Best Resorts in Chatham

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Check prices for these dates

Next weekend
Mar 6 - Mar 8
In two weeks
Mar 13 - Mar 15
In one month
Mar 27 - Mar 29
In two months
Apr 24 - Apr 26
No exact matches found, but these alternatives could be just right

Recommended hotels in Chatham

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)
"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.
$285 nightly
The price is $321
Mar 10 - Mar 11
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
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.
$286 nightly
The price is $323
Mar 3 - Mar 4
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Fridge, microwave, oven, stovetop

HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (9 reviews)
"Loved our stay! Beautiful place and the hosts were very nice. Thank you!"
United States
Kate C.
$337 nightly
The price is $380
Feb 26 - Feb 27
Total with taxes and fees
HunnyHAUS: Deluxe TINY*private spa*walk to town
Property grounds

Renovated house. Built in 1890s. No neighbors in sight.

Renovated house. Built in 1890s. No neighbors in sight.
Chatham
8.0 out of 10, Very Good, (1 review)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
$272 nightly
The price is $305
Mar 15 - Mar 16
Total with taxes and fees
Renovated house. Built in 1890s. No neighbors in sight.
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (19 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
$139 nightly
The price is $155
Mar 3 - Mar 4
Total with taxes and fees
Element Lenox Berkshires
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, (1,005 reviews)
"Very friendly and good Breakfast."
United States
Jesse
$96 nightly
The price is $107
Mar 1 - Mar 2
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites
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, (96 reviews)
"Thanksgiving stay, we’ll accommodating for the family. "
United States
Richard
$74 nightly
The price is $80
Mar 20 - Mar 21
Total with taxes and fees
Spark by Hilton West Coxsackie
View from property

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, (159 reviews)
"The cabin was very clean and cozy"
United States
Azma
$149 nightly
The price is $161
Feb 26 - Feb 27
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
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, (572 reviews)
"Excellent location!!"
United States
Abdul Samad
$75 nightly
The price is $84
Feb 26 - Feb 27
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,005 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
$87 nightly
The price is $97
Mar 25 - Mar 26
Total with taxes and fees
Quality Inn Lee - Lenox South
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, (824 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
$67 nightly
The price is $74
Feb 26 - Feb 27
Total with taxes and fees
Monument Mountain Motel
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (834 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
$69 nightly
The price is $77
Feb 26 - Feb 27
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
$95 nightly
The price is $105
Mar 3 - Mar 4
Total with taxes and fees
Shaker Mill Inn
Dining room

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (90 reviews)
"Loved the fact that we could have dinner and Sunday brunch right there."
United States
Maureen
$113 nightly
The price is $125
Feb 26 - Feb 27
Total with taxes and fees
Gregory House Country Inn
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (864 reviews)
"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "
United States
Melissa
$119 nightly
The price is $133
Feb 26 - Feb 27
Total with taxes and fees
Berkshires Untold
Exterior

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (13 reviews)
"Loved this cabin! The communal building is very clean & bathrooms are spotless. There is a farm stand near the entrance where you can buy firewood and fresh eggs. Trails are literally connected to the property for easy nature walks. We plan on coming back!"
United States
Abby L.
$165 nightly
The price is $183
Feb 26 - Feb 27
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
Deluxe Room, 1 King Bed, Ensuite (2nd Floor) | Premium bedding, individually decorated, individually furnished, desk

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (113 reviews)
"Great experience, looking forward to staying again."
United States
Greg
$150 nightly
The price is $168
Feb 26 - Feb 27
Total with taxes and fees
Changing Times Boutique Country Lodging
Desk, laptop workspace, blackout drapes, iron/ironing board

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
$59 nightly
The price is $64
Feb 26 - Feb 27
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (863 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
$142 nightly
The price is $158
Mar 27 - Mar 28
Total with taxes and fees
Berkshire Mountain Lodge
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,001 reviews)
"Clean room, great location"
United States
Andrea
$66 nightly
The price is $74
Mar 23 - Mar 24
Total with taxes and fees
Quality Inn Great Barrington
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Room was spotless! Kitchen was so helpful. Pool was a major hit with the kids and was warm even though it was February! They spent hours in the pool and outdoor hot tub. Will definitely stay here again!"
April 1-night trip
Posted 2 days ago
Berkshire Mountain Lodge

Find out more about Chatham

Chatham Resorts information

Number of reviews
7,923
Accommodation
33 Resorts
Lowest Price
$64
Highest Price
$380

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 IN AND OUT. PET FRIENDLY. - 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. Vacation Village In The Berkshires 5 Star Resort - Suite B - Family-friendly resort, 5-minute walk from Jiminy Peak Mountain Resort. 20.7 mi (33.3 km) from Chatham. Amenities include a fitness center, a car charging station, and a garden. 1 Bd - Vacation Village in the Berkshires - 20.8 mi (33.4 km) from Chatham. Access to a fitness center.
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 Van Alen House and Martin Van Buren National Historic Site.
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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