Best Resorts in Chatham

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Dec 12 - Dec 14
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Resorts in Chatham

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Recommended hotels in Chatham

Terrace/patio
Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.

2.0 star property
Chatham
10.0 out of 10, Exceptional, (3)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
$332 nightly
The price is $374
Dec 10 - Dec 11
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio
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, (6)
"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.
$320 nightly
The price is $361
Dec 3 - Dec 4
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
Outdoor spa tub
HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town

Chatham
10.0 out of 10, Exceptional, (9)
"Stag Haus provided the perfect sanctuary during a time of both celebration and grief, with thoughtful amenities and excellent local recommendations. The hot tub under the stars was exactly the therapeutic escape we needed after our last-minute booking."
United States
Craig R.
$376 nightly
The price is $424
Dec 21 - Dec 22
Total with taxes and fees
HunnyHAUS: Deluxe TINY*private spa*walk to town
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1014)
"Great stay!"
United States
Ann
$62 nightly
The price is $70
Dec 14 - Dec 15
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1004)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
$93 nightly
The price is $104
Dec 4 - Dec 5
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
$131 nightly
The price is $146
Dec 11 - Dec 12
Total with taxes and fees
Element Lenox Berkshires
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1006)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
$98 nightly
The price is $109
Dec 22 - Dec 23
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (64)
"Very clean room, courteous staff. "
United States
Jeffrey
$91 nightly
The price is $102
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
$105 nightly
The price is $116
Dec 3 - Dec 4
Total with taxes and fees
Shaker Mill Inn
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (975)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$99 nightly
The price is $111
Dec 26 - Dec 27
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2157)
"Great views"
United States
Annalee
$101 nightly
The price is $113
Dec 3 - Dec 4
Total with taxes and fees
Vacation Village in the Berkshires
Lobby
Quality Inn

Quality Inn

2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1006)
"Clean room, nice location "
United States
Devron
$76 nightly
The price is $85
Dec 15 - Dec 16
Total with taxes and fees
Quality Inn
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (801)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
$67 nightly
The price is $74
Dec 3 - Dec 4
Total with taxes and fees
Monument Mountain Motel
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (806)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
$114 nightly
The price is $127
Dec 3 - Dec 4
Total with taxes and fees
Berkshires Untold
Corner Studio | In-room safe, blackout drapes, iron/ironing board, free WiFi
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2.0 star property
Hudson
8.8 out of 10, Excellent, (6)
"The room was very nice, and the staff was great"
United States
Kienan
$248 nightly
The price is $280
Dec 17 - Dec 18
Total with taxes and fees
Pocketbook Hotel and Bath
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (827)
"Staff was very friendly and helpful."
United States
Pamela
$79 nightly
The price is $88
Dec 3 - Dec 4
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Premium bedding, memory foam beds, individually decorated
Nautical Nest

Nautical Nest

2.5 star property
Hudson
9.6 out of 10, Exceptional, (123)
"We had an amazing stay! What a lovely and comfortable room, conveniently situated to shopping & so many great dining options. The shared kitchen area was well-appreciated. We would definitely return again in the future. "
United States
Robin
$114 nightly
The price is $128
Dec 8 - Dec 9
Total with taxes and fees
Nautical Nest
Free buffet breakfast
Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG

Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG

2.5 star property
Rensselaer
8.8 out of 10, Excellent, (856)
"Friends visiting our church stayed here -- and they thought it was great! Treated very nicely by the staff; great view of Albany's skyline."
United States
Nicholas
$95 nightly
The price is $106
Dec 5 - Dec 6
Total with taxes and fees
Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
Great Barrington
7.6 out of 10, Good, (560)
"The staff were very friendly and accommodating "
United States
Tom
$75 nightly
The price is $84
Dec 4 - Dec 5
Total with taxes and fees
Travelodge by Wyndham Great Barrington 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

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Great stay, great breakfast"
Peter 1-night trip
Posted 1 day ago
Hampton Inn & Suites Berkshires-Lenox

Find out more about Chatham

Chatham Resorts information

Number of reviews
11,721
Accommodation
32 Resorts
Lowest Price
$70
Highest Price
$424

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?
Our top-rated resort near Chatham: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 17.6 mi (28.4 km) from Chatham. Enjoy the sauna, fitness center, and terrace.
What can I do in Chatham?
Experience the local theater scene at The Mac-Haydn Theatre, or bring the kids to Berkshire Botanical Garden 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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