Find Hotels with Air Conditioning in Chatham, NY

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Check availability on Chatham Hotels with Air Conditioning

Our top choices for Chatham hotels with air conditioning

Dining
Sugar Shack - 300 square feet of pure sweetness.

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 16 - Dec 17
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

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 15 - Dec 16
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
Fridge, microwave, oven, stovetop
HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (9)
"Huny House was the most artistically created space we stayed in on our entire trip! We were sooo impressed and appreciated the attention to detail!"
Canada
Patti S.
$360 nightly
The price is $406
Dec 14 - Dec 15
Total with taxes and fees
HunnyHAUS: Deluxe TINY*private spa*walk to town
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (984)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$93 nightly
The price is $104
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk
Best Western Plus Berkshire Hills Inn & Suites

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, (1000)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
$94 nightly
The price is $105
Jan 4 - Jan 5, 2026
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (437)
"Nice place, easy check in"
United States
Robert
$102 nightly
The price is $112
Dec 14 - Dec 15
Total with taxes and fees
Shaker Mill Inn
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great stay there!! Very friendly staff"
United States
Ann
$75 nightly
The price is $84
Dec 24 - Dec 25
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (804)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
$67 nightly
The price is $74
Dec 14 - Dec 15
Total with taxes and fees
Monument Mountain Motel
Mini-fridge, stovetop, cookware/dishes/utensils, paper towels
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
Catskill
9.6 out of 10, Exceptional, (107)
"The hospitality and making sure our stay was enjoyable most of all our needs during the time being. "
United States
Yessica
$159 nightly
The price is $172
Dec 14 - Dec 15
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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, (707)
"Great hospitality "
United States
regina maria
$107 nightly
The price is $120
Dec 17 - Dec 18
Total with taxes and fees
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.
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Top Chatham Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"My husband and I needed a night away between the holidaze and it was perfect! Cozy, clean and warm fireplace to nurture us during a cold snap! Shelly went above and beyond to ensure that we were comfortable and in the quietest part of the hotel. We are booking our family members there"
Sara 1-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

Why book your hotel with air conditioning in Chatham with Expedia?
Traveling should be simple, so if you're searching for hotels with air conditioning at an affordable price, Expedia can help. Keep the budget in check and go for a cheap stay with AC, or splurge and book an upscale hotel to pamper your loved ones.
How can I find cheap hotels with air conditioning in Chatham?
A good way to get cheap hotels with air conditioning in Chatham is with Expedia's easy-to-use filter tool. First, set your star rating and budget per night, then select air conditioning and your other preferred amenities to discover your dream stay at an unbeatable price.
What is there to do in Chatham near my hotel with air conditioning?
Chatham has enough sights and experiences to keep you going for weeks (or months!), starting with The Mac-Haydn Theatre. Martin Van Buren National Historic Site, Hudson Chatham Winery and Shaker Museum and Library are other popular attractions. If you're in town a while, Kinderhook Lake and Van Alen House will add the finishing touches to your itinerary.

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