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

[Hotels in Sterling](https://expedia.ca/Sterling-Hotels.d55983.Travel-Guide-Hotels)[Vacation Rentals in Sterling](https://expedia.ca/Sterling-Vacation-Rentals.d55983.Travel-Guide-VacationRentals)[Sterling Car Rentals](https://expedia.ca/Car-Rentals-In-Sterling.d55983.Car-Rental-Guide)[Sterling Vacation Packages](https://expedia.ca/Sterling.d55983.Destination-Travel-Guides)

![First Church in Sterling at 6 Meetinghouse Hill Road in historic town center of Sterling, Massachusetts MA, USA. ](https://images.trvl-media.com/place/55983/899579b2-2013-4edb-862d-73bfab65b09e.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find Winery Hotels in Sterling, MA from CA $194

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## Check availability on Sterling Winery Hotels

Tonight

[Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=55983&startDate=2025-12-11&endDate=2025-12-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=55983&startDate=2025-12-12&endDate=2025-12-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=55983&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=55983&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Sterling hotels with winery

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16700/16645/0022beaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16700/16645/c6e54f9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Junior Suite, 1 King Bed](https://images.trvl-media.com/lodging/1000000/20000/16700/16645/w3836h2561x0y0-8c0987dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pub](https://images.trvl-media.com/lodging/1000000/20000/16700/16645/23974283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Doubletree by Hilton Hotel Leominster

[](https://www.expedia.ca/Leominster-Hotels-Doubletree-By-Hilton-Hotel-Leominster.h16645.Hotel-Information)

Leominster

8.6/10

Excellent

(1001)

"Rooms clean, staff friendly. Nice bar, great breakfast buffet"

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

Leah

CA $174

CA $194 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Leominster-Hotels-Doubletree-By-Hilton-Hotel-Leominster.h16645.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111160000/111153500/111153466/df32d8a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111160000/111153500/111153466/0d8a6519.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/112000000/111160000/111153500/111153466/81662bc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111160000/111153500/111153466/e950f438.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 4-bedroom with four and half bathrooms

[](https://www.expedia.ca/Worcester-Hotels-Spacious-4-Bedroom-House-In-Wonderful-Worcester.h111153466.Hotel-Information)

Worcester

10/10

Exceptional

(5)

"We needed a place to stay while our hardwood floors were being refinished and this was perfect. We have a dog and 2 cats and there was plenty of space. The house was clean and as advertised."

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

Deb H.

CA $379

CA $692 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Worcester-Hotels-Spacious-4-Bedroom-House-In-Wonderful-Worcester.h111153466.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=2025-12-26&endDate=2025-12-27&regionId=55983&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

## Top Sterling Hotel Reviews

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