Title: Book The Best Hotels in Windsor, MA for 2026 from CA $122 - Fully Refundable Options - Expedia.ca

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# Find hotels in Windsor, MA from CA $122

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## Go beyond your typical stay in Windsor

Cabin

[](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-01-22&d1=2026-01-22&endDate=2026-01-24&d2=2026-01-24&lodging=CABIN)

Family friendly

[](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-01-22&d1=2026-01-22&endDate=2026-01-24&d2=2026-01-24&travelerType=family_friendly)

Farm

[](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-01-22&d1=2026-01-22&endDate=2026-01-24&d2=2026-01-24&lodging=AGRITOURISM)

Pool

[](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-01-22&d1=2026-01-22&endDate=2026-01-24&d2=2026-01-24&amenities=POOL)

Hot tub

[](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-01-22&d1=2026-01-22&endDate=2026-01-24&d2=2026-01-24&amenities=HOT_TUB)

Apart­ment

[](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-01-22&d1=2026-01-22&endDate=2026-01-24&d2=2026-01-24&lodging=APARTMENT)

Condo

[](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-01-22&d1=2026-01-22&endDate=2026-01-24&d2=2026-01-24&lodging=CONDO)

Pet friendly

[](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-01-22&d1=2026-01-22&endDate=2026-01-24&d2=2026-01-24&amenities=PETS)

Cottage

[](https://www.expedia.ca/Hotel-Search?destination=Windsor%2C+Massachusetts%2C+United+States+of+America&regionId=6005427&latLong=42.509022%2C-73.045715&adults=2&startDate=2026-01-22&d1=2026-01-22&endDate=2026-01-24&d2=2026-01-24&lodging=COTTAGE)

## Check prices for these dates

Tonight

[Jan 8 - Jan 9](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-01-08&endDate=2026-01-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Jan 9 - Jan 10](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-01-09&endDate=2026-01-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Windsor hotels

![Exterior](https://images.trvl-media.com/lodging/85000000/84370000/84362200/84362148/f94cd23f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/85000000/84370000/84362200/84362148/86a5bced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/85000000/84370000/84362200/84362148/954b171c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room](https://images.trvl-media.com/lodging/85000000/84370000/84362200/84362148/d0c9280e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blue Vista Motor Lodge 

[](https://www.expedia.ca/North-Adams-Hotels-Blue-Vista-Motor-Lodge.h84362148.Hotel-Information)

North Adams

9.8/10

Exceptional

(197)

"The suite I booked was very spacious and clean. I enjoyed the hot tub and sauna, fire pits and the view. A very relaxing place to stay. "

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

Jean

CA $247

CA $261 total

includes taxes & fees

Jan 12 - Jan 13

[](https://www.expedia.ca/North-Adams-Hotels-Blue-Vista-Motor-Lodge.h84362148.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/126ab2c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/bf0ac5a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/4d496801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/75ab7331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshire Travel Lodge

[](https://www.expedia.ca/Albany-Hotels-Berkshire-Travel-Lodge.h1793522.Hotel-Information)

Austerlitz

5.4/10

(461)

"The parking is right in front of the cabin the breakfast is made to order, very nice place "

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

William

CA $93

CA $104 total

includes taxes & fees

Jan 23 - Jan 24

[](https://www.expedia.ca/Albany-Hotels-Berkshire-Travel-Lodge.h1793522.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/66dde072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/a1e89c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/9b4aa931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/4417504a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Porches Inn at Mass MoCA

[](https://www.expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information)

North Adams

9.4/10

Exceptional

(452)

"It is the perfect place to stay!"

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

Darrell

CA $199

CA $253 total

includes taxes & fees

Feb 8 - Feb 9

[](https://www.expedia.ca/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/6f32fa47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, Private Bathroom (Field of Dreams)](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/903dd1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/b3ee4f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/8a6408f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Harbour House Inn

[](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information)

Cheshire

9.4/10

Exceptional

(53)

"Nice place for a weekend away."

