Title: Book The Best Hotels in Windsor, MA for 2026 from CA $105 - Fully Refundable Options - Expedia.ca

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## Go beyond your typical stay in Windsor

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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&travelerType=family_friendly)

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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&amenities=POOL)

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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=AGRITOURISM)

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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=CABIN)

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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=APARTMENT)

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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=COTTAGE)

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=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=CONDO)

## Check prices for these dates

Tonight

[Feb 26 - Feb 27](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-02-26&endDate=2026-02-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 27 - Feb 28](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-02-27&endDate=2026-02-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-02-27&endDate=2026-03-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Windsor hotels

![Family House | Terrace/patio](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/26677985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family House | Private kitchen](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/9e3d1bdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family House | Private kitchen](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/062df4a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Double Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/182327c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Becket Motel

[](https://www.expedia.ca/Becket-Hotels-Becket-Motel.h27064222.Hotel-Information)

Becket

6.8/10

(60 reviews)

"Comfortable stay "

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

Paul

CA $137

CA $199 total

includes taxes & fees

Feb 28 - Mar 1

[](https://www.expedia.ca/Becket-Hotels-Becket-Motel.h27064222.Hotel-Information)

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

![Double Room, Accessible | Mountain view](https://images.trvl-media.com/lodging/85000000/84370000/84362200/84362148/caf79b73.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)

### Blue Vista Motor Lodge 

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

North Adams

9.8/10

Exceptional

(202 reviews)

"Great stay! "

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

ALEKSey

CA $244

CA $258 total

includes taxes & fees

Mar 2 - Mar 3

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

![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)

![Exterior](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/5f700266.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/087b92a9.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

(463 reviews)

"Nice location for my needs. Breakfast was not good or healthy. A little old, but had everything I needed. "

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

Cameron

CA $86

CA $96 total

includes taxes & fees

Feb 27 - Feb 28

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

![Lobby](https://images.trvl-media.com/lodging/28000000/27560000/27551700/27551652/d9cb5b56.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)

![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)

### Inn at Kenmore Hall

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

Richmond

10/10

Exceptional

(27 reviews)

"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 $786

CA $863 total

includes taxes & fees

Mar 4 - Mar 5

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

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

![Hallway](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/59498ff6.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)

### 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

(459 reviews)

"The great people!!!"

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

Julie

CA $197

CA $250 total

includes taxes & fees

Mar 29 - Mar 30

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

![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/4092a889.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)

![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/5a448032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/d652d2fd.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

(358 reviews)

"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 $140

CA $156 total

includes taxes & fees

Mar 2 - Mar 3

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

![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/bb79982b.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)

![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/3670f3af.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 reviews)

"Nice place for a weekend away."

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

Gregory

CA $327

CA $346 total

includes taxes & fees

Mar 4 - Mar 5

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

![Exterior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/c5994ac9.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)

![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)

### 33 Main

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

Lenox

10/10

Exceptional

(74 reviews)

"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 $630

CA $704 total

includes taxes & fees

Mar 29 - Mar 30

[](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)

![Rosalyn Elkan Suite, Cottage | Fireplace](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/01b23076.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)

![Dining](https://images.trvl-media.com/lodging/2000000/1220000/1213500/1213437/cfde231b.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 reviews)

"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."

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

Kathleen

CA $299

CA $334 total

includes taxes & fees

Mar 5 - Mar 6

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

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/b138d836.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)

![Property grounds](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/b4275c3d.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)

### Berkshire Inn

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

Pittsfield

7.8/10

Good

(844 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 $116

CA $130 total

includes taxes & fees

Mar 1 - Mar 2

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

![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)

![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/a8f10f60.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)

![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/71df138f.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

(989 reviews)

"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 $258

CA $289 total

includes taxes & fees

Mar 8 - Mar 9

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

![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)

![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)

### 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 reviews)

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

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

michael

CA $238

CA $265 total

includes taxes & fees

Mar 2 - Mar 3

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

![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/27ba18f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/bba60f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/1026298b.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)

Pittsfield

9.2/10

Wonderful

(667 reviews)

" Nice staff - beautiful hotel!"

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

MARY

CA $176

CA $197 total

includes taxes & fees

Mar 1 - Mar 2

[](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

(834 reviews)

"Clean room and the bed was very comfortable "

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

Arlan

CA $94

CA $105 total

includes taxes & fees

Mar 4 - Mar 5

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

![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)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/b11cc030.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)

![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)

### 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

(101 reviews)

"Great property, very comfortable, incredible staff, easy access to skiing in the area!"

