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

Best Resorts in Chatham

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Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13
No exact matches found, but these alternatives could be just right

Recommended hotels in Chatham

A wooden interior with a dining table, chairs, and a window with a view of greenery outside.

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.
$304 nightly
The price is $343
Nov 2 - Nov 3
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
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, (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.
$307 nightly
The price is $344
Oct 19 - Oct 20
Total with taxes and fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

3. 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.
$304 nightly
The price is $343
Nov 16 - Nov 17
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
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.
$556 nightly
The price is $623
Oct 19 - Oct 20
Total with taxes and fees
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, (252 reviews)
"Great clean, economical place to stay."
United States
Patrick
$112 nightly
The price is $125
Oct 18 - Oct 19
Total with taxes and fees
Chatham Travel Lodge
Outdoor pool

6. Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (518 reviews)
"Perfect as I was just needing a place to stay overnight."
United States
Kris
$75 nightly
The price is $84
Oct 21 - Oct 22
Total with taxes and fees
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
9.4 out of 10, Exceptional, (189 reviews)
"Great stay"
United States
George
$113 nightly
The price is $127
Oct 20 - Oct 21
Total with taxes and fees
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
$174 nightly
The price is $195
Nov 8 - Nov 9
Total with taxes and fees
Inn at Silver Maple Farm
A hotel room with a bed, a desk, a chair, a sofa, and a TV.

9. 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, (1,003 reviews)
"Clean."
United States
Paul J
$110 nightly
The price is $119
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
Exterior

10. 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, (422 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
$156 nightly
The price is $175
Nov 1 - Nov 2
Total with taxes and fees
voco James Newbury Hudson Valley 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, (479 reviews)
"Very nice Inn in West Stockbridge. Easy walk to center of town and short drive to all the Berkshires attractions. Room was very quiet and the grounds are wonderful. Highly recommended!"
United States
Steven
$127 nightly
The price is $139
Nov 1 - Nov 2
Total with taxes and fees
Shaker Mill Inn
A group of people performing yoga in an outdoor setting with grass and trees.

12. 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
$69 nightly
The price is $76
Oct 18 - Oct 19
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
A modern dining area with wooden tables and benches, green chairs, and pendant lighting.

13. Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie
2.5 star property
West Coxsackie
8.2 out of 10, Very good, (199 reviews)
"Clean and well maintained hotel."
United States
Uri
$114 nightly
The price is $123
Nov 15 - Nov 16
Total with taxes and fees
Spark by Hilton West Coxsackie
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

14. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"The location was good for our trip."
United States
Basil
$101 nightly
The price is $112
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
A wooden deck with a staircase leading to a covered porch area.

15. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (64 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
$118 nightly
The price is $132
Oct 20 - Oct 21
Total with taxes and fees
All comforts of home
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

16. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,003 reviews)
"good location, friendly helpful staff"
United States
Scott Patterson
$76 nightly
The price is $85
Nov 8 - Nov 9
Total with taxes and fees
Quality Inn Great Barrington
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.

17. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (621 reviews)
"The owners and staff are very helpful. The rooms are comfortable and clean."
United States
Mark
$79 nightly
The price is $88
Oct 18 - Oct 19
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
A wooden deck with a staircase leading to a covered porch area.

18. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"No frills, very clean and peaceful, beautiful setting"
United States
Lori M.
$126 nightly
The price is $141
Oct 19 - Oct 20
Total with taxes and fees
All the comforts of home
A modern hotel lobby with seating areas, tables, and a reception desk.

19. 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, (839 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
$83 nightly
The price is $93
Nov 17 - Nov 18
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

20. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (927 reviews)
"Really enjoyed our one night stay in this hotel"
United States
Aleksandr
$79 nightly
The price is $88
Oct 18 - Oct 19
Total with taxes and fees
Howard Johnson by Wyndham Lenox
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

Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

8/10 Good
"I rated many areas of this hotel as excellent but the largest negative is the location. Didn’t feel too safe as the area of Albany area is somewhat rundown and homeless individuals that seemed as though they were on substance or schizophrenic."
Treena 1-night trip
Posted 11 hours ago
Country Inn & Suites by Radisson, Downtown Albany New York

Find out more about Chatham

Chatham Resorts information

Number of reviews
7,687
Accommodation
12 Resorts
Lowest Price
$76
Highest Price
$623

Frequently asked questions

What can I expect from a resort vacation in Chatham?
You deserve a break, and a resort is the ideal place to treat yourself to the amenities and services you need for a relaxing stay in Chatham. One of the comfortable resort hotels in the surrounding area might be just what you're looking for, whether you're hoping for great restaurants on site, a state-of-the-art fitness center, or activities for the kids.
What's the best resort for my stay in Chatham?
Here are our top-rated resorts around Chatham: In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort right by Jiminy Peak Mountain Resort. 20.4 mi (32.8 km) from Chatham. Has ski-in/ski-out access, a fitness center, and a garden. COZY CABIN IN BERKSHIRES RESORT. - Ski resort right by Jiminy Peak Mountain Resort. 20.4 mi (32.8 km) from Chatham. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers. Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out - Ski resort, 5-minute walk from Jiminy Peak Mountain Resort. 20.5 mi (33 km) from Chatham. Access to ski-in/ski-out access, a fitness center, and an indoor pool.
What can I do in Chatham?
Experience the local theater scene at The Mac-Haydn Theatre, or bring the kids to Art Omi International Arts Center - Fields Sculpture Park for some family fun. In the area, other attractions include Martin Van Buren National Historic Site and Kinderhook Lake.
What's the seasonal weather like in Chatham?
The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Chatham are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around Chatham?
Fly into Hudson, NY (HCC-Columbia County), which is located 7.7 mi (12.4 km) away from the city center. Otherwise, look for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 16 mi (25.8 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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