Title: Canaan Chalets from CA $109 | Expedia.ca

[Hotels in Canaan](https://expedia.ca/Canaan-Hotels.d55619.Travel-Guide-Hotels)[Vacation Rentals in Canaan](https://expedia.ca/Canaan-Vacation-Rentals.d55619.Travel-Guide-VacationRentals)[Flights to Canaan](https://expedia.ca/Cheap-Flights-To-Canaan.d55619.Travel-Guide-Flights)[Canaan Car Rentals](https://expedia.ca/Car-Rentals-In-Canaan.d55619.Car-Rental-Guide)[Canaan Vacation Packages](https://expedia.ca/Canaan.d55619.Destination-Travel-Guides)

![Yum](https://images.trvl-media.com/place/55619/197bfc88-eb1a-46ea-aa51-dc0f5f649d4e.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Robin/Loving Life

![](https://images.trvl-media.com/place/55619/197bfc88-eb1a-46ea-aa51-dc0f5f649d4e.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=55619&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=55619&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=55619&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=55619&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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

## Recommended hotels in Canaan

![Exterior](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/5740b713.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)

![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)

![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/83c805e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Best Western Plus Berkshire Hills Inn & Suites

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

8.6/10

Excellent

(1,002 reviews)

"Very friendly and good Breakfast."

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

Jesse

CA $131

CA $146 total

includes taxes & fees

Feb 5 - Feb 6

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

![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/e459ce18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/53f3f179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/00c971b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

9.0/10

Wonderful

(1,000 reviews)

"Room was clean and the staff was super friendly and helpful!"

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

Ethan

CA $136

CA $152 total

includes taxes & fees

Feb 6 - Feb 7

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

![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/06dae0ff.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)

![Lobby lounge](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/251da7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/3908437c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Element Lenox Berkshires

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

9.8/10

Exceptional

(16 reviews)

"Spotless rooms and the friendliest service at the front desk! "

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

Mary

CA $193

CA $216 total

includes taxes & fees

Feb 1 - Feb 2

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

![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/1000000/130000/128300/128208/1650f935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds, Non Smoking | Bathroom](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/591bd0b6.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/f25ff27c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Great Barrington

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

8.4/10

Very good

(1,000 reviews)

"My go to place for my ski weekends"

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

Ryan

CA $98

CA $109 total

includes taxes & fees

Feb 5 - Feb 6

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

![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/e2e7e72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/dcdd836c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/be126a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Holiday Inn Express Hotel & Suites Great Barrington by IHG

[](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)

8.8/10

Excellent

(722 reviews)

"Always love staying here. The staff is fantastic, amenities are great, and the breakfast is just lovely. Will be returning soon!"

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

Domenic

CA $149

CA $166 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.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)

![Premier Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/dbcc78d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3a8723ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3f4a1adf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Yankee, Trademark Collection by Wyndham

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

9.2/10

Wonderful

(1,001 reviews)

"Everything was great! "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Daphne

CA $129

CA $144 total

includes taxes & fees

Jan 25 - Jan 26

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

![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)

![Superior Suite, Private Bathroom (Honeymoon - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/7ac0f2b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bed & Breakfast in West Stockbridge

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

9.6/10

Exceptional

(441 reviews)

"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"

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

Carin

CA $147

CA $162 total

includes taxes & fees

Jan 21 - Jan 22

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

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.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/a97806ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/91284a89.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)

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

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

8.0/10

Very good

(1,000 reviews)

"Staff was very courteous and rooms clean."

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

Steven

CA $136

CA $152 total

includes taxes & fees

Jan 23 - Jan 24

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

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

![Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/44ab9667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/220f6cfe.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)

### Motel in Great Barrington

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

9.0/10

Wonderful

(817 reviews)

"Unbelieveably clean for the price."

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

Micah

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

![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/69e559b9.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)

### Motel in Lenox

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

7.6/10

Good

(829 reviews)

"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

Jan 20 - Jan 21

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/c5a54031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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, 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)

![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/e351f473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Motel in Great Barrington

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

7.6/10

Good

(566 reviews)

"Excellent location!!"

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

Abdul Samad

CA $104

CA $116 total

includes taxes & fees

Jan 20 - Jan 21

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

![Exterior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/aee2041b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb.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)

![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/6a569eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lodge in Lenox

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

9.0/10

Wonderful

(837 reviews)

"Great hospitality and beautiful design. Our family had a great time!"

