Title: Book The Best Hotels in Windsor, MA for 2025 from CA $106 - Fully Refundable Options - Expedia.ca

  

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# Find hotels in Windsor, MA from CA $106

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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=2025-10-31&d1=2025-10-31&endDate=2025-11-02&d2=2025-11-02&travelerType=family_friendly)

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=2025-10-31&d1=2025-10-31&endDate=2025-11-02&d2=2025-11-02&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=2025-10-31&d1=2025-10-31&endDate=2025-11-02&d2=2025-11-02&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=2025-10-31&d1=2025-10-31&endDate=2025-11-02&d2=2025-11-02&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=2025-10-31&d1=2025-10-31&endDate=2025-11-02&d2=2025-11-02&lodging=APARTMENT)

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=2025-10-31&d1=2025-10-31&endDate=2025-11-02&d2=2025-11-02&lodging=COTTAGE)

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=2025-10-31&d1=2025-10-31&endDate=2025-11-02&d2=2025-11-02&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=2025-10-31&d1=2025-10-31&endDate=2025-11-02&d2=2025-11-02&lodging=CONDO)

## Check prices for these dates

Tonight

[Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-10-18&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6005427&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Compare 993 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)

![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)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.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

(1008)

"Great Indian restaurant in the hotel!"

CA $149

CA $167 total

includes taxes & fees

Nov 2 - Nov 3

[](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/77000000/76300000/76297700/76297618/84274eb9.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

(764)

"We had a nice room and the food was delicious. Great place to stay. "

CA $123

CA $137 total

includes taxes & fees

Nov 2 - Nov 3

[](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)

![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)

![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f43c89bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Yankee, Trademark Collection by Wyndham

Lenox

9.0/10

Wonderful

(1011)

"Good breakfast King rooms are the best facing the mountains Recently remodeled "

CA $188

CA $210 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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

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

![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/6b95ddf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Pittsfield

8.0/10

Very good

(902)

"Excellent customer service and great rooms"

CA $145

CA $162 total

includes taxes & fees

Nov 2 - Nov 3

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

![Dining room](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/16150550.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)

![Indoor pool, outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/18127ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Village in the Berkshires

Williamstown

8.8/10

Excellent

(2076)

"Clean and great pool and hot tub facilities "

CA $129

CA $159 total

includes taxes & fees

Nov 2 - Nov 3

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

![Sundeck](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/a02c1cad.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)

![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)

### The Cornell Inn, Lenox & The Berkshires

Lenox

9.0/10

Wonderful

(1006)

"Very friendly staff. "

CA $179

CA $255 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.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/12000000/11450000/11449200/11449113/74865ec0.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)

### Berkshire Mountain Lodge

Pittsfield

9.0/10

Wonderful

(709)

"Great stay, perfect "

CA $131

CA $178 total

includes taxes & fees

Nov 2 - Nov 3

[](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)

![Indoor pool, open 6:00 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/ecbe7d49.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)

![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)

"Super friendly staff, a free coffee bar in the lobby, loads of food and shopping options within walking distance, free on-site parking - what’s not to love! And the room was spotlessly clean and very very comfortable. We love this place!!!"

CA $186

CA $208 total

includes taxes & fees

Nov 16 - Nov 17

[](https://www.expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.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/1000000/120000/119300/119210/2b026b4b.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)

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

Pittsfield

9.4/10

Exceptional

(53)

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

CA $190

CA $212 total

includes taxes & fees

Nov 2 - Nov 3

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

![Lobby lounge](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/9e766351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel On North

Pittsfield

9.6/10

Exceptional

(780)

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

CA $160

CA $179 total

includes taxes & fees

Nov 3 - Nov 4

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

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

![2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/3c0625c1.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

(757)

"Lovely spot, great accommodations, friendly staff, and great location."

