Title: Browse the Best Chatham Resorts from CA $98 | Expedia.ca

 

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# Search Resort Hotels in Chatham from CA $98

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## Check prices for these dates

Next weekend

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6046736&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Chatham Resorts

No exact matches found, but these alternatives could be just right

## Recommended hotels in Chatham

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/220997f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/837f847a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/dd672984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/6b0b575e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sugar Shack - 300 square feet of pure sweetness.

Chatham

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sue G.

CA $315

CA $524 total

includes taxes & fees

Dec 10 - Dec 11

[](https://www.expedia.ca/Chatham-Hotels-Sugar-Shack-300-Square-Feet-Of-Pure-Sweetness.h107109194.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/143defff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/f7f03fbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/f7d742eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102810000/102806400/102806391/c465f1b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Chatham

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

scott B.

CA $301

CA $504 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Chatham-Hotels-BLUSH-Boutique-TINY-Home-W-Private-Spa-Walk-To-New-Yorks-Cutest-Village.h102806391.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/84000000/83780000/83773100/83773039/3cbaf70c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83780000/83773100/83773039/2a31a137.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83780000/83773100/83773039/1894b59b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83780000/83773100/83773039/b14c2cdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### HunnyHAUS: Deluxe TINY\*private spa\*walk to town

Chatham

10/10

Exceptional

(9)

"Stag Haus provided the perfect sanctuary during a time of both celebration and grief, with thoughtful amenities and excellent local recommendations. The hot tub under the stars was exactly the therapeutic escape we needed after our last-minute booking."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Craig R.

CA $328

CA $593 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Chatham-Hotels-HunnyHAUS-Deluxe-TINYprivate-Spawalk-To-Town.h83773039.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/4ea5ab50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f43c89bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room, 1 King Bed, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f3c92221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Yankee, Trademark Collection by Wyndham

Lenox

9.2/10

Wonderful

(1014)

"Great stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ann

CA $87

CA $98 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/eac89037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/90dd9d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

8.6/10

Excellent

(1004)

"I have stayed here many times and it is consistently a comfortable, clean and quiet place."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeanine

CA $131

CA $146 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/c0933de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/754813dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Coffee/tea maker, dining tables](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/5fd0e723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Element Lenox Berkshires

Lenox

9.8/10

Exceptional

(11)

"New hotel very nice"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

joel

CA $183

CA $205 total

includes taxes & fees

Dec 11 - Dec 12

[](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/4fd790fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ba9d3ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

9.0/10

Wonderful

(1006)

"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elisabeth

CA $137

CA $153 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information)

![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/a89bc327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/2b026b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/67e1adab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Pittsfield

9.2/10

Wonderful

(64)

"Very clean room, courteous staff. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeffrey

CA $128

CA $143 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information)

![Garden](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Suite, Private Bathroom (Rockwell - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/4d5a91f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Apartment, Private Bathroom (Greylock - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/9aba043f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Suite, Private Bathroom (Garden - Pets Allowed) | Miscellaneous](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/c68ae4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shaker Mill Inn

West Stockbridge

9.6/10

Exceptional

(436)

"Nice place, easy check in"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robert

CA $143

CA $157 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information)

![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/207845f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a25612d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

8.0/10

Very good

(975)

"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Frank

CA $139

CA $155 total

includes taxes & fees

Dec 26 - Dec 27

[](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/64adfbe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/18127ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining room](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/16150550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Village in the Berkshires

Williamstown

8.8/10

Excellent

(2159)

"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Karla

CA $114

CA $143 total

includes taxes & fees

Dec 7 - Dec 8

[](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/1650f935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/1d183ca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/a9be6743.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn

Great Barrington

8.4/10

Very good

(1006)

"clean warm room. breakfast was small but good enough to start the day. coffee was delicious. quiet which was nice and also very close to the town center with shops so that was convenient "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gisselle

CA $106

CA $118 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information)

![Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/748b4faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/a1ad800b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/83dd2b57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Monument Mountain Motel

Great Barrington

9.0/10

Wonderful

(801)

"Yes it was clean & staff was very polite. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Barbara L.

[](https://www.expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/4a1ad790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/9b4c64ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshires Untold

Lenox

9.0/10

Wonderful

(806)

"We had a nice room and the food was delicious. Great place to stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Vincent

CA $153

CA $171 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information)

![Corner Studio](https://images.trvl-media.com/lodging/118000000/117880000/117877800/117877797/w4500h2996x0y0-b2a7729b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/118000000/117880000/117877800/117877797/64d93b48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/118000000/117880000/117877800/117877797/w3000h3696x0y0-3fdc44d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Studio (ADA)](https://images.trvl-media.com/lodging/118000000/117880000/117877800/117877797/6bd611cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pocketbook Hotel and Bath

Hudson

8.8/10

Excellent

(6)

"The room was very nice, and the staff was great"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kienan

CA $327

CA $433 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Hudson-Hotels-Pocketbook-Hotel-And-Bath.h117877797.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/7062b6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gazebo](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/20495b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Studio Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/5a6f7f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Howard Johnson by Wyndham Lenox

