Hotels near Winchester Square Springfield

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Where to stay near Winchester Square?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night near Winchester Square on Hotels.com. These hotels close to Winchester Square consistently deliver on quality, location and traveler experience. Last updated on October 9, 2026.

A breakfast area with a counter, seating, and a menu display.

A hotel room with a bed, a desk, a chair, a small table, and a window with a view of a building.

A Holiday Inn Express hotel with large windows, a prominent 'Holiday Inn Express' sign, and classical architectural columns.

A modern living room with a sofa, armchair, and a small table.

1. Holiday Inn Express Springfield Downtown by IHG

Metro Center, 2 km from Winchester Square

Taneisa

CNY670

CNY760 total

includes taxes & fees

Nov 9 - Nov 10

A bar area with wooden tables and chairs, a central bar counter with taps, and a brick wall with shelves of bottles and glasses.

A hotel room with two beds, a desk, a chair, a lamp, and a large window with curtains.

A rooftop terrace with round tables set for dining, overlooking a historic building with two prominent towers.

A modern hotel lobby with leather furniture, a bar area, and a large TV screen.

2. MGM Springfield

Metro Center, 2.3 km from Winchester Square

Mark

CNY999

CNY1,285 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with tiled flooring, metal railings, and multiple seating areas with chairs and tables.

A hotel reception area with a central counter, a sign reading "The Pavilion Pantry," and a wall with a quote.

A large, multi-story hotel with a prominent 'Hilton Garden Inn' sign, surrounded by well-maintained landscaping and a clear sky.

A spacious lobby with a large wooden table, leopard-print chairs, and modern pendant lighting.

3. Hilton Garden Inn-Springfield, MA

South End, 2.6 km from Winchester Square

Kerry

CNY849

CNY963 total

includes taxes & fees

Oct 21 - Oct 22

An indoor swimming pool with a pool lift, a changing room, and a view of the outside.

A reception area with a wooden reception desk, framed pictures on the wall, a small plant, and a hallway leading to an exit.

A spacious dining area with multiple tables and chairs, a sofa, and patterned curtains.

A hotel room with two beds, a desk with a flat-screen TV, a chair, and a bedside table with lamps.

4. Hampton Inn & Suites Springfield/Downtown

South End, 2.4 km from Winchester Square

Theresa

CNY792

CNY899 total

includes taxes & fees

Oct 25 - Oct 26

A multi-story hotel with a prominent 'La Quinta' sign, featuring a symmetrical facade with evenly spaced windows and a central entrance.

A spacious lobby with wooden flooring, a reception desk, and two patterned armchairs.

An indoor swimming pool with clear blue water, surrounded by chairs and a high ceiling with visible ductwork.

A hotel dining area with multiple tables and chairs, a patterned carpet, and a reception desk in the background.

5. La Quinta Inn & Suites by Wyndham Springfield MA

Metro Center, 2.5 km from Winchester Square

Leandro

CNY741

CNY840 total

includes taxes & fees

Nov 1 - Nov 2

An indoor swimming pool with clear glass ceilings, sunlit interior, and lounge chairs along the sides.

A room with three framed autumn tree paintings on the wall, two brown sofas with red and orange cushions, and a patterned carpet.

A restaurant with wooden tables and chairs, hanging pendant lights, and sports memorabilia on the walls.

A lobby with a reception desk, seating area, and artwork on the walls.

6. Sheraton Springfield Monarch Place Hotel

Metro Center, 2.5 km from Winchester Square

Gregory

CNY1,077

CNY1,225 total

includes taxes & fees

Oct 25 - Oct 26

A modern reception area with two reception desks, a seating area with armchairs and a sofa, and a large plant.

A modern lounge area with a central fire feature, comfortable seating, and a staircase in the background.

A spacious dining area with a large marble table and multiple chairs, a kitchen with wooden cabinets, and a modern ceiling light fixture.

A gym with various exercise equipment, large windows, and a view of buildings outside.