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

Gregory

CA $279

CA $295 total

includes taxes & fees

Jan 12 - Jan 13

[](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/0ab8f96e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/ea4dc35f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/8eb2abf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Suite, 1 King Bed, Non Smoking | Living area](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/c882608e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Inn at Kenmore Hall

[](https://www.expedia.ca/Richmond-Hotels-Inn-At-Kenmore-Hall.h27551652.Hotel-Information)

Richmond

10/10

Exceptional

(27)

"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "

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

Margaret

CA $589

CA $646 total

includes taxes & fees

Jan 20 - Jan 21

[](https://www.expedia.ca/Richmond-Hotels-Inn-At-Kenmore-Hall.h27551652.Hotel-Information)

![Balcony](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/05fa2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/8d37b75c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Double Suite- NO PETS ALLOWED](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/e75ce45d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/0e28a2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Central Downtown Inn & Suites

[](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information)

Pittsfield

8.6/10

Excellent

(352)

"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."

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

Lynn

CA $130

CA $145 total

includes taxes & fees

Jan 25 - Jan 26

[](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/5bcca6ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![28-inch TV with digital channels, Netflix, pay movies](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/0db93a6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/2bb92acd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, individually decorated](https://images.trvl-media.com/lodging/13000000/12260000/12259600/12259511/d0afa322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Trail in Adams - Berkshires’ Art Hotel

[](https://www.expedia.ca/Adams-Hotels-Topia-Inn-An-Organic-Oasis.h12259511.Hotel-Information)

Adams

9.0/10

Wonderful

(144)

"Staff was great, very clean, Breakfast was terrific"

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

michael

CA $240

CA $268 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Adams-Hotels-Topia-Inn-An-Organic-Oasis.h12259511.Hotel-Information)

![Luxury Room, 1 King Bed, Bathtub](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/b3e61239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/w488h380x9y0-567859b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, individually decorated, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/225b50c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/cfdb82a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 33 Main

[](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.Hotel-Information)

Lenox

10/10

Exceptional

(74)

"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."

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

James

CA $540

CA $604 total

includes taxes & fees

Jan 15 - Jan 16

[](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/43cacb6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/cfde231b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/057b9dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/f5dca788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Terrace Inn

[](https://www.expedia.ca/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information)

Lenox

9.0/10

Wonderful

(43)

"Beautiful historic house in a great location. Responsive owner. Great visit!"

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

Abby

CA $302

CA $338 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Lenox-Hotels-Hampton-Terrace-Inn.h1213437.Hotel-Information)

![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/c3ce1b97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/de2ab5d5.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)

### Berkshire Inn

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

Pittsfield

7.8/10

Good

(841)

"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 $112

CA $126 total

includes taxes & fees

Jan 28 - Jan 29

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

![55-inch LCD TV with digital channels, printers](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/0a4a8480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Romantic Room, 1 King Bed (Room 4)](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/219287f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/f9501b50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/20208a7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Revival House

[](https://www.expedia.ca/Adams-Hotels-The-Revival-House.h113486763.Hotel-Information)

Adams

9.0/10

Wonderful

(25)

"Great place to stay one night for the Mt Greylock Road Race. Revival was convenient, close to North Adams and "

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

melissa

CA $207

CA $232 total

includes taxes & fees

Jan 13 - Jan 14

[](https://www.expedia.ca/Adams-Hotels-The-Revival-House.h113486763.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/7f42759d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/3f592f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/a8f10f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Jiminy Peak Mountain Resort

[](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information)

Hancock

8.2/10

Very good

(988)

"nice and clean, good customer service, but the room is smell. "

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

Huang

CA $303

CA $338 total

includes taxes & fees

Jan 12 - Jan 13

[](https://www.expedia.ca/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information)

![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/abb5a87f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/3ed5d9ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/1690062a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/bd64a090.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### FairBridge Inn Express

[](https://www.expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.Hotel-Information)

Pittsfield

5.4/10

(811)

"Room spotless and staff helpful."

