oct - 27 Oct
Pet Friendly Glamping • Hot Tub • Fire Pit • Patio
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

16. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is SAR 338
SAR 524 total
includes taxes & fees
11 Oct - 12 Oct
Cozy 1-bedroom studio in serene Great Barrington with AC
A dining area with a table set for two, a vase with flowers, and a bottle of wine.

17. Charming Yacht on Catskill Creek

Charming Yacht on Catskill Creek
Catskill
9.2 out of 10, Wonderful, (17 reviews)
"Melissa was very welcoming and attentive during my stay. The boat was lovely and well maintained."
United States
Marcello C.
The price is SAR 490
SAR 978 total
includes taxes & fees
13 Oct - 14 Oct
Charming Yacht on Catskill Creek
A wooden cabin with a porch, a grill, and a flower planter.

18. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
The price is SAR 751
SAR 1,426 total
includes taxes & fees
1 Oct - 2 Oct
Ideal location for summer and winter activities with plenty of outdoor space.
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

19. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is SAR 563
SAR 715 total
includes taxes & fees
1 Oct - 2 Oct
The Brooks Motel: Exceptional Suite
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

20. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,689 reviews)
"Love this place for a weekend getaway."
United States
Jacob
The price is SAR 366
SAR 450 total
includes taxes & fees
20 Oct - 21 Oct
Vacation Village in the Berkshires
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

8/10 Good
"All was good for the price. Great location. Gentlemen at the bar and check-in was very pleasant and helpful. Dinner could have been better prepared."
Dan 1-night trip
Posted 1 hour ago
Berkshires Untold

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?

Catskill Cottage Walk to Downtown & River Views: This vacation home rental near Chatham offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.