Title: Book the Best Western Massachusetts WINERY Hotels in 2026 | Expedia.ca

[Western Massachusetts Travel Guide](https://expedia.ca/Western-Massachusetts.dx6234063)[Hotels in Western Massachusetts](https://expedia.ca/Western-Massachusetts-Hotels.d6234063.Travel-Guide-Hotels)[Vacation Rentals in Western Massachusetts](https://expedia.ca/Western-Massachusetts-Vacation-Rentals.d6234063.Travel-Guide-VacationRentals)[Flights to Western Massachusetts](https://expedia.ca/Cheap-Flights-To-Western-Massachusetts.d6234063.Travel-Guide-Flights)[Western Massachusetts Car Rentals](https://expedia.ca/Car-Rentals-In-Western-Massachusetts.d6234063.Car-Rental-Guide)[Western Massachusetts Vacation Packages](https://expedia.ca/Western-Massachusetts.d6234063.Destination-Travel-Guides)

![A panorama of western Massachusetts from the top of Mount Greylock](https://images.trvl-media.com/place/6234063/25d665be-4bef-4d30-84bb-d5865c866e81.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6234063/25d665be-4bef-4d30-84bb-d5865c866e81.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Western Massachusetts Winery Hotels

Tonight

[Feb 2 - Feb 3](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2026-02-02&endDate=2026-02-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Feb 3 - Feb 4](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2026-02-03&endDate=2026-02-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6234063&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Western Massachusetts hotels with winery

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10200/10167/5b0e9d46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/10200/10167/8bb26d95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/1000000/20000/10200/10167/99fc3d0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Business Studio Suite, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/10200/10167/3730cec4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Comfort Inn & Suites Sturbridge - Brimfield

[](https://www.expedia.ca/Sturbridge-Hotels-Comfort-Inn-Suites-Sturbridge-Brimfield.h10167.Hotel-Information)

Sturbridge

9.0/10

Wonderful

(1,002 reviews)

"Great service and a great room on a saggy night!"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

joseph

CA $128

CA $143 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Sturbridge-Hotels-Comfort-Inn-Suites-Sturbridge-Brimfield.h10167.Hotel-Information)

![Indoor pool](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/cab085ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Executive King Room](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/4ae0b464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### D. Hotel Suites & Spa

[](https://www.expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information)

Holyoke

9.2/10

Wonderful

(2,232 reviews)

"Great, great place!"

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

Richard

CA $176

CA $205 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/11000000/10270000/10260600/10260538/fb53e54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/11000000/10270000/10260600/10260538/a93f700b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![40-inch LCD TV with premium channels, TV](https://images.trvl-media.com/lodging/11000000/10270000/10260600/10260538/9b5fd8d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/11000000/10270000/10260600/10260538/7c9d16de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Inn & Suites Springfield/Downtown

[](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-Suites-Springfield-Downtown.h10260538.Hotel-Information)

South End

8.6/10

Excellent

(1,003 reviews)

"Breakfast was great and parking lot was clean of snow"

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

Jeffrey

CA $142

CA $161 total

includes taxes & fees

Feb 19 - Feb 20

[](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-Suites-Springfield-Downtown.h10260538.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/1000000/30000/20500/20447/00c971b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/53f3f179.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)

### 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

(1,001 reviews)

"Room was clean and the staff was super friendly and helpful!"

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

Ethan

CA $133

CA $149 total

includes taxes & fees

Feb 23 - Feb 24

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

![View from property](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/90293a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/8c645106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/5c3a2624.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/eaa5d51b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Courtyard by Marriott West Springfield

[](https://www.expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.Hotel-Information)

West Springfield

9.2/10

Wonderful

(596 reviews)

"Nice and very clean hotel ! "

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

Morgan

CA $172

CA $197 total

includes taxes & fees

Feb 5 - Feb 6

[](https://www.expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.Hotel-Information)

![BBQ/picnic area](https://images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/27e9804b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/1cbdfdde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Restaurant](https://images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/5f15cd40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Queen Bed with Sofa bed | Living area](https://images.trvl-media.com/lodging/2000000/1080000/1074400/1074390/b69d9716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residence Inn by Marriott Hartford Avon

[](https://www.expedia.ca/Hartford-Hotels-Residence-Inn-By-Marriott-Hartford-Avon.h1074390.Hotel-Information)

Avon

8.8/10

Excellent

(423 reviews)

"Love the hotel "

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

Carmen

CA $172

CA $198 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Hartford-Hotels-Residence-Inn-By-Marriott-Hartford-Avon.h1074390.Hotel-Information)

![Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/75dbf9d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/b642a3ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Double Room, 2 Queen Beds, Courtyard View](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/3d6dcf9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/51ca9ed5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### East Rock Inn

[](https://www.expedia.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information)

Great Barrington

9.6/10

Exceptional

(37 reviews)

"The room was clean and comfortable wi will back next year:) "

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

Nadya

CA $171

CA $192 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information)

![Premium bedding, memory foam beds, individually decorated](https://images.trvl-media.com/lodging/58000000/57540000/57535200/57535178/d9ef55ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57540000/57535200/57535178/168badea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hallway](https://images.trvl-media.com/lodging/58000000/57540000/57535200/57535178/9c0b3e3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/58000000/57540000/57535200/57535178/c3cfafba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Nautical Nest

[](https://www.expedia.ca/Hudson-Hotels-Nautical-Nest.h57535178.Hotel-Information)

Hudson

9.6/10

Exceptional

(128 reviews)

"Very cute, great location in town, nice and quiet"

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

Michael

CA $162

CA $188 total

includes taxes & fees

Feb 3 - Feb 4

[](https://www.expedia.ca/Hudson-Hotels-Nautical-Nest.h57535178.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/73ad73a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Balcony Queen](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/1845c2ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/35aa91d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/0d0e7da1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel Northampton

[](https://www.expedia.ca/Springfield-Hotels-Hotel-Northampton.h17876.Hotel-Information)

Northampton

9.2/10

Wonderful

(1,001 reviews)

"The staff were amazing and the room was perfect. "

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

Shaun

[](https://www.expedia.ca/Springfield-Hotels-Hotel-Northampton.h17876.Hotel-Information)

![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/6a441d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/f86e1269.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/882c613c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 King Bed with Sofa bed, Non Smoking (Exterior Corridor)](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/43a5af47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn & Suites Northampton - Amherst

[](https://www.expedia.ca/Springfield-Hotels-Quality-Inn-Suites-Northampton-Amherst.h24588.Hotel-Information)

Northampton

7.2/10

Good

(1,001 reviews)

"Staff was great and the room was well appointed and clean. "

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

Stephanie

CA $153

CA $171 total

includes taxes & fees

Mar 1 - Mar 2

[](https://www.expedia.ca/Springfield-Hotels-Quality-Inn-Suites-Northampton-Amherst.h24588.Hotel-Information)

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

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-16&endDate=2026-02-17&regionId=6234063&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

## Top Western Massachusetts Hotel Reviews

![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

"Immaculately clean and friendly staff. Easy parking and great breakfast"

[](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)

### Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent

"Great place, room was clean and spacious. Breakfast time could last a little longer though, ending time was 9:30am, maybe extending until 11am is best. But overall was great. "

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

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