Winchester Square

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.

Mason Square Branch Springfield City Library

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?

Pendleton Ave. Park

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.

Samuel A. Bolden Park

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? Visit the shops and top-notch restaurants in this family-friendly area.

Gunn Square Park

Magazine Playground

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

Magazine Playground

Thompson Triangle

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

Thompson Triangle

Top Winchester Square Hotel Deals

MGM Springfield
MGM Springfield
4 out of 5
One MGM Way, Springfield, MA
MGM Springfield
La Quinta Inn & Suites by Wyndham Springfield MA
La Quinta Inn & Suites by Wyndham Springfield MA
3 out of 5
100 Congress Street, Springfield, MA
La Quinta Inn & Suites by Wyndham Springfield MA
Sheraton Springfield Monarch Place Hotel
Sheraton Springfield Monarch Place Hotel
3.5 out of 5
1 Monarch Place, Springfield, MA
Sheraton Springfield Monarch Place Hotel
Hilton Garden Inn-Springfield, MA
Hilton Garden Inn-Springfield, MA
3 out of 5
800 Hall of Fame Avenue, Springfield, MA
Hilton Garden Inn-Springfield, MA
Best Western Springfield West Inn
Best Western Springfield West Inn
2.5 out of 5
429 Riverdale Street, West Springfield, MA
Best Western Springfield West Inn
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
106 Capital Drive, West Springfield, MA
Comfort Inn & Suites
Motel 6 Chicopee, MA - Springfield
Motel 6 Chicopee, MA - Springfield
2 out of 5
36 Burnett Rd, Chicopee, MA
Motel 6 Chicopee, MA - Springfield
See all 868 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.