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

William

CA $111

CA $124 total

includes taxes & fees

Jan 9 - Jan 10

[](https://www.expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/69e879d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Staircase](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/bbe2d3d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/bd7aa934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pilates](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/c06c6b54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gateways Inn & Restaurant

[](https://www.expedia.ca/Lenox-Hotels-Gateways-Inn-Restaurant.h2519552.Hotel-Information)

Lenox

8.0/10

Very good

(195)

"Very well kept property, nice restaurant and is in a great area"

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

Josephine

CA $222

CA $260 total

includes taxes & fees

Jan 11 - Jan 12

[](https://www.expedia.ca/Lenox-Hotels-Gateways-Inn-Restaurant.h2519552.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/bba60f2e.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)

![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)

### Hilton Garden Inn Lenox Pittsfield

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

Pittsfield

9.2/10

Wonderful

(660)

" Nice staff - beautiful hotel!"

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

MARY

CA $177

CA $197 total

includes taxes & fees

Jan 23 - Jan 24

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

![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/17f29286.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)

![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)

### Howard Johnson by Wyndham Lenox

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

Lenox

7.6/10

Good

(828)

"Staff was very friendly and helpful."

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

Pamela

CA $109

CA $122 total

includes taxes & fees

Jan 9 - Jan 10

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

![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/1000000/10000/2100/2067/207845f4.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)

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

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

Pittsfield

8.0/10

Very good

(1001)

"Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN"

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

Melissa

CA $130

CA $145 total

includes taxes & fees

Jan 10 - Jan 11

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

![Exterior](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/f0d9797c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/25c9c72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/047ef967.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/48ee1fed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Whitlock

[](https://www.expedia.ca/Lenox-Hotels-The-Whitlock.h66244754.Hotel-Information)

Lenox

8.6/10

Excellent

(283)

"great location"

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

Brian

CA $138

CA $154 total

includes taxes & fees

Jan 11 - Jan 12

[](https://www.expedia.ca/Lenox-Hotels-The-Whitlock.h66244754.Hotel-Information)

![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)

![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)

![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)

### Best Western Plus Berkshire Hills Inn & Suites

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

Pittsfield

8.6/10

Excellent

(1002)

"Very friendly and good Breakfast."

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

Jesse

CA $106

CA $118 total

includes taxes & fees

Jan 25 - Jan 26

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

![Aerial view](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/c9940794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pines Duplex Suite | Living area](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/445f9562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Library](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/354e34f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/f2737e42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Inn at Silver Maple Farm

[](https://www.expedia.ca/East-Chatham-Hotels-Inn-At-Silver-Maple-Farm.h17094013.Hotel-Information)

East Chatham

9.8/10

Exceptional

(98)

"Great stay, comfortable place"

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

barry

CA $178

CA $200 total

includes taxes & fees

Jan 12 - Jan 13

[](https://www.expedia.ca/East-Chatham-Hotels-Inn-At-Silver-Maple-Farm.h17094013.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.

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## More cheap stays in Windsor

![Howard Johnson by Wyndham Lenox](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

CA $109

CA $122 total

Jan 9 - Jan 10

includes taxes & fees

7.4/10 Good! (827 reviews)

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

![Quality Inn](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Quality Inn

170 Housatonic Street Lee MA

CA $113

CA $127 total

Feb 1 - Feb 2

includes taxes & fees

8.2/10 Very Good! (1,003 reviews)

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

![Red Roof Inn PLUS+ South Deerfield – Amherst](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/20ee398b_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Red Roof Inn PLUS+ South Deerfield – Amherst

9 Greenfield Rd South Deerfield MA

CA $118

CA $132 total

Jan 11 - Jan 12

includes taxes & fees

7/10 Good! (1,003 reviews)

