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.

Boston Lodge and Suites

Dorchester

CA $764

per person

Mar 30 - Apr 1

found 18 hours ago

Roundtrip flight included

Halifax (YHZ) to Boston (BOS)

8.4/10 Very Good! (188 reviews)

Apartment was clean and short walk from train. Staff were very friendly and helpful. Not too far from downtown Boston. Check in/check out process was very easy and convenient. If I ever find myself back in Boston, I’ll definitely see if this one is available.

Reviewed on Nov 10, 2025

Eurostars The Boxer

West End

CA $1,214

per person

May 1 - May 6

found 4 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Boston (BOS)

8.6/10 Excellent! (1,337 reviews)

I had a pleasant stay there. The receptionists are so nice and helpful. I came early before the checking time but they let me in. Extending reservation was also easy and they're helpful. They let me come back in after my buses were cancelled, and that's a very great service. They provided good amenities too. So far, it's been a comfortable stay in the hotel; and the location is quite near with the north station and stores if you need to buy meals just in case.

Reviewed on Feb 24, 2026

Raffles Boston

Back Bay

CA $3,560

per person

May 1 - May 6

found 4 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Boston (BOS)

9.6/10 Exceptional! (181 reviews)

So luxurious with a fabulous staff. I had a very nice room with a terrible view of the top of a parking garage, but I still enjoyed the room! Top-notch service. Brunch options could be a little heartier, I’m a fussy chef! Truly enjoyed my stay!

Reviewed on Feb 21, 2026

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.

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?

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.

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.

Magazine Playground

After visiting Magazine Playground, make a plan to see the other sights and activities in Springfield.

Thompson Triangle

After visiting Thompson Triangle, make a plan to see the other sights and activities in Springfield.

Best Lodging Options Near Winchester Square

MGM Springfield

One MGM Way Springfield MA

Holiday Inn Express Springfield Downtown by IHG

145 State Street Springfield MA

Hampton Inn & Suites Springfield/Downtown

851 East Columbus Ave Springfield MA

Marriott Springfield Downtown

2 Boland Way Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

100 Congress Street Springfield MA

Hilton Garden Inn-Springfield, MA

800 Hall of Fame Avenue Springfield MA

Sheraton Springfield Monarch Place Hotel

1 Monarch Place Springfield MA

Courtyard by Marriott West Springfield

885 Riverdale Street West Springfield MA

Baldwin Inn & Suites, SureStay Collection by Best Western

21 Baldwin Street West Springfield MA

See all 963 properties in Winchester Square

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.

Winchester Square Tours and Activities

Room 1

Visit Winchester Square

Plan a trip to see Winchester Square

Boston Lodge and Suites

Eurostars The Boxer

Raffles Boston

Popular places to visit

Mason Square Branch Springfield City Library

Pendleton Ave. Park

Samuel A. Bolden Park

Gunn Square Park

Magazine Playground

Thompson Triangle

Best Lodging Options Near Winchester Square

Check availability on hotels close to Winchester Square

MGM Springfield

Holiday Inn Express Springfield Downtown by IHG

Hampton Inn & Suites Springfield/Downtown

Marriott Springfield Downtown

La Quinta Inn & Suites by Wyndham Springfield MA

Hilton Garden Inn-Springfield, MA

Sheraton Springfield Monarch Place Hotel

Courtyard by Marriott West Springfield

Baldwin Inn & Suites, SureStay Collection by Best Western

The Annual Vacation Sale