Winchester Square Tours and Activities

Plan a trip to see Winchester Square

Price found within the past 48 hours. Click for updated prices.
The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was CA $1,424, price is now CA $942 per person
CA $942
per person
Mar 21 - Mar 25
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.2/10 Wonderful! (2,268 reviews)
Easy check in, courteous staff, clean rm and great view. Prudential mall across Huntington Ave..

Reviewed on Feb 2, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $3,682, price is now CA $2,340 per person
CA $2,340
per person
Apr 30 - May 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was CA $1,818, price is now CA $1,254 per person
CA $1,254
per person
Mar 21 - Mar 25
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Excellent property conveniently located in Beacon Hill. Rooms are a tad on the small side but well appointed and clean.

Reviewed on Feb 7, 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.

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
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
Marriott Springfield Downtown

Marriott Springfield Downtown

3.5 out of 5
2 Boland Way Springfield MA
Marriott Springfield Downtown
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
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
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
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
Candlewood Suites West Springfield by IHG

Candlewood Suites West Springfield by IHG

2.5 out of 5
572 Riverdale St West Springfield MA
Candlewood Suites West Springfield by IHG
Residence Inn by Marriott West Springfield

Residence Inn by Marriott West Springfield

3 out of 5
64 Border Way West Springfield MA
Residence Inn by Marriott West Springfield
See all 946 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.