Best Resorts in Chatham

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Check prices for these dates

Next weekend
Jun 5 - Jun 7
In two weeks
Jun 12 - Jun 14
In one month
Jun 26 - Jun 28
In two months
Jul 24 - Jul 26
No exact matches found, but these alternatives could be just right

Recommended hotels in Chatham

Dining

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"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.
$296 nightly
The price is $334
Jun 1 - Jun 2
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, (7 reviews)
"The place exceeded expectations. Clean, cute space. Roomier than expected. Hot tub was on and at a good temperature. The Main Street with restaurants and bars is literally a 4 minute walk, yet the house feels secluded in a good way. Really enjoyed our stay."
United States
jack h.
$268 nightly
The price is $302
Jun 8 - Jun 9
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
Property grounds

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.6 out of 10, Exceptional, (5 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
$302 nightly
The price is $338
Jun 4 - Jun 5
Total with taxes and fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Exterior detail

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, (2 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
$468 nightly
The price is $524
Jun 4 - Jun 5
Total with taxes and fees
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
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
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,001 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
$110 nightly
The price is $123
Jun 14 - Jun 15
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
Children's activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"The property is in terrible condition."
United States
Olga V
$72 nightly
The price is $79
Jun 1 - Jun 2
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
Free daily continental breakfast

Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie
2.5 star property
West Coxsackie
7.8 out of 10, Good, (128 reviews)
"Quick stay, clean properly and convient location."
United States
Tawana
$93 nightly
The price is $100
Jun 7 - Jun 8
Total with taxes and fees
Spark by Hilton West Coxsackie
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,004 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
$92 nightly
The price is $103
Jun 7 - Jun 8
Total with taxes and fees
Quality Inn Great Barrington
Room, 2 Queen Beds, 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, (859 reviews)
"This is a great choice for folks traveling on a budget. Clean rooms, friendly owners, and nice retro vibe. Will be staying here again on my trips through the Berkshires."
United States
Mark
$86 nightly
The price is $96
Jun 2 - Jun 3
Total with taxes and fees
Monument Mountain Motel
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (467 reviews)
"The breakfast was not diabetic friendly. They stated pet friendly but no place for dog to go to the bathroom. Had to walk dog through garbage . Cigarette butts all over very the place. Beds were terrible. My towels had clumps of black hair on them. Lotion and shampoos left in room were used not new ones. Will not go back"
United States
Stacy
$73 nightly
The price is $82
Jun 1 - Jun 2
Total with taxes and fees
Berkshire Travel Lodge
Dining room

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (96 reviews)
"Comfy, cozy, quiet stay in this lovely property full of character! Thank you, hard-working staff."
United States
Leslieann H
$110 nightly
The price is $122
Jun 21 - Jun 22
Total with taxes and fees
Gregory House Country Inn
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
$120 nightly
The price is $134
Jun 1 - Jun 2
Total with taxes and fees
The Yankee Inn
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (960 reviews)
"Great location and resort. Very happy with accommodation's"
United States
Robert
$155 nightly
The price is $173
Jun 1 - Jun 2
Total with taxes and fees
Berkshire Mountain Lodge
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (457 reviews)
"Wonderful place to stay!"
United States
Mervin
$137 nightly
The price is $150
Jun 1 - Jun 2
Total with taxes and fees
Shaker Mill Inn
Exterior

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, (237 reviews)
"Really great location and near great area."
United States
Sherwin
$209 nightly
The price is $226
Jun 30 - Jul 1
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (99 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
$132 nightly
The price is $147
Jun 7 - Jun 8
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (964 reviews)
"Friendly good location"
United States
Vivian
$119 nightly
The price is $133
Jun 1 - Jun 2
Total with taxes and fees
Berkshires Untold
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,001 reviews)
"It was a clean, friendly hotel."
United States
Cheri
$113 nightly
The price is $126
Jun 3 - Jun 4
Total with taxes and fees
Quality Inn Lee - Lenox South
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, (580 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
$79 nightly
The price is $88
Jun 1 - Jun 2
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
Signature Apartment | Private kitchen | Shared fridge, espresso maker, coffee/tea maker, electric kettle

Howard Hotel

Howard Hotel
2.0 star property
Hudson
9.8 out of 10, Exceptional, (145 reviews)
"Clean room, AC ok."
United States
Rhea
$137 nightly
The price is $154
Jun 10 - Jun 11
Total with taxes and fees
Howard 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

Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

8/10 Good
"I had the King suite and it was very roomy and comfortable for an extended stay. The bed was very comfortable and housekeeping made up the room daily. The breakfast was minimal but filling. Staff interactions were pleasant and everyone was helpful with suggestions for places to eat in the local area. Nice clean facility and I would stay here again."
Jeffrey 6-night trip
Posted 3 hours ago
Country Inn & Suites by Radisson, Downtown Albany New York

Find out more about Chatham

Chatham Resorts information

Number of reviews
11,551
Accommodation
30 Resorts
Lowest Price
$79
Highest Price
$226

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 highest-rated resort near Chatham: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 17.6 mi (28.4 km) from Chatham. Amenities include a sauna, a fitness center, and a 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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