CA $163

CA $202 total

includes taxes & fees

Nov 2 - Nov 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/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)

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

![Comfort Tent](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/b96863a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

 

### Huttopia Berkshires

Williamstown

10/10

Exceptional

(5)

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

CA $488

CA $545 total

includes taxes & fees

Oct 18 - Oct 19

[](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)

![Room (Firehouse)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/71ef2331.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

(1011)

"Picture perfect Inn"

CA $186

CA $271 total

includes taxes & fees

Nov 16 - Nov 17

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

![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)

![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)

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

### The Williams Inn

Williamstown

9.6/10

Exceptional

(524)

"Nice place to stay for a wedding "

CA $262

CA $292 total

includes taxes & fees

Nov 17 - Nov 18

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

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

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

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

![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/c204d876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### FairBridge Inn Express

Pittsfield

5.4/10

(796)

"Good service and people"

CA $95

CA $106 total

includes taxes & fees

Oct 19 - Oct 20

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

![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/0c3db9f2.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)

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

### Williamstown Motel

Williamstown

9.4/10

Exceptional

(304)

"Was upgraded to a larger room for no special reason. Very nice proprietor. For budget priced accommodations, this is an excellent value. Would definitely stay here again if I am in the area."

CA $109

CA $122 total

includes taxes & fees

Nov 3 - Nov 4

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

![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)

![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)

![Interior](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/f4d43d3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Constance by the Lenox Collection

Lenox

8.4/10

Very good

(553)

"Very quiet and comfortable "

CA $146

CA $164 total

includes taxes & fees

Nov 10 - Nov 11

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

![Room amenity](https://images.trvl-media.com/lodging/1000000/790000/789000/788985/6eebd994.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)

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

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

South Deerfield

7.2/10

Good

(1019)

"Great location"

CA $132

CA $147 total

includes taxes & fees

Nov 2 - Nov 3

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

![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)

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

### Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

8.6/10

Excellent

(1014)

"Good breakfast; pleasant staff on duty 24/7; convenient location."

CA $143

CA $160 total

includes taxes & fees

Nov 2 - Nov 3

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

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/fdeb3407.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/2000000/1460000/1457800/1457797/99b13181.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/d28e6aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe King Interior Suite- NO PETS ALLOWED](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/88509527.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Central Downtown Inn & Suites

Pittsfield

8.8/10

Excellent

(326)

"The rooms were large and well appointed! You could easily stay for a while and cook in the room. Nice balcony, nice living room area and very comfy bed and pillows. We enjoyed our stay very much"

CA $136

CA $152 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.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=2025-10-31&endDate=2025-11-01&regionId=6005427&adults=2&sort=RECOMMENDED&openPlayBack=true)

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## More cheap stays in Windsor

![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 $132

CA $147 total

Nov 2 - Nov 3

includes taxes & fees

7/10 Good! (1,015 reviews)

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

![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 $111

CA $124 total

Oct 19 - Oct 20

includes taxes & fees

7.4/10 Good! (808 reviews)

[](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.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 $188

CA $210 total

Nov 2 - Nov 3

includes taxes & fees

9/10 Wonderful! (1,006 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 $143

CA $160 total

Nov 2 - Nov 3

includes taxes & fees

8.4/10 Very Good! (1,014 reviews)

[](https://expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.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 $130

CA $145 total

Nov 2 - Nov 3

includes taxes & fees

8.2/10 Very Good! (1,007 reviews)

[](https://expedia.ca/Lee-Hotels-Quality-Inn.h459706.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 $95

CA $106 total

Oct 19 - Oct 20

includes taxes & fees

5.2/10 (794 reviews)

[](https://expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.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/2000000/1070000/1066500/1066423/012d1fc0_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/1000000/790000/789000/788985/20ee398b_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

![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

"Breakfast was great"

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

Posted 2 days ago

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

![Huttopia Berkshires ](//images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/137f5231_y.jpg)

### Huttopia Berkshires

5/5 Excellent

"Friendly and very accomodating staffs, They go extra mile in everything they do. Just want to mention the staffs Who helped is with our trashes even if they dont have to, They still helped us. The views in huttopia berkshire is so beautful and breath taking. Bery clean and safe surroundings with durable equipments"

