Winchester Square

Plan a trip to see Winchester Square

Price found within the past 48 hours. Click for updated prices.
The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was ￥413,542, price is now ￥309,323 per person
￥309,323
per person
Dec 27 - Jan 3
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.4/10 Exceptional! (1,005 reviews)
Clean, easy check in, quiet, in walking distance of everything we need-our favorite place to stay always!

Reviewed on Oct 11, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was ￥7,023,027, price is now ￥3,495,172 per person
￥3,495,172
per person
Dec 27 - Jan 3
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.8/10 Exceptional! (160 reviews)
I wish the water was hotter, had to ask to have room cleaned after 1st day as housekeeping did not come. Very responsive though when inquiries made.

Reviewed on Oct 7, 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was ￥462,948, price is now ￥343,538 per person
￥343,538
per person
Dec 27 - Jan 3
just found
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.4/10 Exceptional! (510 reviews)
Great location but they have no concierge , and for the price you will think they would. Rooms are small

Reviewed on Oct 8, 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

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
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way, Springfield, MA
MGM Springfield
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
Marriott Springfield Downtown

Marriott Springfield Downtown

3.5 out of 5
2 Boland Way, Springfield, MA
Marriott Springfield Downtown
Motel 6 Chicopee, MA - Springfield

Motel 6 Chicopee, MA - Springfield

2 out of 5
36 Burnett Rd, Chicopee, MA
Motel 6 Chicopee, MA - Springfield
Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western

2.5 out of 5
21 Baldwin Street, West Springfield, MA
Baldwin Inn & Suites, SureStay Collection by Best Western
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 886 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.