Search Hotels Near Winchester Square, Springfield

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Our top choices for Winchester Square hotels

Exterior
Holiday Inn Express Springfield Downtown by IHG

Holiday Inn Express Springfield Downtown by IHG

Holiday Inn Express Springfield Downtown by IHG
2.5 star property
Metro Center, 2 km from Winchester Square
9.0 out of 10, Wonderful, (1078)
"Great stay"
United States
Desiree
The price is ฿3,586
฿4,069 total
includes taxes & fees
23 Dec - 24 Dec
Holiday Inn Express Springfield Downtown by IHG
8 restaurants, breakfast, lunch, dinner served; American cuisine
MGM Springfield

MGM Springfield

MGM Springfield
4.0 star property
Metro Center, 2.4 km from Winchester Square
9.0 out of 10, Wonderful, (1457)
"Great room, nice venue, with free self parking "
United States
Chuck
The price is ฿4,688
฿6,032 total
includes taxes & fees
4 Jan - 5 Jan 2026
MGM Springfield
Lobby
Hampton Inn & Suites Springfield/Downtown

Hampton Inn & Suites Springfield/Downtown

Hampton Inn & Suites Springfield/Downtown
2.5 star property
South End, 2.4 km from Winchester Square
8.6 out of 10, Excellent, (1000)
"Clean rooms, close to everything, breakfast included"
United States
Haily
The price is ฿3,227
฿3,661 total
includes taxes & fees
30 Dec - 31 Dec
Hampton Inn & Suites Springfield/Downtown
Indoor pool
Hilton Garden Inn-Springfield, MA

Hilton Garden Inn-Springfield, MA

Hilton Garden Inn-Springfield, MA
3.0 star property
South End, 2.6 km from Winchester Square
8.6 out of 10, Excellent, (1004)
"Very nice hotel, clean and friendly perfectly located. "
United States
Brandy
The price is ฿3,717
฿4,217 total
includes taxes & fees
23 Dec - 24 Dec
Hilton Garden Inn-Springfield, MA
Reception
Marriott Springfield Downtown

Marriott Springfield Downtown

Marriott Springfield Downtown
3.5 star property
Metro Center, 2.5 km from Winchester Square
8.0 out of 10, Very good, (989)
"It was nice and updated. Staff was amazing. "
United States
Awildo
The price is ฿4,104
฿4,656 total
includes taxes & fees
22 Dec - 23 Dec
Marriott Springfield Downtown
Indoor pool, pool loungers
Sheraton Springfield Monarch Place Hotel

Sheraton Springfield Monarch Place Hotel

Sheraton Springfield Monarch Place Hotel
3.5 star property
Metro Center, 2.5 km from Winchester Square
8.0 out of 10, Very good, (1001)
"Breakfast was the best, friendly staff!!"
United States
Carla
The price is ฿4,530
฿5,155 total
includes taxes & fees
15 Jan - 16 Jan 2026
Sheraton Springfield Monarch Place Hotel
Exterior
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA
3.0 star property
Metro Center, 2.5 km from Winchester Square
8.0 out of 10, Very good, (1307)
"Great staff, very clean property, and good breakfast. "
United States
Jasmine
The price is ฿3,476
฿3,944 total
includes taxes & fees
21 Dec - 22 Dec
La Quinta Inn & Suites by Wyndham Springfield MA
Room (Louis XIV) | Individually decorated, individually furnished, iron/ironing board
Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights, 3.6 km from Winchester Square
9.0 out of 10, Wonderful, (423)
"Artful and inspiring interior decorating and delicious French toast for breakfast!"
United States
Marielle
The price is ฿3,305
฿3,750 total
includes taxes & fees
18 Dec - 19 Dec
Naomi's Inn Bed & Breakfast
Comfort House, 4 Bedrooms, Non Smoking | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Upscaled Home in a Quiet Neighborhood

Upscaled Home in a Quiet Neighborhood

Upscaled Home in a Quiet Neighborhood
3.0 star property
Forest Park, 3.8 km from Winchester Square
8.4 out of 10, Very good, (5)
"So clean and comfy"
United States
Anonymous traveller
The price is ฿9,910
฿15,333 total
includes taxes & fees
18 Dec - 19 Dec
Upscaled Home in a Quiet Neighborhood
Lobby
Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield

Red Roof Inn PLUS+ West Springfield
2.5 star property
6 km from Winchester Square
6.8 out of 10, (1003)
"Great like always "
United States
Sharee
The price is ฿2,662
฿3,046 total
includes taxes & fees
24 Dec - 25 Dec
Red Roof Inn PLUS+ West Springfield
Lobby sitting area
Motel 6 Chicopee, MA - Springfield

Motel 6 Chicopee, MA - Springfield

Motel 6 Chicopee, MA - Springfield
2.0 star property
6.1 km from Winchester Square
6.6 out of 10, (1002)
"Clean awesome rooms nice staff check in easy and fast"
United States
Tucker
The price is ฿2,378
฿2,761 total
includes taxes & fees
24 Dec - 25 Dec
Motel 6 Chicopee, MA - Springfield
Individually furnished, desk, blackout curtains, iron/ironing board
Howard Johnson by Wyndham Springfield

Howard Johnson by Wyndham Springfield

Howard Johnson by Wyndham Springfield
2.0 star property
Boston Road, 6.4 km from Winchester Square
6.6 out of 10, (1001)
"Room was clean the people were nice easy check in it was very quiet "
United States
Christopher
The price is ฿2,865
฿3,250 total
includes taxes & fees
18 Dec - 19 Dec
Howard Johnson by Wyndham Springfield
View from property
Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield

