Winchester Square

Plan a trip to see Winchester Square

Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Beautiful traditional hotel!

Reviewed on Aug 3, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (132 reviews)
Raffles is the most service oriented hotel we have ever stayed at. This place is amazing!!

Reviewed on Aug 2, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (358 reviews)
This experience from checking in to the quality of the room and the incredible concierge service that helped us with restaurants in our entire experience was unbelievable! It was probably the best experience I had with a luxury hotel in any city I visited. We will definitely be coming back!

Reviewed on Jul 20, 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
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
Howard Johnson by Wyndham Springfield

Howard Johnson by Wyndham Springfield

2 out of 5
1356 Boston Rd, Springfield, MA
Howard Johnson by Wyndham Springfield
See all 864 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.