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=2026-03-01&d1=2026-03-01&endDate=2026-03-03&d2=2026-03-03&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=2026-03-01&d1=2026-03-01&endDate=2026-03-03&d2=2026-03-03&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=2026-03-01&d1=2026-03-01&endDate=2026-03-03&d2=2026-03-03&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=2026-03-01&d1=2026-03-01&endDate=2026-03-03&d2=2026-03-03&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=2026-03-01&d1=2026-03-01&endDate=2026-03-03&d2=2026-03-03&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=2026-03-01&d1=2026-03-01&endDate=2026-03-03&d2=2026-03-03&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=2026-03-01&d1=2026-03-01&endDate=2026-03-03&d2=2026-03-03&amenities=PETS)

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=2026-03-01&d1=2026-03-01&endDate=2026-03-03&d2=2026-03-03&lodging=CONDO)

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=2026-03-01&d1=2026-03-01&endDate=2026-03-03&d2=2026-03-03&lodging=COTTAGE)

## Check prices for these dates

Tonight

[Feb 15 - Feb 16](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-02-15&endDate=2026-02-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 16 - Feb 17](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-02-16&endDate=2026-02-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[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)

## Our top choices for Windsor hotels

![Reception](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/5f761ce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/b8545843.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room amenity](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/6eebd994.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed (Smoke Free)](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/ec8c0b54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

South Deerfield

7.2/10

Good

(1,000 reviews)

"Really nice place staff "

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

Omayra

CA $121

CA $136 total

includes taxes & fees

Feb 18 - Feb 19

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

![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4.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/a831aba7.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)

![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/47150b36.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)

Lee

8.4/10

Very good

(1,003 reviews)

"Safe, clean rooms, decent breakfast "

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

Neil

CA $115

CA $128 total

includes taxes & fees

Mar 1 - Mar 2

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

![Exterior](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/38e7a71c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/542dbb84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/7b825179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/111000000/110900000/110897100/110897047/3033684f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### UU Rowe Camp and Conference Center

[](https://www.expedia.ca/Rowe-Hotels-UU-Rowe-Camp-And-Conference-Center.h110897047.Hotel-Information)

Rowe

10/10

Exceptional

(1 review)

"Yes"

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

Stuart

CA $306

CA $324 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Rowe-Hotels-UU-Rowe-Camp-And-Conference-Center.h110897047.Hotel-Information)

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

![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/06dae0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.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)

Lenox

9.8/10

Exceptional

(18 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 $189

CA $211 total

includes taxes & fees

Feb 22 - Feb 23

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

![Gazebo](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/6df66696.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/7aabad6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/44727a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/c0f1d776.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Corner Motel

[](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information)

Williamstown

9.2/10

Wonderful

(894 reviews)

"Excellent service and a beautifully decorated property."

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

Ivana

CA $102

CA $120 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.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)

![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)

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

(1,000 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

Mar 1 - Mar 2

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

![Front of property](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/b02dfcfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/c8b24996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/fdc80b50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room dining](https://images.trvl-media.com/lodging/93000000/92330000/92321200/92321116/0bc486c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blooming Inn

[](https://www.expedia.ca/Shelburne-Falls-Hotels-Blooming-Inn.h92321116.Hotel-Information)

Shelburne Falls

9.2/10

Wonderful

(131 reviews)

"Beautiful comfortable home with many thoughtful touches"

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

Rachel

CA $127

CA $209 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Shelburne-Falls-Hotels-Blooming-Inn.h92321116.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)

![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)

### Howard Johnson by Wyndham Lenox

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

Lenox

7.6/10

Good

(831 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

Feb 16 - Feb 17

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

![Reception](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/1fb7c9f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Double Room](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/822e46eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/2c0ca8ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/45e111cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Villager Motel

[](https://www.expedia.ca/Williamstown-Hotels-The-Villager-Motel.h2832172.Hotel-Information)

Williamstown

8.8/10

Excellent

(775 reviews)

"clean modern and spacious room. comfortable king bed. "

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

William

CA $102

CA $114 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Williamstown-Hotels-The-Villager-Motel.h2832172.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)

![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)

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

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

### Shaker Mill Inn

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

West Stockbridge

9.6/10

Exceptional

(445 reviews)

"Had everything we needed. Very thoughtful touches. "

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

Mark

CA $141

CA $155 total

includes taxes & fees

Mar 1 - Mar 2

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

![Property grounds](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/1076a408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/92f285fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/25f05b7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Buffet](https://images.trvl-media.com/lodging/14000000/13280000/13279000/13278987/fb19d853.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Maple Terrace Motel

[](https://www.expedia.ca/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information)

Williamstown

9.6/10

Exceptional

(596 reviews)

"Cute place"

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

Lisa

CA $135

CA $151 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Williamstown-Hotels-Maple-Terrace-Motel.h13278987.Hotel-Information)

![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/33000000/32060000/32052900/32052899/571ba9a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Minibar, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/33000000/32060000/32052900/32052899/a9f8bbd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/33000000/32060000/32052900/32052899/46ef42a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Minibar, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/33000000/32060000/32052900/32052899/f056aa76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rodeway Inn

[](https://www.expedia.ca/Adams-Hotels-Rodeway-Inn.h32052899.Hotel-Information)

Adams

7.6/10

Good

(236 reviews)

"The room was clean and nice but i was confusing about the abandoned vehicles directly behind the hotel."

