Winchester Square

Plan a trip to see Winchester Square

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YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
26 Sept - 30 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
8.6/10 Excellent! (2,132 reviews)
I would stay here again! The rooms are as small as advertised - but the WAY that they utilize the space is truly thought-out. Every space has a purpose and we really loved that we had to be mindful of the space given. The embed was comfy, the room amenities are fantastic, the rainfall showerhead is so nice and the towel warmer is honestly the nicest touch! We'll be back for sure!

Reviewed on 9 Aug 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
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per person
24 Sept - 29 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Boston (BOS)
9.6/10 Exceptional! (135 reviews)
I had high expectations since we have been to Raffles Singapore before and after the recent renovations and it is one of our favorite hotels in the world! Glad to say that Raffles Boston did not disappoint. The hotel decor is gorgeous, thoughtfully luxurious in every detail. Location is great. Service is professional but friendly. The room butler is a convenience that cannot be overstated. Also, the first hotel that actually kept the room temperature at 66 F during the whole night. Adios, Four Seasons! Raffles is my new home in Boston.

Reviewed on 5 Aug 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
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per person
11 Sept - 16 Sept
found 19 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (428 reviews)
Had an amazing time at the Whitney. Front desk service was impeccable, friendly and was ‘just’ the added touch I would expect of a property of this caliber. I really do look forward to my next time in Boston and hope to stay at the Whitney.

Reviewed on 25 Jul 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? 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 Hotel Deals

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
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
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 out of 5
440 Memorial Dr, Chicopee, MA
Tru by Hilton Chicopee Springfield
Hampton Inn West Springfield

Hampton Inn West Springfield

2.5 out of 5
1011 Riverdale St, West Springfield, MA
Hampton Inn West Springfield
Comfort Inn & Suites West Springfield

Comfort Inn & Suites West Springfield

2.5 out of 5
106 Capital Drive, West Springfield, MA
Comfort Inn & Suites West Springfield
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 855 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.