Springfield Hotel Guide - Winchester Square hotels in Springfield, United States of America.

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
21 Dec - 22 Dec
Tomorrow
22 Dec - 23 Dec
Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan

Filter by

Guest rating
Guest rating
Star rating

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, (1081)
"Great stay"
United States
Desiree
The price is €110
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, (1455)
"Loved the decor, very clean and comfortable "
United States
Lisa
The price is €164
includes taxes & fees
4 Jan - 5 Jan 2026
MGM Springfield
Lobby
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
8.4 out of 10, Very good, (1001)
"Great place to stay!"
United States
Craig
The price is €114
includes taxes & fees
27 Dec - 28 Dec
Hilton Garden Inn-Springfield, MA
Meeting facility
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, (991)
"It was nice and updated. Staff was amazing. "
United States
Awildo
The price is €126
includes taxes & fees
25 Dec - 26 Dec
Marriott Springfield Downtown
Property amenity
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, (1000)
"Breakfast was the best, friendly staff!!"
United States
Carla
The price is €140
includes taxes & fees
28 Dec - 29 Dec
Sheraton Springfield Monarch Place Hotel
Indoor pool
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, (1309)
"Eceryone was great but kudos to front desk Isha and Manager Greg who went above and beyond to make my stay enjoyable"
United States
Toni-Ann
The price is €107
includes taxes & fees
23 Dec - 24 Dec
La Quinta Inn & Suites by Wyndham Springfield MA
Room (Louis XIV)
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, (424)
"Artful and inspiring interior decorating and delicious French toast for breakfast!"
United States
Marielle
The price is €103
includes taxes & fees
22 Dec - 23 Dec
Naomi's Inn Bed & Breakfast
Flat-screen TV, fireplace
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 €416
includes taxes & fees
22 Dec - 23 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, (1002)
"Great like always "
United States
Sharee
The price is €83
includes taxes & fees
28 Dec - 29 Dec
Red Roof Inn PLUS+ West 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, (585)
"Quiet, convenient… a bit pricey "
United States
Mihai
The price is €115
includes taxes & fees
24 Dec - 25 Dec
Courtyard by Marriott 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 €75
includes taxes & fees
23 Dec - 24 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, (1000)
"Room was clean the people were nice easy check in it was very quiet "
United States
Christopher
The price is €88
includes taxes & fees
22 Dec - 23 Dec
Howard Johnson by Wyndham 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, (109)
"Great staff super nice beautiful hotel lots of parking "
United States
Yovelys
The price is €115
includes taxes & fees
11 Jan - 12 Jan 2026
Blue – A Modern Hotel, an Ascend Collection Hotel
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 €90
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, (809)
"Great staff"
United States
JOHN
The price is €96
includes taxes & fees
1 Jan - 2 Jan 2026
Candlewood Suites West Springfield by IHG
Exterior
Riverdale Inn

Riverdale Inn

Riverdale Inn
2.0 star property
6.5 km from Winchester Square
5.8 out of 10, (999)
"Staff was nice"
United States
Amanda
The price is €72
includes taxes & fees
22 Dec - 23 Dec
Riverdale Inn
Lobby
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, (1000)
"Decent breakfast"
United States
Jennifer
The price is €91
includes taxes & fees
27 Dec - 28 Dec
Best Western Springfield West Inn
Reception
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 €99
includes taxes & fees
28 Dec - 29 Dec
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, (1000)
"nearby eateries"
United States
Majorie
The price is €95
includes taxes & fees
25 Dec - 26 Dec
Hampton Inn West Springfield
Exterior
Residence Inn by Marriott West Springfield

Residence Inn by Marriott West Springfield

Residence Inn by Marriott West Springfield
3.0 star property
6.1 km from Winchester Square
8.6 out of 10, Excellent, (526)
"Yes, very clean room and staff was great "
United States
Nicolas
The price is €122
includes taxes & fees
28 Dec - 29 Dec
Residence Inn by Marriott 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

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.