Winchester Square Tours and Activities

Plan a trip to see Winchester Square

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,062, price is now CA $590 per person
CA $590
per person
Nov 1 - Nov 3
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Price was CA $1,563, price is now CA $1,038 per person
CA $1,038
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (162 reviews)
Phil’s property is immaculate and the rooms are very clean and will all required amenities. Phil’s hospitality is also top notch and it will be my place to stay in my future cape cod visits!!

Reviewed on Aug. 20, 2025

Cambria Hotel & Suites Plymouth

Cambria Hotel & Suites Plymouth

3 out of 5
Price was CA $994, price is now CA $679 per person
CA $679
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (18 reviews)
We’d love to come back here.

Reviewed on Aug. 22, 2025

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? Check out 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

Best Lodging Options Near Winchester Square

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
Holiday Inn Express Springfield Downtown by IHG

Holiday Inn Express Springfield Downtown by IHG

2.5 out of 5
145 State Street, Springfield, MA
Holiday Inn Express Springfield Downtown by IHG
Hampton Inn & Suites Springfield/Downtown

Hampton Inn & Suites Springfield/Downtown

2.5 out of 5
851 East Columbus Ave, Springfield, MA
Hampton Inn & Suites Springfield/Downtown
Marriott Springfield Downtown

Marriott Springfield Downtown

3.5 out of 5
2 Boland Way, Springfield, MA
Marriott Springfield Downtown
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
Quality Inn West Springfield

Quality Inn West Springfield

2.5 out of 5
1150 Riverdale St, West Springfield, MA
Quality Inn West Springfield
Baldwin Inn & Suites

Baldwin Inn & Suites

2 out of 5
21 Baldwin Street, West Springfield, MA
Baldwin Inn & Suites
Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

3 out of 5
885 Riverdale Street, West Springfield, MA
Courtyard by Marriott West Springfield
See all 863 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.