Courtyard by Marriott West Springfield
3.0 star property
5.4 km from Winchester Square
9.2 out of 10, Wonderful, (584)
"Quiet, convenient… a bit pricey "
United States
Mihai
The price is ฿3,717
฿4,254 total
includes taxes & fees
11 Jan - 12 Jan 2026
Courtyard by Marriott West Springfield
Lobby
Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel

Blue – A Modern Hotel, an Ascend Collection Hotel
2.5 star property
5.7 km from Winchester Square
9.6 out of 10, Exceptional, (107)
"Great staff super nice beautiful hotel lots of parking "
United States
Yovelys
The price is ฿3,717
฿4,254 total
includes taxes & fees
12 Jan - 13 Jan 2026
Blue – A Modern Hotel, an Ascend Collection Hotel
Standard Double Room, 2 Double Beds, Non Smoking | Premium bedding, desk, iron/ironing board, rollaway beds
Quality Inn Chicopee - Springfield

Quality Inn Chicopee - Springfield

Quality Inn Chicopee - Springfield
2.5 star property
6.7 km from Winchester Square
6.4 out of 10, (838)
"Breakfast was convenient, loved coffee in the lobby and staff very friendly. "
United States
Julia
The price is ฿2,928
฿3,321 total
includes taxes & fees
4 Jan - 5 Jan 2026
Quality Inn Chicopee - Springfield
Exterior
Candlewood Suites West Springfield by IHG

Candlewood Suites West Springfield by IHG

Candlewood Suites West Springfield by IHG
2.5 star property
5.2 km from Winchester Square
8.4 out of 10, Very good, (802)
"Love the staff"
United States
Sherry
The price is ฿3,085
฿3,531 total
includes taxes & fees
6 Jan - 7 Jan 2026
Candlewood Suites West Springfield by IHG
Room amenity
Riverdale Inn

Riverdale Inn

Riverdale Inn
2.0 star property
6.5 km from Winchester Square
5.8 out of 10, (1000)
"Staff was nice"
United States
Amanda
The price is ฿2,308
฿2,641 total
includes taxes & fees
24 Dec - 25 Dec
Riverdale Inn
Exterior
Best Western Springfield West Inn

Best Western Springfield West Inn

Best Western Springfield West Inn
2.5 star property
5 km from Winchester Square
7.8 out of 10, Good, (1001)
"Decent breakfast"
United States
Jennifer
The price is ฿2,941
฿3,366 total
includes taxes & fees
24 Dec - 25 Dec
Best Western Springfield West Inn
Standard Room, 2 Queen Beds, Non Smoking | Pillow-top beds, desk, laptop workspace, blackout curtains
Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western
2.5 star property
4.7 km from Winchester Square
7.6 out of 10, Good, (104)
"At the moment breakfast isn’t being served but not a big deal, parking was very easy and close to the entrance not much walking having to be done, staff was very friendly and accommodating the place was very clean and very quiet definitely worth the money in my opinion looking forward to staying again "
United States
Victor
The price is ฿3,189
฿3,650 total
includes taxes & fees
31 Dec - 1 Jan 2026
Baldwin Inn & Suites, SureStay Collection by Best Western
Lobby
Hampton Inn West Springfield

Hampton Inn West Springfield

Hampton Inn West Springfield
2.5 star property
5.5 km from Winchester Square
8.2 out of 10, Very good, (1002)
"nearby eateries"
United States
Majorie
The price is ฿3,070
฿3,513 total
includes taxes & fees
25 Dec - 26 Dec
Hampton Inn West Springfield
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.
View all properties

Top Winchester Square Hotel Reviews

Baldwin Inn & Suites, SureStay Collection by Best Western

Baldwin Inn & Suites, SureStay Collection by Best Western

10/10 Excellent
"At the moment breakfast isn’t being served but not a big deal, parking was very easy and close to the entrance not much walking having to be done, staff was very friendly and accommodating the place was very clean and very quiet definitely worth the money in my opinion looking forward to staying again "
Victor 2-night trip
Posted 2 days ago
Baldwin Inn & Suites, SureStay Collection by Best Western

Hotels near other Winchester Square attractions

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.
See properties

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?
See properties

Frequently asked questions

What's the area like around Winchester Square?
Winchester Square is located in Springfield. If you're looking for a convenient place to stay, take a look at the 16 hotels and other accommodation options you'll find within a mile.
What's the best hotel to stay close to Winchester Square?
MGM Springfield is one of the top choices for your stay based on our traveller data, and this hotel offers a casino and 8 restaurants. It's located 1.5 mi (2.4 km) from Winchester Square. Other good options within a few miles include La Quinta Inn & Suites by Wyndham Springfield MA and Holiday Inn Express Springfield Downtown by IHG.
How many hotels can I expect to find near Winchester Square?
Expedia has 16 hotels and other accommodation options within a mile from Winchester Square.
If I need to cancel the hotel reservation for my stay near Winchester Square, will I receive a refund?
Yes, most hotel reservations are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before check in. If you have a non-refundable reservation, you might be able to cancel it and get a refund within a 24-hour period of booking. Plug in your dates, click on "Search", then you can use the "fully refundable" filter to review the best deals available near Winchester Square.
What can I see and do near Winchester Square?
Springfield Armory, Springfield Science Museum and Connecticut Valley Historical Museum feature a variety of fascinating exhibits to see while you're in town. Springfield City Library, Paramount Theater and Storrowton Village Museum are monuments to see when you're exploring the area around Winchester Square. You can watch performances at CityStage Symphony Hall, Majestic Theatre and Appleton Auditorium if you're interested in local theatre.