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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chatham vacation rentals

A wooden structure with a neon sign reading "Sugar Shack."

1. 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 AED 951
AED 1,160 total
includes taxes & fees
16 Nov - 17 Nov
Sugar Shack - 300 square feet of pure sweetness.
A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

2. 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, (8 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 AED 951
AED 1,160 total
includes taxes & fees
16 Nov - 17 Nov
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.

3. 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, (18 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 AED 735
AED 1,197 total
includes taxes & fees
15 Nov - 16 Nov
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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 AED 951
AED 2,143 total
includes taxes & fees
16 Nov - 17 Nov
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, (197 reviews)
"Great stay"
United States
George
The price is AED 303
AED 339 total
includes taxes & fees
19 Nov - 20 Nov
Micosta Leisure Inn
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

6. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,270 reviews)
"Excellent stay!!!!"
United States
Susan J
The price is AED 282
AED 397 total
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
A wooden deck with a staircase leading to a covered porch area.

7. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (65 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 AED 360
AED 453 total
includes taxes & fees
16 Nov - 17 Nov
All comforts of home
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, (38 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is AED 390
AED 486 total
includes taxes & fees
16 Nov - 17 Nov
All the comforts of home
Indoor pool

9. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,846 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
United States
Carol
The price is AED 295
AED 370 total
includes taxes & fees
15 Nov - 16 Nov
Vacation Village in the Berkshires
A cabin with a fire pit, picnic table, and Adirondack chairs in a forest setting.

10. 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, (346 reviews)
"Everything was perfect nice and quiet and peaceful the stay there was amazing highly recommend if you want some alone time from the world🙏"
United States
Mike
The price is AED 558
AED 762 total
includes taxes & fees
14 Dec - 15 Dec
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
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
8.8 out of 10, Excellent, (8 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is AED 257
AED 711 total
includes taxes & fees
23 Nov - 24 Nov
NEW RENO - Chalet-style farm loft near Tanglewood
A gazebo with a stone floor and a grassy area with trees in the background.

12. 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 AED 441
AED 923 total
includes taxes & fees
14 Dec - 15 Dec
1800s Carriage house in Berkshires / Hudson Valley
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is AED 281
AED 425 total
includes taxes & fees
19 Nov - 20 Nov
Cozy 1-bedroom studio in serene Great Barrington with AC
A backyard with a fire pit, wooden deck, and string lights.

14. 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 AED 687
AED 1,271 total
includes taxes & fees
15 Nov - 16 Nov
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
A wooden bed in a room with a sloped ceiling and a window overlooking a forest.

15. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
10.0 out of 10, Exceptional, (1 review)
"The cabin was just what we needed! A gorgeous fall day, trees only visible from the window. The cabin had a comfortable bed, plenty of blanket and a chair. A rocker was on the porch. From this cabin, you turn right from the door and walk straight to the Bessie Woods trail. The common area had everything we needed, clean, comfortable. If you want to relax, this is pretty special!"
United States
Trena
The price is AED 463
AED 644 total
includes taxes & fees
14 Nov - 15 Nov
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
A bedroom with a large window offering a view of trees and sky.

16. 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 AED 1,005
AED 1,086 total
includes taxes & fees
4 Dec - 5 Dec
Gather Greene
A poolside dining area with a table set for a meal, surrounded by a pool and greenery.

17. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.4 out of 10, Exceptional, (6 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is AED 731
AED 1,325 total
includes taxes & fees
15 Nov - 16 Nov
Hudson NY’S Country Serenity Guest Suite.
A wooden cabin with a porch and multiple windows.

18. Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (20 reviews)
"Good location for sightseeing around the north east and New England"
United States
Nathan
The price is AED 413
AED 589 total
includes taxes & fees
14 Nov - 15 Nov
Taborton Harvest Boulder Pines Cabin in the woods
A spacious living room with wooden beams, large windows, a chandelier, and a fireplace.

19. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is AED 1,405
AED 2,335 total
includes taxes & fees
18 Nov - 19 Nov
Luxury Barn Near Hudson With New Private Sauna
A porch with two Adirondack chairs, a welcome mat, and a door labeled "Apartment 2".

20. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (6 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is AED 303
AED 768 total
includes taxes & fees
15 Nov - 16 Nov
Berkshires Apartment at the Stephentown Hotel
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"clean room - pleasant staff"
Tina 1-night trip
Posted 1 day ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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.