Best Resorts in Chatham

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Check prices for these dates

Next weekend
Feb 27 - Mar 1
In two weeks
Mar 6 - Mar 8
In one month
Mar 20 - Mar 22
In two months
Apr 17 - Apr 19
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.
$297 nightly
The price is $335
Mar 2 - Mar 3
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Property grounds

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

Renovated house. Built in 1890s. No neighbors in sight.
Chatham
$279 nightly
The price is $312
Feb 18 - Feb 19
Total with taxes and fees
Renovated house. Built in 1890s. No neighbors in sight.
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.
$297 nightly
The price is $335
Mar 9 - Mar 10
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
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.
$366 nightly
The price is $413
Feb 24 - Feb 25
Total with taxes and fees
HunnyHAUS: Deluxe TINY*private spa*walk to town
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 18 - Feb 19
Total with taxes and fees
Pleasant Valley Motel West Stockbridge
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)
"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
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, (570 reviews)
"Excellent location!!"
United States
Abdul Samad
$75 nightly
The price is $84
Feb 18 - Feb 19
Total with taxes and fees
Travelodge by Wyndham Great Barrington Berkshires
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, (154 reviews)
"The cabin was very clean and cozy"
United States
Azma
$149 nightly
The price is $161
Feb 24 - Feb 25
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,003 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
$80 nightly
The price is $89
Mar 3 - Mar 4
Total with taxes and fees
Quality Inn Lee - Lenox South
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, (833 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
$69 nightly
The price is $77
Feb 18 - Feb 19
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Lobby sitting area

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (463 reviews)
"Nice location for my needs. Breakfast was not good or healthy. A little old, but had everything I needed. "
United States
Cameron
$80 nightly
The price is $90
Feb 18 - Feb 19
Total with taxes and fees
Berkshire Travel Lodge
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 1 - Mar 2
Total with taxes and fees
Element Lenox Berkshires
Dining room

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (87 reviews)
"Loved the fact that we could have dinner and Sunday brunch right there."
United States
Maureen
$113 nightly
The price is $125
Feb 18 - Feb 19
Total with taxes and fees
Gregory House Country Inn
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, (823 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
$67 nightly
The price is $74
Feb 22 - Feb 23
Total with taxes and fees
Monument Mountain Motel
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (859 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
$124 nightly
The price is $138
Feb 18 - Feb 19
Total with taxes and fees
Berkshires Untold
Lobby

Fairfield Inn & Suites Albany East Greenbush

Fairfield Inn & Suites Albany East Greenbush
3.0 star property
East Greenbush
8.6 out of 10, Excellent, (1,003 reviews)
"Breakfast was good, hotel was quiet, liked the water and tea in the lobby."
United States
Lily
$101 nightly
The price is $112
Mar 6 - Mar 7
Total with taxes and fees
Fairfield Inn & Suites Albany East Greenbush
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, (93 reviews)
"clean place - would stay there again"
United States
Andradys
$89 nightly
The price is $97
Feb 26 - Feb 27
Total with taxes and fees
Spark by Hilton West Coxsackie
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 the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
$165 nightly
The price is $183
Feb 18 - Feb 19
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,004 reviews)
"Clean room, great location"
United States
Andrea
$76 nightly
The price is $85
Mar 2 - Mar 3
Total with taxes and fees
Quality Inn Great Barrington
Restaurant

Hampton Inn & Suites Albany-East Greenbush

Hampton Inn & Suites Albany-East Greenbush
2.5 star property
East Greenbush
9.0 out of 10, Wonderful, (899 reviews)
"Room was great, breakfast was amazing just disappointed the pool heater was broke This should be listed on the website especially when you book just for the pool. "
United States
Nevada
$106 nightly
The price is $121
Feb 20 - Feb 21
Total with taxes and fees
Hampton Inn & Suites Albany-East Greenbush
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
"Yes"
Margaret 2-night trip
Posted 2 days ago
Berkshire Mountain Lodge

Find out more about Chatham

Chatham Resorts information

Number of reviews
9,823
Accommodation
33 Resorts
Lowest Price
$64
Highest Price
$413

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. Bentley Brook the perfect home base for exploring nearby Berkshire County - 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 sauna, and 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 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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