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

Alison

CA $123

CA $137 total

includes taxes & fees

Jan 20 - Jan 21

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

![Exterior](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/b6081d93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/w696h390x1y0-dec65b39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/d8f6f1fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Snack bar](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/1715f4d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilton Garden Inn Lenox Pittsfield

[](https://www.expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information)

9.2/10

Wonderful

(661 reviews)

" Nice staff - beautiful hotel!"

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

MARY

CA $178

CA $199 total

includes taxes & fees

Jan 23 - Jan 24

[](https://www.expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/05418243.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/0f74ae3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/c24971a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Lee - Lenox South

[](https://www.expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information)

8.4/10

Very good

(1,000 reviews)

"Safe, clean rooms, decent breakfast "

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

Neil

CA $108

CA $120 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/ed360a9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/226579d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Villa, 3 Bedrooms](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/24f01653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

9.0/10

Wonderful

(820 reviews)

"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"

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

Stephanie

CA $157

CA $202 total

includes taxes & fees

Jan 19 - Jan 20

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

![Property entrance](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/77fe0507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/201806cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/465e60d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lodge in Pittsfield

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

9.0/10

Wonderful

(811 reviews)

"Very comfortable and very close to ski slope and restaurants"

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

Frederick

CA $137

CA $184 total

includes taxes & fees

Feb 1 - Feb 2

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

![Front of property](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/8dbc27a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/6fb451ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/ef9bad04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/f84b737e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Motel in Great Barrington

[](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information)

8.6/10

Excellent

(548 reviews)

"Perfect for pets "

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

Maria

CA $153

CA $171 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information)

![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)

![Loft Suite](https://images.trvl-media.com/lodging/118000000/117880000/117877800/117877797/f8138c6b.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)

![Bathing Studio](https://images.trvl-media.com/lodging/118000000/117880000/117877800/117877797/6463bee1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pocketbook Hotel and Bath

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

8.2/10

Very good

(16 reviews)

"The front desk was very helpful in making sure we had a good stay. "

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

Mark

CA $233

CA $327 total

includes taxes & fees

Feb 16 - Feb 17

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

![Exterior](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/cd7fa5fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow | Private kitchen](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/2d5c8478.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow | Living area](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/1e2d02da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/4ac9d6f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Camping in Williamstown

[](https://www.expedia.ca/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information)

10/10

Exceptional

(7 reviews)

"Perfect place for a relaxing getaway! We loved everything! "

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

Cammie

CA $266

CA $297 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/751d6e42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/3a99baa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/b4275c3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, Accessible](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/644deeee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Motel in Pittsfield

[](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information)

7.8/10

Good

(841 reviews)

"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."

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

MARIA J

CA $114

CA $128 total

includes taxes & fees

Jan 21 - Jan 22

[](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Inn.h297173.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=2026-01-31&endDate=2026-02-01&regionId=55619&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Private vacation homes

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Villas

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Condos

[](https://www.expedia.ca/Hotel-Search?destination=Canaan%2C+New+York%2C+United+States+of+America&regionId=55619&latLong=42.411659%2C-73.447174&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=CONDO)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Canaan%2C+New+York%2C+United+States+of+America&regionId=55619&latLong=42.411659%2C-73.447174&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=COTTAGE)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Canaan%2C+New+York%2C+United+States+of+America&regionId=55619&latLong=42.411659%2C-73.447174&adults=2&startDate=2026-04-17&d1=2026-04-17&endDate=2026-04-20&d2=2026-04-20&lodging=CABIN)

Chalets

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## Top Canaan Hotel Reviews

![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg)

### Vacation Village in the Berkshires

10/10 Excellent

"Fireplace is a nice touch "

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

![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg)

### Berkshires Untold

10/10 Excellent

"Great food, nice room, nice staff. "

[](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.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

"It’s an older property, but clean and comfortable. The staff was extremely friendly and welcoming. "

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

"Clean, very nice bed and linens, pool, jacuzzi, in room fireplace. Balcony right outside of living room. The breakfast was ok, they offered a lot but not top quality. The waffles were very good and the bacon. Overall excellent stay. Conveniently located to everything."

