Find and Compare Chatham Condo Resort Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
apart-hotel image
Aparthotels
Aparthotels

Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3
No exact matches found, but these alternatives could be just right

Recommended hotels in Chatham

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 CA $362
CA $444 total
includes taxes & fees
Nov 17 - Nov 18
BLUSH: Boutique TINY home*private spa*walk to town
A wooden interior with a dining table, chairs, and a window with a view of greenery outside.

2. 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 CA $363
CA $446 total
includes taxes & fees
Nov 16 - Nov 17
Sugar Shack - 300 square feet of pure sweetness.
Exterior

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, (16 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 CA $279
CA $460 total
includes taxes & fees
Nov 12 - Nov 13
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 CA $352
CA $811 total
includes taxes & fees
Nov 16 - Nov 17
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A wooden deck with white railings and hanging flower baskets.

5. Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (255 reviews)
"Great clean, economical place to stay."
United States
Patrick
The price is CA $156
CA $175 total
includes taxes & fees
Nov 13 - Nov 14
Chatham Travel Lodge
Outdoor pool

6. Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (527 reviews)
"The room was clean and the staff friendly."
United States
Istvan
The price is CA $96
CA $107 total
includes taxes & fees
Nov 12 - Nov 13
Berkshire Travel Lodge
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

7. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (195 reviews)
"Great stay"
United States
George
The price is CA $138
CA $155 total
includes taxes & fees
Nov 9 - Nov 10
Micosta Leisure Inn
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

8. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (118 reviews)
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"
United States
Linda
The price is CA $230
CA $257 total
includes taxes & fees
Dec 2 - Dec 3
Inn at Silver Maple Farm
A modern dining area with wooden tables and benches, green chairs, and pendant lighting.

9. Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie
2.5 star property
West Coxsackie
8.2 out of 10, Very good, (211 reviews)
"The Hotel fits into the space - apart of the area."
United States
Richard
The price is CA $129
CA $140 total
includes taxes & fees
Nov 15 - Nov 16
Spark by Hilton West Coxsackie
A hotel room with a bed, a desk, a chair, a sofa, and a TV.

10. Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Holiday Inn Express Hotel & Suites West Coxsackie by IHG
2.5 star property
West Coxsackie
8.4 out of 10, Very good, (1,001 reviews)
"Nice staff, expensive stay."
United States
Anthony
The price is CA $139
CA $150 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
A red building with a sign reading "Shaker Mill Inn."

11. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (483 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
The price is CA $203
CA $222 total
includes taxes & fees
Nov 12 - Nov 13
Shaker Mill Inn
A large, historic building with a prominent tower and multiple domes, surrounded by autumn foliage and a lake in the background.

12. voco James Newbury Hudson Valley by IHG

voco James Newbury Hudson Valley by IHG
3.5 star property
Coxsackie
9.2 out of 10, Wonderful, (432 reviews)
"The property was quite lovely and it was nice to stay somewhere with restaurant options. The food was quite good and the views were excellent!"
United States
Lisa
The price is CA $217
CA $243 total
includes taxes & fees
Dec 6 - Dec 7
voco James Newbury Hudson Valley by IHG
A hotel room with a bed, two chairs, a small table, and a lamp.

13. Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"The best aspect of this motel is the price. It is very close to the Tanglewood concert space and in West Stockbridge, a quaint town with galleries, a good bookstore, the excellent Turnpark Outdoor Sculpture Garden and "Amici" a nice Italian restaurant, etc."
United States
James
The price is CA $98
CA $108 total
includes taxes & fees
Nov 6 - Nov 7
Pleasant Valley Motel West Stockbridge
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

14. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,000 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
United States
Lynne
The price is CA $106
CA $118 total
includes taxes & fees
Nov 25 - Nov 26
Quality Inn Great Barrington
Two Adirondack chairs facing a river with a forested hill in the background.

15. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,013 reviews)
"The location was good for our trip."
United States
Basil
The price is CA $152
CA $170 total
includes taxes & fees
Dec 6 - Dec 7
The Yankee Inn
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

16. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (939 reviews)
"Super clean and cozy and safe"
United States
Andrea
The price is CA $84
CA $93 total
includes taxes & fees
Nov 11 - Nov 12
Monument Mountain Motel
A hotel with a covered entrance, stone facade, and arched windows.

17. Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany
2.5 star property
Castleton-on-Hudson
8.8 out of 10, Excellent, (1,001 reviews)
"Great stay"
United States
barbara
The price is CA $160
CA $177 total
includes taxes & fees
Nov 29 - Nov 30
Comfort Inn & Suites East Greenbush - Albany
A wooden deck with a staircase leading to a covered porch area.

18. 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 CA $137
CA $172 total
includes taxes & fees
Nov 17 - Nov 18
All comforts of home
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

19. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.4 out of 10, Very good, (1,001 reviews)
"Room was spacious and clean"
United States
James
The price is CA $131
CA $146 total
includes taxes & fees
Dec 1 - Dec 2
Best Western Plus Berkshire Hills Inn & Suites
A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

20. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (854 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
United States
Cynthia
The price is CA $116
CA $130 total
includes taxes & fees
Dec 3 - Dec 4
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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.
View all properties

Learn more about Chatham

This charming upstate village hosts the Mac-Haydn Theatre's summer productions and a vibrant Main Street with independent shops and cafés. Explore the historic Union Station or time your visit for the Columbia County Fair, a beloved local tradition since 1841.

See all hotels in Chatham
A brick building with a green dome and columns, labeled "TRACY MEMORIAL VILLAGE HALL".

Top reviews in Chatham

An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.
Inn at Silver Maple Farm

Inn at Silver Maple Farm

Inn at Silver Maple Farm
East Chatham

10/10 Excellent

The property itself is wonderful. Chloe and Sean are delightful hosts. A great breakfast is icing on the cake.
Canada
Timothy
Reviewed June 22, 2023
Inn at Silver Maple Farm

Explore a world of travel with Expedia