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

Anonymous traveller

CA $103

CA $115 total

includes taxes & fees

Mar 16 - Mar 17

[](https://www.expedia.ca/Adams-Hotels-Rodeway-Inn.h32052899.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/65150c76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/dccac924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/2649134b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/3ba2e773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Willows Motel Williamstown

[](https://www.expedia.ca/Williamstown-Hotels-Willows-Motel-Williamstown.h1753359.Hotel-Information)

Williamstown

9.0/10

Wonderful

(1,007 reviews)

"Very clean and warm room, kind staff, many fresh fruits for breakfast. Wonderful stay in cold January."

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

ALEXEI

CA $104

CA $116 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Williamstown-Hotels-Willows-Motel-Williamstown.h1753359.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/dcc4e9f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/w6714h4455x8y0-7f30ce4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/b2a572bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/w4000h2467x0y0-95fb3171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Pittsfield

9.2/10

Wonderful

(82 reviews)

"it was a lovely hotel, hot tub was perfect after the day of skiing, everything very clean and new and lovely breakfast. All staff were very nice."

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

Laura Pearson

CA $180

CA $201 total

includes taxes & fees

Mar 1 - Mar 2

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

![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)

![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)

![Superior Room, 1 King Bed, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/8cd694d4.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)

Lenox

9.2/10

Wonderful

(1,003 reviews)

"Very friendly staff comfy beds!"

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

Giselle

CA $126

CA $141 total

includes taxes & fees

Feb 22 - Feb 23

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

![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)

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

### Berkshires Untold

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

Lenox

9.0/10

Wonderful

(856 reviews)

"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "

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

Melissa

CA $164

CA $184 total

includes taxes & fees

Feb 18 - Feb 19

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

![Romantic Room, 1 King Bed (Room 4)](https://images.trvl-media.com/lodging/114000000/113490000/113486800/113486763/674accb2.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

(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 $204

CA $228 total

includes taxes & fees

Feb 22 - Feb 23

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

![Mountain view](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/15afb24f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/f5e7ded9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/b61eab4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/347bbac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Howard Johnson by Wyndham Williamstown

[](https://www.expedia.ca/Williamstown-Hotels-Howard-Johnson-By-Wyndham-Williamstown.h1498642.Hotel-Information)

Williamstown

6.6/10

(902 reviews)

"Great affordable place to stay while in the northern Berkshires."

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

PAUL

CA $123

CA $137 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Williamstown-Hotels-Howard-Johnson-By-Wyndham-Williamstown.h1498642.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/adb513b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/be737544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/dd484194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/19354f8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Fairfield Inn & Suites by Marriott Williamstown

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

Williamstown

8.8/10

Excellent

(405 reviews)

"Stayed one night...great breakfast"

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

Kimberley

CA $226

CA $253 total

includes taxes & fees

Feb 19 - Feb 20

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

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

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

![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/6a32b13e.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)

Lee

9.0/10

Wonderful

(1,000 reviews)

"Clean room, nice staff , decent breakfast. Overall a good stay . "

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

Anindita

CA $133

CA $149 total

includes taxes & fees

Mar 8 - Mar 9

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

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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

![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

"Fairly clean and staff were friendly"

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

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

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"Everything! :)"

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

![The Whitlock](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/f0d9797c_y.jpg)

### The Whitlock

10/10 Excellent

"Warm vibe! "

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

"Room spotless and comfortable Staff friendly and helpful Pool warm and great hot tub on below zero day"

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

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

### Berkshire Mountain Lodge

10/10 Excellent

"Perfect location, big rooms, nice staff. "

[](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

10/10 Excellent

"Bathroom had somebody’s hair on the door and shower "

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

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

### Hotel On North

10/10 Excellent

"Room was spotless, staff was amazing! Loved the bathroom setup! Will recommend and stay again! "

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

"Clean room, nice staff , decent breakfast. Overall a good stay . "

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

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

### The Williams Inn

10/10 Excellent

"A beautiful hotel to stay at while visiting the Williams campus. Our room had a nice view of the woods. Rooms were clean and with comfortable beds. The common areas of the hotel were beautiful and cozy with the fireplaces going. Easy check in and out with friendly staff."

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

Feb 16 - Feb 17

includes taxes & fees

7.4/10 Good! (830 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 $115

CA $128 total

Mar 1 - Mar 2

includes taxes & fees

8.2/10 Very Good! (1,001 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 $121

CA $136 total

Feb 18 - Feb 19

includes taxes & fees

7/10 Good! (1,008 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 $126

CA $141 total

Feb 22 - Feb 23

includes taxes & fees

9/10 Wonderful! (1,002 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 $162

CA $181 total

Mar 1 - Mar 2

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 $226

CA $253 total

Feb 19 - Feb 20

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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