7. Marriott Springfield Downtown

Metro Center, 2.5 km from Winchester Square

Marissa

CNY970

CNY1,100 total

includes taxes & fees

Nov 1 - Nov 2

A modern lounge area with sofas, a pool table, and a unique chandelier.

A modern coffee bar with espresso machines, a coffee station, and a shelf with coffee products.

A hotel room with a large bed, two bedside tables with lamps, a massage chair, and a wall mural of mountains.

A modern hotel with a covered entrance, multiple windows, and a well-maintained lawn.

8. Blue A Modern Hotel, an Ascend Collection Hotel

6 km from Winchester Square

anita

CNY678

CNY776 total

includes taxes & fees

Nov 1 - Nov 2

An outdoor patio area with seating, a fire feature, and a view of the building's exterior.

A modern bar area with a long counter, multiple bar stools, and a wooden accent wall.

A modern reception area with a wooden reception desk, seating area with sofas and chairs, and large windows providing natural light.

A hotel room with two beds, a large window with a view of trees, and a wall mural.

9. Courtyard by Marriott West Springfield

5.4 km from Winchester Square

CNY879

CNY1,006 total

includes taxes & fees

Nov 1 - Nov 2

A bedroom with a bed, a nightstand, a lamp, and a window with curtains.

A cozy room with a bed, breakfast area, and a wall with Alice in Wonderland-themed decor.

A two-story house with a front porch, a number 20 sign, and a pathway leading to the entrance.

A living room with two armchairs, a coffee table, a lamp, a mirror, and a chandelier.

10. Naomi's Inn Bed & Breakfast

Liberty Heights, 3.6 km from Winchester Square

Susan

CNY704

CNY799 total

includes taxes & fees

Oct 20 - Oct 21

A breakfast area with a waffle station, coffee machine, and various food options.

A modern hotel room with a large bed, a desk, and a chair.

A modern hotel room with a flat-screen TV on a wooden desk, a blue office chair, and a large window with abstract art.

11. Tru by Hilton Chicopee Springfield

6.8 km from Winchester Square

Tammy

CNY735

CNY834 total

includes taxes & fees

Nov 1 - Nov 2

A hot tub with a tiled edge and a metal ladder, surrounded by large windows with a view of a parking lot and trees.

A Hampton Inn hotel with a modern facade, multiple floors, and a well-lit entrance.

A hotel lobby with a wooden reception desk, comfortable seating, a fireplace, and a television.

A gym with treadmills, elliptical machines, and a bench.

12. Hampton Inn Springfield South Enfield

13.7 km from Winchester Square

CNY912

CNY1,049 total

includes taxes & fees

Oct 30 - Oct 31

A spacious lobby with a fireplace, comfortable seating, and a view of the outdoors.

A hotel room with a flat-screen TV mounted on the wall, a dining table with chairs, a sofa, and a small ottoman.

A compact kitchen with wooden cabinets, a white refrigerator, a microwave, a coffee maker, and a sink. There are two bar stools at the island.

An indoor swimming pool with clear lane markings, a lifeguard chair, and a pool ladder.

13. Holiday Inn Express Ludlow by IHG

9.1 km from Winchester Square

Helen

CNY764

CNY854 total

includes taxes & fees

Nov 8 - Nov 9

A Fairfield Inn & Suites by Marriott hotel with a modern design, a covered entrance, and landscaped areas.

A spacious lobby with a reception desk, a blue decorative wall, and a wooden floor.

A hotel lobby with a seating area, a bar, and a TV screen.

A hotel lobby with a reception desk, seating area, and large windows.

14. Fairfield Inn & Suites Springfield Holyoke

9.5 km from Winchester Square

erin

CNY877

CNY980 total

includes taxes & fees

Nov 9 - Nov 10

A patio area with a stone fire pit, wicker furniture, and a view of the building's interior.

A spacious lobby with comfortable seating, a fireplace, and large windows.

A spacious hotel lobby with a high ceiling, a fireplace, seating areas, and a large TV screen.

An indoor swimming pool with clear blue water, surrounded by lounge chairs and umbrellas.

