Title: Winchester Square in Old Hill - Tours and Activities | Expedia.ca [Winchester Square Hotels](https://expedia.ca/Winchester-Square-Hotels.0-l932923619906977792-0.Travel-Guide-Filter-Hotels)[Winchester Square Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester-Square.d932923619906977792.Car-Rental-Guide)[Old Hill Vacations](https://expedia.ca/Old-Hill.d898870057799802880.Destination-Travel-Guides) # Winchester Square Tours and Activities ## Visit Winchester Square Activities * * * * * * ## Plan a trip to see Winchester Square Price found within the past 48 hours. Click for updated prices. ![Raffles Boston](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/eebc417e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Raffles Boston Back Bay CA $1,091 per person Jan 8 - Jan 11 found 1 day ago Roundtrip flight included Toronto (YYZ) to Boston (BOS) 9.6/10 Exceptional! (169 reviews) Overall, my husband & I enjoyed our stay at the Raffles -- but we weren't thrilled with the level of service we received. Specifically: - We checked in late (~11pm) due to a train delay, and the front desk informed us that our "butler" would reach out the next morning to introduce various services, etc. That never happened, which was disappointing because butler service is a Raffles staple that we were looking forward to experiencing. - Upon getting to our room, which was otherwise lovely, it became clear that the touchscreen-enabled lighting system had malfunctioned. This meant we could only have ALL the lights in the room (+ bathroom) 100% on or 100% off -- no in-between (and no dimming, etc). I alerted the front desk immediately, who offered to send an engineer "within an hour or so" -- but at that point it was nearly 12am, and we were too exhausted to wait so we declined. No one ever followed up with us or offered a solution to the issue, which grew increasingly annoying throughout our stay (e.g., I had to use my phone light to use the bathroom at night because the only other option would have been to turn ALL of the lights on 100% (and wakeup my husband). The issue also extended to the "request service" vs. "privacy please" button, so we had no way of requesting (or denying) maid service. - My husband & I celebrated our anniversary on this trip, and I let the hotel know in advance (hoping for at least a card or little treat) -- but this went 100% unacknowleged. Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-08/2026-01-11/?FromAirport=YYZ&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=911477&paandie=true&dealMarker=PhT9BsvV_5qJwxstrc3YiQxrJuC_BZN2w7OfCo-803vv8mSOIXAgxJLPxDeDh8Rs) ![The Whitney Hotel](https://images.trvl-media.com/lodging/30000000/29870000/29866100/29866090/59f2dc0e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Whitney Hotel Beacon Hill CA $1,322 per person Nov 28 - Dec 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.6/10 Exceptional! (475 reviews) Love to the room, it was perfect for what we needed. Excellent service and excellent location. We will definitely stay here again. Reviewed on Oct 13, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-28/2025-12-02/?FromAirport=YTO&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=29866090&paandie=true&dealMarker=2R2k9M0ddH0AlkOJzybby0DEOe_32KMUnVun22WEsGQfiey2BLJv-6ZUT-8R0yzM) ![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boston Harbor Hotel North End CA $1,432 per person Nov 28 - Dec 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Boston (BOS) 9.8/10 Exceptional! (1,019 reviews) Loved the hotel! Beautiful! Staff was exceptional! Reviewed on Oct 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-28/2025-12-02/?FromAirport=YTO&Destination=BOS&NumRoom=1&NumAdult=2&NumChild=0&hotelId=26146&paandie=true&dealMarker=2R2k9M0ddH0AlkOJzybby6NRB5tBJ8WtVWz5o0QQsU1mud_MnkcgwSRl2XdOlm4B) ### Popular places to visit #### Mason Square Branch Springfield City Library After visiting Mason Square Branch Springfield City Library, make a plan to see the other sights and activities in Springfield. [](https://expedia.ca/Mason-Square-Branch-Springfield-City-Library-Old-Hill.d932924068454498304.Vacation-Attraction) #### Pendleton Ave. Park Pendleton Ave. Park is just one of the places to see in Springfield, so why not enjoy the other things to explore during your travels? [](https://expedia.ca/Pendleton-Ave-Park-Old-Hill.d932923929486712832.Vacation-Attraction) #### Samuel A. Bolden Park Samuel A. Bolden Park is just one of the places to see in Springfield, so why not enjoy the other things to explore during your travels? Attend a basketball game or visit the shops in this family-friendly area. [](https://expedia.ca/Samuel-A-Bolden-Park-Springfield.d932923913554649088.Vacation-Attraction) #### Gunn Square Park Gunn Square Park is just one of the places to see in Springfield, so why not enjoy the other things to explore during your travels? Check out the shops and top-notch restaurants in this family-friendly area. [](https://expedia.ca/Gunn-Square-Park-Springfield.d932923973472387072.Vacation-Attraction) #### Magazine Playground After visiting Magazine Playground, make a plan to see the other sights and activities in Springfield. [](https://expedia.ca/Magazine-Playground-McKnight.d932923949583728640.Vacation-Attraction) #### Thompson