Lenox

7.6/10

Good

(827)

"Staff was very friendly and helpful."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Pamela

CA $110

CA $123 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information)

![Premium bedding, memory foam beds, individually decorated](https://images.trvl-media.com/lodging/58000000/57540000/57535200/57535178/c91ee1cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, memory foam beds, individually decorated](https://images.trvl-media.com/lodging/58000000/57540000/57535200/57535178/64920fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shared kitchen](https://images.trvl-media.com/lodging/58000000/57540000/57535200/57535178/838315b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hallway](https://images.trvl-media.com/lodging/58000000/57540000/57535200/57535178/9c0b3e3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Nautical Nest

Hudson

9.6/10

Exceptional

(123)

"We had an amazing stay! What a lovely and comfortable room, conveniently situated to shopping & so many great dining options. The shared kitchen area was well-appreciated. We would definitely return again in the future. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Robin

CA $159

CA $185 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Hudson-Hotels-Nautical-Nest.h57535178.Hotel-Information)

![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/670000/661400/661385/bcf65ef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed](https://images.trvl-media.com/lodging/1000000/670000/661400/661385/89854c51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/670000/661400/661385/b65480c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/670000/661400/661385/7bfca065.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express & Suites East Greenbush (Albany-Skyline) by IHG

Rensselaer

8.8/10

Excellent

(856)

"Friends visiting our church stayed here -- and they thought it was great! Treated very nicely by the staff; great view of Albany's skyline."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nicholas

CA $133

CA $148 total

includes taxes & fees

Dec 5 - Dec 6

[](https://www.expedia.ca/Albany-Hotels-Holiday-Inn-Express-Hotel-Suites-East-Greenbush.h661385.Hotel-Information)

![In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/a393dfb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Bedrooms, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/723a5f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/fd39ba7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Travelodge by Wyndham Great Barrington Berkshires

Great Barrington

7.6/10

Good

(561)

"The staff were very friendly and accommodating "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tom

CA $105

CA $117 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-16&endDate=2025-12-17&regionId=6046736&adults=2&lodging=HOTEL_RESORT&sort=RECOMMENDED&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

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Limited-time deals: save up to 50% on select hotels

[Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_6046736)

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## Top Chatham Hotel Reviews

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg)

### Berkshire Mountain Lodge

10/10 Excellent

"Friendly staff, room was very clean. Pool area well maintained. Overall a great place to stay"

[](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information)

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg)

### The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Great service. Attentive staff. Great location. Rooms clean and comfortable. Thanks for another great stay! "

[](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information)

![Four Points by Sheraton Albany](https://images.trvl-media.com/lodging/55000000/54080000/54077800/54077744/55bb8198_y.jpg)

### Four Points by Sheraton Albany

10/10 Excellent

"Nice people, clean room and comfortable space. "

[](https://expedia.ca/Albany-Hotels-Four-Points-By-Sheraton-Albany.h54077744.Hotel-Information)

![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg)

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"Everything was a great experience "

[](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information)

![Pocketbook Hotel and Bath](https://images.trvl-media.com/lodging/118000000/117880000/117877800/117877797/w4500h2996x0y0-b2a7729b_y.jpg)

### Pocketbook Hotel and Bath

10/10 Excellent

"Everything was anazing. There were a couple touches needed to be finishished in our room though. But they just opened "

[](https://expedia.ca/Hudson-Hotels-Pocketbook-Hotel-And-Bath.h117877797.Hotel-Information)

![Comfort Inn & Suites East Greenbush - Albany](https://images.trvl-media.com/lodging/2000000/1060000/1052400/1052319/ea181a79_y.jpg)

### Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"Good waffles"

[](https://expedia.ca/Albany-Hotels-Comfort-Inn-Suites-East-Greenbush-Albany.h1052319.Hotel-Information)

![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg)

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

10/10 Excellent

"Great"

[](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)

![Hampton Inn & Suites Albany-East Greenbush](https://images.trvl-media.com/lodging/16000000/15730000/15725300/15725242/24123a32_y.jpg)

### Hampton Inn & Suites Albany-East Greenbush

10/10 Excellent

"Comfortable beds, clean room"

[](https://expedia.ca/Albany-Hotels-Hampton-Inn-Suites-Albany-East-Greenbush.h15725242.Hotel-Information)

![Holiday Inn & Suites Pittsfield-Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg)

### Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"Everything was great. "

[](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information)

## Find out more about Chatham

## Chatham Resorts information

| Number of reviews | 11,712 |
| --- | --- |
| Accommodation | 34 Resorts |
| Lowest Price | CA $98 |
| Highest Price | CA $593 |

## 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 top-rated resort near Chatham: [Holiday Inn Club Vacations Oak 'n Spruce Resort](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h13232379.Hotel-Information) - Ski resort. 17.6 mi (28.4 km) from Chatham. Enjoy the sauna, fitness center, and 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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