15. Residence Inn Springfield Chicopee

6.9 km from Winchester Square

Jason

CNY1,134

CNY1,286 total

includes taxes & fees

Oct 18 - Oct 19

A multi-story hotel with a modern facade, large windows, and a well-lit entrance.

A hotel room with a bed, a desk, a chair, a TV, and a window with curtains.

A hotel room with a dining area, a sofa, a TV, and a kitchen area with a stove.

A hotel lobby with a reception desk, two sofas, a coffee table, a TV, and artwork on the walls.

16. Candlewood Suites West Springfield by IHG

5.2 km from Winchester Square

CNY697

CNY798 total

includes taxes & fees

Oct 18 - Oct 19

A hotel entrance with a covered patio, a garden with colorful flowers, and a clear sky.

An indoor swimming pool with tiled flooring, a blue ceiling, and seating areas with tables and chairs.

A hotel with a well-maintained garden and a sign indicating it is a Homewood Suites by Hilton.

A buffet setup with various food options, a microwave, and a coffee station.

17. Homewood Suites by Hilton Holyoke-Springfield/North

9.1 km from Winchester Square

Kristen

CNY984

CNY1,100 total

includes taxes & fees

Oct 25 - Oct 26

A Best Western hotel with a modern design, featuring a large building with multiple windows and a well-lit entrance.

A hotel room with two beds, a desk with a computer, a TV, and a window with curtains.

A restaurant with a counter, seating area, and various food and drink dispensers.

A gym with treadmills, elliptical machines, and weight benches.

18. Best Western Springfield West Inn

5 km from Winchester Square

Mary

CNY655

CNY750 total

includes taxes & fees

Oct 18 - Oct 19

A small bathroom with a white sink, a mirror, and a black cabinet.

A reception area with a counter, two chairs, a small table, and a window.

A motel with a prominent '6' sign, a brick entrance, and a parking area with a white SUV.

A hotel room with a bed, a window with curtains, a wall-mounted air conditioner, and a nightstand with a lamp.

19. Motel 6 Enfield, CT - Hartford

13.4 km from Winchester Square

Andrea

CNY393

CNY452 total

includes taxes & fees

Oct 11 - Oct 12

A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

A modern hotel with a sign reading "Baldwin Inn & Suites," featuring a large entrance and a parking lot.

A compact kitchen with a stainless steel refrigerator, microwave, and dishwasher, wooden cabinets, and a marble countertop.

A hotel room with a dining area, a living room with a sofa and armchairs, a coffee machine, and a plant.

20. Baldwin Inn & Suites, SureStay Collection by Best Western

4.7 km from Winchester Square

Everton

CNY742

CNY849 total

includes taxes & fees

Oct 20 - Oct 21

View all properties

Compare popular hotels close to Winchester Square

Property	Property class	Guest rating
Holiday Inn Express Springfield Downtown by IHG	9.0 Wonderful 1,323 reviews	View
MGM Springfield	9.0 Wonderful 1,543 reviews	View
Hilton Garden Inn-Springfield, MA	8.6 Excellent 1,007 reviews	View
Hampton Inn & Suites Springfield/Downtown	8.6 Excellent 1,004 reviews	View
La Quinta Inn & Suites by Wyndham Springfield MA	8.0 Very good 1,243 reviews	View

Other landmarks near Winchester Square

Mason Square Branch Springfield City Library

Mason Square Branch Springfield City Library is worth a pic or two when discovering Old Hill.

See properties

Pendleton Ave. Park

Pendleton Ave. Park is worth a pic or two when discovering Old Hill.

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Samuel A. Bolden Park

Samuel A. Bolden Park is worth a visit, located 1.5 mi (2.4 km) from central Springfield.

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Gunn Square Park

Gunn Square Park is worth a visit, located 1.6 mi (2.5 km) from central Springfield.