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

Dominick

CA $163

CA $182 total

includes taxes & fees

Mar 24 - Mar 25

[](https://www.expedia.ca/East-Chatham-Hotels-Inn-At-Silver-Maple-Farm.h17094013.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/a97806ae.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)

![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

(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

Feb 28 - Mar 1

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

![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)

![Staircase](https://images.trvl-media.com/lodging/3000000/2520000/2519600/2519552/bbe2d3d2.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

(197 reviews)

"Gateways Inn is a fantastic place to stay! The staff was very courteous and the room was spacious and very clean. The breakfast was included and very tasty. I highly suggest a stay there if you are planning on visiting the Berkshires!!!"

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

Miguel

CA $244

CA $285 total

includes taxes & fees

Mar 4 - Mar 5

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

![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/1000000/790000/790000/789964/90dd9d88.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)

Pittsfield

8.6/10

Excellent

(1,005 reviews)

"Very friendly and good Breakfast."

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

Jesse

CA $131

CA $147 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.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/67000000/66250000/66244800/66244754/28728ba3.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

(290 reviews)

"Super cute place and walking distance to a bunch of great shops and food! "

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

Gina

CA $133

CA $149 total

includes taxes & fees

Mar 4 - Mar 5

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

![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)

![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)

### The Revival House

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

Adams

9.0/10

Wonderful

(26 reviews)

"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 $205

CA $229 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Adams-Hotels-The-Revival-House.h113486763.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=2026-03-12&endDate=2026-03-13&regionId=6005427&adults=2&sort=RECOMMENDED&openPlayBack=true)

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## 

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Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=HTG_SPRING_PROMO_6005427)

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## Top Windsor Hotel Reviews

## Recent Reviews in Windsor

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

### The Williams Inn

10/10 Excellent

"nice aesthetics"

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

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

### Berkshire Mountain Lodge

10/10 Excellent

"Overall pleasant stay; great facilities, staff, and location"

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

![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg)

### Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent

"clean room, friendly staff, great breakfast"

[](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.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 room, breakfast was good👍"

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

"Very spacious and comfortable. Great for families."

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

"Affordable price, clean bedroom and close to everything. "

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

![The Cornell Inn, Lenox & The Berkshires](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/e8f22f38_y.jpg)

### The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"The staff was wonderful "

[](https://expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information)

![The Porches Inn at Mass MoCA](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg)

### The Porches Inn at Mass MoCA

10/10 Excellent

"Rooms were unique. Staff friendly. Pool and hot tub open late. Would come again."

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

![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

"Yes it was clean as usual."

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

## 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 $94

CA $105 total

Mar 4 - Mar 5

includes taxes & fees

7.6/10 Good! (834 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 $118

CA $132 total

Mar 26 - Mar 27

includes taxes & fees

8.4/10 Very Good! (1,000 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 $119

CA $133 total

Mar 2 - Mar 3

includes taxes & fees

7.2/10 Good! (1,005 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 $127

CA $142 total

Mar 5 - Mar 6

includes taxes & fees

9.2/10 Wonderful! (1,017 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 $152

CA $170 total

Mar 8 - Mar 9

includes taxes & fees

9.2/10 Wonderful! (1,000 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 $186

CA $208 total

Mar 24 - Mar 25

includes taxes & fees

8.8/10 Excellent! (405 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)

## Frequently asked questions

### What is the best area to stay in Windsor?

> This central area is the heart of Windsor, offering easy pedestrian access to many of the town's key attractions. You'll find a wide selection of shops, restaurants, and pubs here, all within a short stroll of Windsor Castle and the Long Walk. The streets are generally well-kept and easy to navigate.
> 
>   
> Couples looking for a romantic getaway will find the town centre ideal. With the castle on your doorstep, charming cobbled streets, and a variety of dining options from casual to fine dining, it provides a refined and convenient base for exploring. You can easily spend your days touring the castle, enjoying a boat trip on the River Thames, or simply relaxing in one of the many cafes.
> 
>   
> Families will also appreciate the convenience of staying in the town centre. Being close to the castle means less travel time with little ones, and there are several parks nearby, including Alexandra Gardens along the river, superb for children to play.

### When is the best time to go to Windsor?

> Summer offers warm, pleasant weather, ideal for outdoor activities like hiking, fishing, and exploring the natural beauty of the Berkshire Mountains. The days are long, allowing ample time for sightseeing and enjoying the region's lakes and rivers. This is a great time for families looking for a relaxed holiday with plenty of fresh air and nature.
> 
>   
> Early autumn brings cooler temperatures and the spectacular colours of the fall foliage. This period is particularly good for couples or solo travellers who appreciate scenic drives, photography, and outdoor adventures in a picturesque setting.

### Can I cancel my hotel reservation on Expedia?

### How can I save on a Windsor hotel booking with Expedia?

### How much is the nightly rate at a Windsor hotel?

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- [Adams Vacations ](https://www.expedia.ca/Adams.d6005393.Destination-Travel-Guides)

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