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Check prices for these dates

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Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
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Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Chatham Resorts

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Recommended hotels in Chatham

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

Sugar Shack - 300 square feet of pure sweetness.

2.0 star property
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. "
The price is CA $392
CA $599 total
includes taxes & fees
Sep 12 - Sep 13
Sugar Shack - 300 square feet of pure sweetness.
BLUSH: Boutique TINY home*private spa*walk to town
Terrace/patio

BLUSH: Boutique TINY home*private spa*walk to town

10.0 out of 10, Exceptional, (3)
"Perfect blend of decore, comfort, and function. We went to Tanglewood which was only a half hour away. Came back to hot tub and fire pit. Beds here are soooo comfy! This is our 2nd time here and won’t be our last."
The price is CA $296
CA $471 total
includes taxes & fees
Sep 7 - Sep 8
BLUSH: Boutique TINY home*private spa*walk to town
HunnyHAUS: Deluxe TINY*private spa*walk to town
Outdoor spa tub

HunnyHAUS: Deluxe TINY*private spa*walk to town

10.0 out of 10, Exceptional, (8)
"No stone left unturned. The hot tub was clean and perfectly situated. the house was clean, with very sweet finishing touches. Within walking distance to shops. Hosts were very responsive. I highly recommend."
The price is CA $344
CA $594 total
includes taxes & fees
Aug 28 - Aug 29
HunnyHAUS: Deluxe TINY*private spa*walk to town
The Old Inn On The Green
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (88)
"Beautiful room and property. Perfect weekend getaway!"
The price is CA $399
CA $481 total
includes taxes & fees
Aug 17 - Aug 18
The Old Inn On The Green
Pilgrim Inn
Lobby

Pilgrim Inn

2.5 star property
5.8 out of 10, (313)
"Great location but no staff at check-in or checkout!"
The price is CA $109
CA $122 total
includes taxes & fees
Sep 1 - Sep 2
Pilgrim Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1000)
"Best Quality- excellent location for dining - walk to restaurants. "
The price is CA $151
CA $168 total
includes taxes & fees
Sep 1 - Sep 2
Quality Inn
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (400)
"No frills but it was a great stay!"
The price is CA $136
CA $152 total
includes taxes & fees
Sep 2 - Sep 3
Sunset Inn
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (766)
"Close to our target event a plus"
The price is CA $98
CA $109 total
includes taxes & fees
Aug 17 - Aug 18
FairBridge Inn Express
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
The price is CA $309
CA $346 total
includes taxes & fees
Sep 14 - Sep 15
Chambery Inn
Econo Lodge Lee - Great Barrington
Standard Room, 1 King Bed

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (622)
"It was lovely!"
The price is CA $88
CA $98 total
includes taxes & fees
Sep 1 - Sep 2
Econo Lodge Lee - Great Barrington
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
The price is CA $383
CA $427 total
includes taxes & fees
Sep 1 - Sep 2
Devonfield Inn B&B
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Had a wonderful time "
The price is CA $174
CA $195 total
includes taxes & fees
Sep 1 - Sep 2
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (691)
"This was our third year of two summer weeks at Oak 'n' Spruce. The accommodations are comfortable and convenient, and the staff is wonderful. We hope to be back next summer."
The price is CA $126
CA $160 total
includes taxes & fees
Sep 2 - Sep 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is CA $411
CA $727 total
includes taxes & fees
Sep 11 - Sep 12
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (14)
"Really enjoyed my stay here, definitely need a car to get around"
The price is CA $209
CA $234 total
includes taxes & fees
Aug 17 - Aug 18
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (639)
"It’s a three star hotel charging 5 star prices. They should include free breakfast."
The price is CA $208
CA $232 total
includes taxes & fees
Sep 7 - Sep 8
Hilton Garden Inn Lenox Pittsfield
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (622)
"Convenient location for my trip"
The price is CA $95
CA $106 total
includes taxes & fees
Aug 17 - Aug 18
Wagon Wheel Inn
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (783)
"My stay was perfect. I can't wait to stay there again. "
The price is CA $109
CA $121 total
includes taxes & fees
Sep 1 - Sep 2
Howard Johnson by Wyndham Lenox
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (561)
"Amazing place to stay. Can’t wait to go again. "
The price is CA $106
CA $149 total
includes taxes & fees
Sep 7 - Sep 8
Berkshire Mountain Lodge
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Great staff! Comfortable bed! "
The price is CA $198
CA $221 total
includes taxes & fees
Sep 1 - Sep 2
Hampton Inn & Suites Berkshires-Lenox
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"..."
adriana 1-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG