Title: Book The Best Hotels in Windsor, MA for 2025 from CA $123 - Fully Refundable Options - Expedia.ca

  

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# Find hotels in Windsor, MA from CA $123

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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=2025-10-13&d1=2025-10-13&endDate=2025-10-15&d2=2025-10-15&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=2025-10-13&d1=2025-10-13&endDate=2025-10-15&d2=2025-10-15&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=2025-10-13&d1=2025-10-13&endDate=2025-10-15&d2=2025-10-15&lodging=CABIN)

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=2025-10-13&d1=2025-10-13&endDate=2025-10-15&d2=2025-10-15&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=2025-10-13&d1=2025-10-13&endDate=2025-10-15&d2=2025-10-15&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=2025-10-13&d1=2025-10-13&endDate=2025-10-15&d2=2025-10-15&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=2025-10-13&d1=2025-10-13&endDate=2025-10-15&d2=2025-10-15&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=2025-10-13&d1=2025-10-13&endDate=2025-10-15&d2=2025-10-15&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=2025-10-13&d1=2025-10-13&endDate=2025-10-15&d2=2025-10-15&lodging=CONDO)

## Check prices for these dates

Tonight

[Sep 29 - Sep 30](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-09-29&endDate=2025-09-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Sep 30 - Oct 1](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-09-30&endDate=2025-10-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Compare 991 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

![Non Lakeside Superior Room, 2 Queen beds](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/d3eea453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Lee

9.0/10

Wonderful

(1021)

"Great Indian restaurant in the hotel!"

CA $160

CA $179 total

includes taxes & fees

Oct 27 - Oct 28

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

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

![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![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)

### Berkshires Untold

Lenox

9.0/10

Wonderful

(737)

"Great location and very clean. Beautifully decorated and the restaurant is amazing. Just wish it offered a free breakfast with the room. "

CA $178

CA $199 total

includes taxes & fees

Sep 30 - Oct 1

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

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

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

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

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

### The Yankee, Trademark Collection by Wyndham

Lenox

9.0/10

Wonderful

(1013)

"Nice area to visit "

CA $162

CA $181 total

includes taxes & fees

Oct 1 - Oct 2

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

![Front of property](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/e8f22f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/a5a66acc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Suite, 1 Queen Bed | Living area](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/d32c867e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Suite, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/f3a87415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Cornell Inn, Lenox & The Berkshires

Lenox

9.0/10

Wonderful

(1005)

"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."

CA $178

CA $253 total

includes taxes & fees

Oct 28 - Oct 29

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

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

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

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/03675fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### Vacation Village in the Berkshires

Williamstown

8.6/10

Excellent

(2028)

"Really nice place at a reasonable price"

CA $138

CA $170 total

includes taxes & fees

Oct 20 - Oct 21

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

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/f450d89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/b51475ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/670699cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Berkshire Mountain Lodge

Pittsfield

9.0/10

Wonderful

(665)

"Very convenient set up of both room and kitchen, resort very easy to navigate. "

CA $150

CA $199 total

includes taxes & fees

Oct 19 - Oct 20

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

![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/5e762248.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/1000000/10000/3000/2943/433bbf3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/a866db4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Downstreet, an Ascend Collection Hotel

North Adams

8.8/10

Excellent

(1012)

"Property was very clean and view of mountain from window was awesome beds very comfortable and loved the hot tub and pool"

CA $202

CA $226 total

includes taxes & fees

Oct 28 - Oct 29

[](https://www.expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information)

![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Grand Room, 3 Bedrooms](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/5aedd4f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/4f7ca94f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/0fe63f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

South Lee

9.0/10

Wonderful

(740)

"The lodging was convenient to all the area attractions."

CA $181

CA $221 total

includes taxes & fees

Oct 2 - Oct 3

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

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

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

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

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

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

Pittsfield

8.0/10

Very good

(883)

"Our stay was very pleasant "

CA $137

CA $153 total

includes taxes & fees

Oct 5 - Oct 6

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

![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/651f878e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/3ef861f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/c3ea2282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel On North

Pittsfield

9.6/10

Exceptional

(776)

"Great property! Very large clean room in a unique hotel! "

CA $224

CA $251 total

includes taxes & fees

Sep 30 - Oct 1

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

![Restaurant](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/137f5231.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/3f004a6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Tent](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/e9560cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/2b2e1d76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Huttopia Berkshires

Williamstown

10/10

Exceptional

(4)

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

CA $137

CA $153 total

includes taxes & fees

Sep 30 - Oct 1

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

![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite (Main Inn Queen)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/3ac2703b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/4d2e9eec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 2 Queen Beds (Main Inn)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/5f2e6b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Red Lion Inn

Stockbridge

8.8/10

Excellent

(1009)

"great place have stayed several times, and hope to return."

CA $232

CA $322 total

includes taxes & fees

Oct 30 - Oct 31

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

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

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

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

![Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/617da859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Pittsfield

9.6/10

Exceptional

(45)

"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"

CA $176

CA $197 total

includes taxes & fees

Oct 2 - Oct 3

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

![Front of property](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/663f69c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/w2880h1917x0y0-550a94f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed with Sofa bed (Dewey Carriage House Inn)](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/468cf971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/7b669948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Constance by the Lenox Collection

Lenox

8.4/10

Very good

(546)

"Staff was so friendly and helpful. The room was small and comfortable and the grounds were well kept. "

CA $200

CA $223 total

includes taxes & fees

Oct 27 - Oct 28

[](https://www.expedia.ca/Lenox-Hotels-Rookwood-Inn.h4945461.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/3e40d6cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/7720f0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/f6ede23a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/8e0c73d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Williamstown Motel

Williamstown

9.4/10

Exceptional

(301)

"It was clean and in a convenient location "

CA $163

CA $183 total

includes taxes & fees

Oct 2 - Oct 3

[](https://www.expedia.ca/Williamstown-Hotels-Williamstown-Motel.h2758858.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hallway](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/1ea731f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/c60f19d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/d48c4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Williams Inn

Williamstown

9.6/10

Exceptional

(509)

"Great hotel, staff and restaurant!"

CA $311

CA $348 total

includes taxes & fees

Oct 29 - Oct 30

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

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

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

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

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

### Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

8.6/10

Excellent

(1012)

"Great property would certainly stay again."

CA $159

CA $177 total

includes taxes & fees

Oct 2 - Oct 3

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

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

![Exterior](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/568a1b81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/488c62c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 1 King Bed](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/6203d3bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Villager Motel

Williamstown

8.8/10

Excellent

(744)

"Perfect location for our passing through vacay."

CA $138

CA $154 total

includes taxes & fees

Oct 1 - Oct 2

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

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

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

![Aerial view](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/ddd4b2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/18aac20b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Howard Johnson by Wyndham Williamstown

Williamstown

6.6/10

(883)

"All good except needs updating in rooms and add a microwave, more updated breakfast room needed."

CA $139

CA $156 total

includes taxes & fees

Oct 1 - Oct 2

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

![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/20ee398b.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)

![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)

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

South Deerfield

7.2/10

Good

(1017)

"excellent value for the price"

CA $137

CA $153 total

includes taxes & fees

Oct 2 - Oct 3

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

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-13&endDate=2025-10-14&regionId=6005427&adults=2&sort=RECOMMENDED&openPlayBack=true)

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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, Routes 7 and 20, Lenox, MA

CA $110

CA $123 total

Sep 30 - Oct 1

includes taxes & fees

7.4/10 Good! (802 reviews)

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

![FairBridge Inn Express](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/abb5a87f_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### FairBridge Inn Express

16 Cheshire Road, Pittsfield, MA

CA $112

CA $125 total

Sep 30 - Oct 1

includes taxes & fees

5.2/10 (782 reviews)

[](https://expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.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 $137

CA $153 total

Oct 2 - Oct 3

includes taxes & fees

7/10 Good! (1,011 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 $162

CA $181 total

Oct 1 - Oct 2

includes taxes & fees

9/10 Wonderful! (1,012 reviews)

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

![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield, MA

CA $159

CA $177 total

Oct 2 - Oct 3

includes taxes & fees

8.4/10 Very Good! (1,012 reviews)

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

![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

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

1055 South Street, Pittsfield, MA

CA $176

CA $197 total

Oct 2 - Oct 3

includes taxes & fees

9.4/10 Exceptional! (43 reviews)

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

## Hotels in Windsor with star-rating

![4 Star Hotels](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_w.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/12000000/11450000/11449200/11449113/a007f019_w.jpg)

3 Star Hotels

96 properties

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

![2 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_w.jpg)

2 Star Hotels

80 properties

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

## Recent reviews of Windsor hotels

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

### Hotel On North

5/5 Excellent

"Absolutely loved every part of my stay at Hotel North. Parking was so easy and safe. The Hotel is decorated so tastefully, the staff was so welcoming. When I stepped into my room, I felt I had walked into a soothing refuge. Your decorators knew just how to balance the aesthetics with furnishings, art work, etc. Every detail was perfect - the room temperature, the comfortable bed, the quietness, etc. I will definitely recommend the Hotel North to anyone traveling to the Pittsfield area. Good job everyone!"

A verified traveller stayed at Hotel On North

Posted 3 days ago

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

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

### Best Western Plus Berkshire Hills Inn & Suites

5/5 Excellent

"Staff is friendly and accommodating "

A verified traveller stayed at Best Western Plus Berkshire Hills Inn & Suites

Posted 4 days ago

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

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

### Berkshire Mountain Lodge

5/5 Excellent

"Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again. "

A verified traveller from Weymouth stayed at Berkshire Mountain Lodge

Posted 4 days ago

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

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

### Berkshires Untold

5/5 Excellent

"What a beautiful place. I wish I could have stayed longer. Top notch!"

A verified traveller stayed at Berkshires Untold

Posted 5 days ago

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

![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](//images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg)

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

5/5 Excellent

"Very nice hotel"

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

Posted 5 days ago

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

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

### The Yankee, Trademark Collection by Wyndham

5/5 Excellent

"It's just a nice place and the staff is very nice "

A verified traveller stayed at The Yankee, Trademark Collection by Wyndham

Posted 5 days ago

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

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

### Vacation Village in the Berkshires

5/5 Excellent

"Clean, spacious, well designed room with everything needed gir a great stay …. And so much more. The balcony was a great place to sit, gave coffee etc. can’t say enough about the beautiful grounds and amenities like indoor and outdoor pool areas, etc! Enjoyed staying at Vacation Village in the Berkshire and hope to return next time I am in the area. "

A verified traveller stayed at Vacation Village in the Berkshires

Posted 6 days ago

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

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

### The Porches Inn at Mass MoCA

5/5 Excellent

"True to its historic character, the attention to detail was splendid! "

A verified traveller stayed at The Porches Inn at Mass MoCA

Posted 6 days ago

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

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

### Hampton Inn & Suites Berkshires-Lenox

5/5 Excellent

"Excellent hotel. Great staff. "

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

Posted 6 days ago

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

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-   [Inns in Peru](https://www.expedia.ca/Peru-Inns.d553248634999167831-aaInns.Travel-Guide-Accommodation)
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-   [Farmstay in Savoy](https://www.expedia.ca/Savoy-Agritourism.d6005417-aaAgritourism.Travel-Guide-Accommodation)
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-   [Flights to Savoy Mountain State Forest](https://www.expedia.ca/Cheap-Flights-To-Savoy-Mountain-State-Forest.d6339858.Travel-Guide-Flights)
-   [Flights from Adams](https://www.expedia.ca/lp/flights/6005393/flights-from-adams)
-   [Flights from Plainfield](https://www.expedia.ca/lp/flights/6005414/flights-from-plainfield)

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

-   [Dalton Vacation Rentals](https://www.expedia.ca/Dalton-Vacation-Rentals.d6911.Travel-Guide-VacationRentals)

-   [Book Hotels in Windsor on Expedia.com](https://www.expedia.com/Windsor-Hotels.d6005427.Travel-Guide-Hotels)

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