A verified traveller stayed at Huttopia Berkshires

Posted 3 days ago

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

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

### Berkshires Untold

5/5 Excellent

"We had a nice room and the food was delicious. Great place to stay. "

A verified traveller stayed at Berkshires Untold

Posted 4 days ago

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

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

### Berkshire Mountain Lodge

5/5 Excellent

"Clean spacious. "

A verified traveller stayed at Berkshire Mountain Lodge

Posted 4 days ago

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

"This place is just beyond incredible! It is our 40th wedding anniversary today and so happy we found this place. "

A verified traveller from Burlington stayed at Vacation Village in the Berkshires

Posted 4 days ago

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

"Good breakfast King rooms are the best facing the mountains Recently remodeled "

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

Posted 4 days ago

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

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

### The Red Lion Inn

5/5 Excellent

A Great Weekend

"Room was comfortable and clean. The Inn is beautiful. We went to the Lions Den both evenings and had a drink and listened to live music. We couldn’t get a table at the restaurant but there are other good options in walking distance. The only disappointment was that the fireplace in our room was not working. "

A verified traveller stayed at The Red Lion Inn

Posted 5 days ago

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

![Holiday Inn & Suites Pittsfield-Berkshires by IHG](//images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg)

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

5/5 Excellent

"The bar and restaurant were excellent. Valet parking is free and fast. Ive machines should be on each floor. "

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

Posted 5 days ago

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

![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](//images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg)

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

5/5 Excellent

"Lovely spot, great accommodations, friendly staff, and great location."

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

Posted 5 days ago

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

## Frequently asked questions

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

> [Vacation Village in the Berkshires](https://www.expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information), located 13 mi (21 km) from the heart of Windsor, is a top choice for your stay based on our traveler data. Other good options for your visit to the area are [Berkshire Mountain Lodge](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) and [Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information). See all available [top hotels](https://www.expedia.ca/Hotel-Search?regionId=6005427), or [vacation rentals in Windsor](https://www.expedia.ca/Windsor-Vacation-Rentals.d6005427.Travel-Guide-VacationRentals).

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

> [Contemporary Berkshire Home with Views of Taconic Golf Course](https://www.expedia.ca/Williamstown-Hotels-Contemporary-Berkshire-Home-With-Views-Of-Taconic-Golf-Course.h112907040.Hotel-Information): This vacation home rental outside of Windsor offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. See all [vacation rentals in Windsor](https://www.expedia.ca/Windsor-Vacation-Rentals.d6005427.Travel-Guide-VacationRentals).

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

> Yes! Most hotel bookings are fully refundable provided that you cancel before the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If your reservation is non-refundable, it might still be possible to cancel it and be given a refund within 24 hours of your booking. Filter your search by [fully refundable](https://www.expedia.ca/Hotel-Search?regionId=6005427&paymentType=FREE_CANCELLATION) to find flexible hotel deals in Windsor.

### What is staying in Windsor like?

> Visitors can enjoy all that Windsor has to offer including the restaurants and shopping. In Windsor, there are 2 hotels and other accommodations to choose from. Find out more about [Windsor](https://www.expedia.ca/Windsor.dx6005427).

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

> Places to visit in the wider area include [Mount Greylock State Reservation Visitor Center](https://www.expedia.ca/Mount-Greylock-State-Reservation-Visitor-Center-Lanesborough.d6272782.Vacation-Attraction), [Mount Greylock](https://www.expedia.ca/Mount-Greylock-Adams.d6091829.Vacation-Attraction), and [Barrington Stage Company](https://www.expedia.ca/Barrington-Stage-Company-Pittsfield.d553248621532665294.Vacation-Attraction). You'll also find [Berkshire Museum](https://www.expedia.ca/Berkshire-Museum-Pittsfield.d553248621532665288.Vacation-Attraction) and [Colonial Theater](https://www.expedia.ca/Colonial-Theater-Pittsfield.d553248621532665289.Vacation-Attraction) in the area. Check out what more to see and do in Expedia's [Windsor guide](https://www.expedia.ca/Windsor.dx6005427).

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

> The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Windsor are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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

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

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