[](https://expedia.ca/South-Deerfield-Hotels-Red-Roof-Inn-PLUS-South-Deerfield-Amherst.h788985.Hotel-Information)

![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA

CA $140

CA $156 total

Jan 15 - Jan 16

includes taxes & fees

9/10 Wonderful! (1,010 reviews)

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

![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Hampton Inn & Suites Berkshires-Lenox

445 Pittsfield Rd Lenox MA

CA $154

CA $172 total

Jan 25 - Jan 26

includes taxes & fees

9/10 Wonderful! (999 reviews)

[](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information)

![Fairfield Inn & Suites by Marriott Williamstown](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/5d49dcf2_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Fairfield Inn & Suites by Marriott Williamstown

430 Main St Williamstown MA

CA $235

CA $262 total

Jan 12 - Jan 13

includes taxes & fees

8.8/10 Excellent! (397 reviews)

[](https://expedia.ca/Williamstown-Hotels-Fairfield-Inn-Suites-By-Marriott-Williamstown.h35099355.Hotel-Information)

## Hotels in Windsor with star-rating

![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg)

4 Star Hotels

11 properties

[](https://expedia.ca/4Star-Windsor-Hotels.s40-0-d6005427.Travel-Guide-Filter-Hotels)

![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg)

3 Star Hotels

103 properties

[](https://expedia.ca/3Star-Windsor-Hotels.s30-0-d6005427.Travel-Guide-Filter-Hotels)

![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg)

2 Star Hotels

102 properties

[](https://expedia.ca/2Star-Windsor-Hotels.s20-0-d6005427.Travel-Guide-Filter-Hotels)

## Recent reviews of Windsor hotels

![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

5/5 Excellent

"Very good "

A verified traveller from Everett stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Posted 3 days ago

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

![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg)

### Hampton Inn & Suites Berkshires-Lenox

5/5 Excellent

"Very clean, modern hotel. Would definitely stay here again. "

A verified traveller stayed at Hampton Inn & Suites Berkshires-Lenox

Posted 3 days ago

[](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information)

![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg)

### The Red Lion Inn

5/5 Excellent

"Absolutely fabulous!"

A verified traveller stayed at The Red Lion Inn

Posted 3 days ago

[](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information)

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

### Berkshire Mountain Lodge

5/5 Excellent

"I've stayed here several times over the past two years. A real gem of a location, especially if you are staying several nights. "

A verified traveller stayed at Berkshire Mountain Lodge

Posted 3 days ago

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

5/5 Excellent

"Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN"

A verified traveller stayed at Holiday Inn & Suites Pittsfield-Berkshires by IHG

Posted 3 days ago

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

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

### Berkshires Untold

5/5 Excellent

"Delicious sundae! Cozy fire!"

A verified traveller stayed at Berkshires Untold

Posted 4 days ago

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

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

### Hotel On North

5/5 Excellent

"Great staff, room was huge and comfortable. "

A verified traveller stayed at Hotel On North

Posted 4 days ago

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

![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg)

### The Williams Inn

5/5 Excellent

"Very pleasant and relaxing place to stay"

A verified traveller stayed at The Williams Inn

Posted 5 days ago

[](https://expedia.ca/Williamstown-Hotels-The-Williams-Inn.h35658765.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

5/5 Excellent

"It’s a nice stop. Real level 2 EV chargers are what gets me there - amazing how hard that is to get right. It’s a bonus that it is a nice place to stay. Also appreciate real hard boiled eggs vs. whatever passes for eggs at chain hotels "

A verified traveller stayed at The Black Swan Lee - Lenox, an Ascend Collection Hotel

Posted 5 days ago

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

## Frequently asked questions

### What's the best place to stay in Windsor?

### What's the top vacation rental in Windsor?

### If I need to cancel my hotel reservation in Windsor, will I receive a refund?

### What is staying in Windsor like?

### What should I do while I'm visiting Windsor?

### What's the seasonal weather like in Windsor?

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