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

"Staff was very courteous and rooms clean."

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

![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg)

### Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"everything"

[](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)

![Hotel On North](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg)

### Hotel On North

10/10 Excellent

"Very clean hotel. Staff was so friendly and helpful. Location is perfect and own parking lot was great. "

[](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.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

"All around great hotel"

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

![Courtyard by Marriott Lenox Berkshires](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/b4c52f47_y.jpg)

### Courtyard by Marriott Lenox Berkshires

10/10 Excellent

"Our stay was great! "

[](https://expedia.ca/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information)

## Find out more about Canaan

## Canaan Chalets information

| Number of reviews | 13,893    |
| ----------------- | --------- |
| Accommodation     | 7 Chalets |
| Lowest Price      | CA $109   |
| Highest Price     | CA $327   |

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- [Holiday Park Resorts in Spencertown ](https://www.expedia.ca/Spencertown-Holiday-Parks.d3000449614-aaHolidayParks.Travel-Guide-Accommodation)
- [Spencertown Hotels ](https://www.expedia.ca/Spencertown-Hotels.d3000449614.Travel-Guide-Hotels)
- [Inns in Spencertown ](https://www.expedia.ca/Spencertown-Inns.d3000449614-aaInns.Travel-Guide-Accommodation)
- [B&B in Stephentown ](https://www.expedia.ca/Stephentown-Bed-And-Breakfast.d183723-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Cheap Hotels in Stephentown ](https://www.expedia.ca/Stephentown-Hotels-Cheap-Hotels.0-0-d183723-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Green Hotels in Stephentown ](https://www.expedia.ca/Stephentown-Hotels-Green-Sustainable.0-0-d183723-tGreenSustainable.Travel-Guide-Filter-Hotels)
- [Luxury Hotels in Stephentown ](https://www.expedia.ca/Stephentown-Hotels-Luxury-Hotel.0-0-d183723-tLuxuryHotel.Travel-Guide-Filter-Hotels)
- [Stephentown Hotels ](https://www.expedia.ca/Stephentown-Hotels.d183723.Travel-Guide-Hotels)
- [Adults Only Resorts & in Valatie ](https://www.expedia.ca/Valatie-Hotels-Adults-Only-Resorts.0-0-d183726-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels)
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- [Valatie Hotels ](https://www.expedia.ca/Valatie-Hotels.d183726.Travel-Guide-Hotels)
- [West Lebanon Hotels ](https://www.expedia.ca/West-Lebanon-Hotels.d553248635975867288.Travel-Guide-Hotels)

- [Flights to Nassau ](https://www.expedia.ca/Cheap-Flights-To-Nassau.d3000449135.Travel-Guide-Flights)
- [Flights to Niverville ](https://www.expedia.ca/Cheap-Flights-To-Niverville.d3000449167.Travel-Guide-Flights)
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- [Flights from Toronto (YYZ) to New York (NYC) ](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)

- [Visit Kinderhook ](https://www.expedia.ca/Kinderhook.dx121767)
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- [Visit Malden Bridge ](https://www.expedia.ca/Malden-Bridge.dx553248635975847470)
- [Nassau Vacations ](https://www.expedia.ca/Nassau.d3000449135.Destination-Travel-Guides)
- [Visit Niverville ](https://www.expedia.ca/Niverville.dx3000449167)
- [Shaker Museum and Library ](https://www.expedia.ca/Shaker-Museum-And-Library-Old-Chatham.d6087137.Vacation-Attraction)
- [Visit Stephentown Center ](https://www.expedia.ca/Stephentown-Center.dx553248635975871722)

- [Car rental Chatham ](https://www.expedia.ca/Car-Rentals-In-Chatham.d6046736.Car-Rental-Guide)
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- [Hertz Rental Cars in Chatham ](https://www.expedia.ca/Hertz-Car-Rentals-In-Chatham.d6046736-c40.Car-Rental-Guide-Suppliers)

- [Chatham Vacation Rentals ](https://www.expedia.ca/Chatham-Vacation-Rentals.d6046736.Travel-Guide-VacationRentals)

- [Book Chalets in Canaan on Expedia.com ](https://www.expedia.com/Canaan-Chalets.d55619-aaChalets.Travel-Guide-Accommodation)