Triangle After visiting Thompson Triangle, make a plan to see the other sights and activities in Springfield. [](https://expedia.ca/Thompson-Triangle-McKnight.d932923901724676096.Vacation-Attraction) * * * ## Best Lodging Options Near Winchester Square ## Check availability on hotels close to Winchester Square [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=2025-10-29&endDate=2025-10-30) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=2025-10-29&endDate=2025-10-30) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=2025-10-29&endDate=2025-10-30) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=2025-10-29&endDate=2025-10-30)[Oct 29 - Oct 30](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=2025-10-29&endDate=2025-10-30) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=2025-10-30&endDate=2025-10-31) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=2025-10-30&endDate=2025-10-31) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=2025-10-30&endDate=2025-10-31) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=2025-10-30&endDate=2025-10-31)[Oct 30 - Oct 31](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=2025-10-30&endDate=2025-10-31) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=31%2F10%2F2025&endDate=02%2F11%2F2025) [This weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=31%2F10%2F2025&endDate=02%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=31%2F10%2F2025&endDate=02%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=31%2F10%2F2025&endDate=02%2F11%2F2025)[Oct 31 - Nov 2](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=31%2F10%2F2025&endDate=02%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=07%2F11%2F2025&endDate=09%2F11%2F2025) [Next weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=07%2F11%2F2025&endDate=09%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=07%2F11%2F2025&endDate=09%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=07%2F11%2F2025&endDate=09%2F11%2F2025)[Nov 7 - Nov 9](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=932923619906977792&startDate=07%2F11%2F2025&endDate=09%2F11%2F2025) ![MGM Springfield](https://images.trvl-media.com/lodging/28000000/27670000/27664900/27664860/c76c1f43_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### MGM Springfield One MGM Way, Springfield, MA [](https://expedia.ca/Springfield-Hotels-MGM-Springfield.h27664860.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Springfield MA](https://images.trvl-media.com/lodging/1000000/20000/18100/18056/71c77a60_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Springfield MA 100 Congress Street, Springfield, MA [](https://expedia.ca/Springfield-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Springfield-MA.h18056.Hotel-Information) ![Hilton Garden Inn-Springfield, MA](https://images.trvl-media.com/lodging/1000000/900000/892100/892040/2726a1b6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Garden Inn-Springfield, MA 800 Hall of Fame Avenue, Springfield, MA [](https://expedia.ca/Springfield-Hotels-Hilton-Garden-Inn-Springfield.h892040.Hotel-Information) ![Hampton Inn & Suites Springfield/Downtown](https://images.trvl-media.com/lodging/11000000/10270000/10260600/10260538/8fe97c17_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn & Suites Springfield/Downtown 851 East Columbus Ave, Springfield, MA [](https://expedia.ca/Springfield-Hotels-Hampton-Inn-Suites-Springfield-Downtown.h10260538.Hotel-Information) ![Marriott Springfield Downtown](https://images.trvl-media.com/lodging/1000000/10000/6300/6279/c4768c07_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Marriott Springfield Downtown 2 Boland Way, Springfield, MA [](https://expedia.ca/Springfield-Hotels-Tower-Square-Hotel-Springfield.h6279.Hotel-Information) ![Sheraton Springfield Monarch Place Hotel](https://images.trvl-media.com/lodging/1000000/30000/21500/21419/74f0d068_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sheraton Springfield Monarch Place Hotel 1 Monarch Place, Springfield, MA [](https://expedia.ca/Springfield-Hotels-Sheraton-Springfield-Monarch-Place-Hotel.h21419.Hotel-Information) ![Quality Inn West Springfield](https://images.trvl-media.com/lodging/1000000/10000/7500/7486/7f7ace74_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Quality Inn West Springfield 1150 Riverdale St, West Springfield, MA [](https://expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information) ![Baldwin Inn & Suites, SureStay Collection by Best Western](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/43807f20_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Baldwin Inn & Suites, SureStay Collection by Best Western 21 Baldwin Street, West Springfield, MA [](https://expedia.ca/Springfield-Hotels-Regency-Inn-Suites.h15705.Hotel-Information) ![Courtyard by Marriott West Springfield](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/90293a2b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Courtyard by Marriott West Springfield 885 Riverdale Street, West Springfield, MA [](https://expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.Hotel-Information) [See all 898 properties in Winchester Square](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=932923619906977792) 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.