Title: 2 Stars Hotels in Winchester, Boston  - Find Cheap Winchester Hotels With 2 Stars | Expedia.ca

[Winchester Travel Guide](https://expedia.ca/Winchester.dx175481)[Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d175481.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d175481.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d175481.Travel-Guide-Flights)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d175481.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d175481.Destination-Travel-Guides)

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# 2 Stars Hotels in Winchester, Boston 

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## Check availability on Winchester 2 Star Hotels

Tonight

[Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-18&endDate=2025-12-19&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-19&endDate=2025-12-20&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-19&endDate=2025-12-21&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-26&endDate=2025-12-28&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

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## Explore similar 3-star hotels

Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Winchester.

![Train to Boston! Cozy Apartment in Winchester](https://images.trvl-media.com/lodging/123000000/122310000/122304600/122304600/ca763ce6_y.jpg?impolicy=resizecrop&rw=402&ra=fit)

### Train to Boston! Cozy Apartment in Winchester

 Winchester MA

[Get rates](https://expedia.ca/Hotel-Search?startDate=01%2F01%2F2026&endDate=02%2F01%2F2026&selected=122304600&PinnedHotelID=122304600&HadPinnedHotel=true&regionId=175481)

[](https://expedia.ca/Boston-Hotels-Train-To-Boston-Cozy-Apartment-In-Winchester.h122304600.Hotel-Information)

Still don't see what you're looking for?

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You can also use these popular filters to refine your search.

[Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F12%2F2025&endDate=20%2F12%2F2025&regionId=175481&star=20&star=20&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F12%2F2025&endDate=20%2F12%2F2025&regionId=175481&star=20&star=20&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F12%2F2025&endDate=20%2F12%2F2025&regionId=175481&star=20&star=20&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F12%2F2025&endDate=20%2F12%2F2025&regionId=175481&star=20&star=20&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F12%2F2025&endDate=20%2F12%2F2025&regionId=175481&star=20&star=20&amenities=WATER_PARK)

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.

## Learn more about Winchester

Stroll along the shores of Mystic Lake, where locals gather for picnics and kayaking on sunny afternoons. History buffs can explore the Wright-Locke Farm, learning about sustainable agriculture while kids enjoy the farm animals and nature trails.

[See all hotels in Winchester](https://www.expedia.ca/Hotel-Search?startDate=2026-01-01&endDate=2026-01-02&adults=2&regionId=175481)

![Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA. ](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=900&h=600&p=1&q=high)

## Top Winchester Hotel Reviews

## Find out more about Winchester

Want to get out of town on the cheap? Thanks to the low rates and great discounts at the top 2 Stars hotels in Winchester, Winchester you can sneak away on the trip of your dreams with plenty of cash to spare. In addition to the friendly staff and well-maintained surroundings, you’ll find comfortable rooms, complimentary bath products, and quiet sleeping areas, so you can kick back with all the basic conveniences after a long day. Plus, these properties are perfect, if you need a jumping-off point for exploring the local attractions.

Several of the best hotels with 2 Stars in Winchester are situated just a stone’s throw from both public transportation and the city’s main freeways. Use the travel tools at Expedia.ca to search for options near your favorite neighborhood, find a cheap deal, and book your room. You won’t believe how inexpensive your next vacation can be when you settle in at a top two star hotel in Winchester.

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