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Karen Sprague Cultural Arts Center

Karen Sprague Cultural Arts Center is 1.8 mi (2.9 km) from central Springfield, why not stop by during your stay. If you have fun at Karen Sprague Cultural Arts Center, you'll love Springfield Science Museum and Springfield Museums, both located nearby.

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Magazine Playground

Magazine Playground is worth a pic or two when discovering McKnight.

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Thompson Triangle

Thompson Triangle is worth a pic or two when discovering McKnight.

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Barrows Playgound

Barrows Playgound is worth a pic or two when discovering Old Hill.

See properties

Frequently Asked Questions

What are the best hotels near Winchester Square?

Guests love staying at MGM Springfield, which is a hotel near Winchester Square.
Another highly rated hotel is Marriott Springfield Downtown, which is a short drive away.
You'll find 965 hotels, vacation rentals, and more lodging options to choose from in the surrounding area.

How much does it cost to stay in a hotel near Winchester Square?

On Hotels.com, you can find the best options for your travel budget by entering your search criteria and sorting by price. Remember that pricing varies based on where and when you plan to go.

Search for the lowest price per night from CNY393

What cheap hotels are close to Winchester Square?

Quality Inn West Springfield is a budget-friendly hotel near Winchester Square and offers a free buffet breakfast, free parking, and free in-room WiFi.
Another low-cost alternative is D. Hotel Suites & Spa, which is 21 minutes away by car.

Can I find hotels close to Winchester Square that are fully refundable?

Yes, there are many hotels with refundable room rates, but be sure to check the cancellation deadline. Find refundable rates using the "Fully refundable" filter when you search for hotels.

A couple of highly rated hotels near Winchester Square that offer these rates are MGM Springfield and Marriott Springfield Downtown.

What are the best romantic hotels near Winchester Square?

If you are looking for a romantic stay, Sheraton Springfield Monarch Place Hotel offers 2 restaurants, an indoor pool, and a bar/lounge. It's a short 4-minute drive from Winchester Square.
Another great option is Marriott Hartford Downtown, which is 37 minutes away by car.

What are the best hotels close to Winchester Square with free breakfast?

Start your day nourished with a free full breakfast at Naomi's Inn Bed & Breakfast, which is a short 6-minute drive from Winchester Square.
Simsbury 1820 House is also a recommended place to stay with a free continental breakfast, and it's located in the larger area.

Which hotels near Winchester Square have rooms with great views?

Travelers can enjoy rooms with city views at Marriott Springfield Downtown, which is a short 4-minute drive from Winchester Square.
Also recommended is Sheraton Springfield Monarch Place Hotel, which has rooms with river or city views.

What are the best family hotels close to Winchester Square?

For travelers looking for a family-friendly stay, La Quinta Inn & Suites by Wyndham Springfield MA offers free cribs, an indoor pool, and an arcade/game room. Winchester Square is a short drive away.
Another great option for your family's trip is Sheraton Springfield Monarch Place Hotel.

What are the best luxury hotels near Winchester Square?

Indulge yourself when you stay at Rock Hall Luxe Lodging, which is within reach of Winchester Square and offers an outdoor pool, a hot tub, and an outdoor tennis court.

What are the best hotels near Winchester Square with free parking?

Travelers looking to drive and park with ease should consider a stay at MGM Springfield, which offers free parking. You'll be a short 4-minute drive from Winchester Square.
Another property that offers free parking is Naomi's Inn Bed & Breakfast, which is a short drive away.

What are the best hotels near Winchester Square with a pool?

If swimming is at the top of your list, MGM Springfield has a seasonal outdoor pool. Winchester Square is a short 4-minute drive from the hotel.
Another great choice for a hotel with a pool is Marriott Springfield Downtown.

What cheap motels can I book close to Winchester Square?

To save on your stay near Winchester Square, take a look at Red Carpet Inn West Springfield, which offers a seasonal outdoor pool and a free continental breakfast.
Riverdale Inn is another affordable motel to consider in the area.

What are the best things to see and do around my hotel near Winchester Square?

Other attractions near Winchester Square include Six Flags New England, Naismith Memorial Basketball Hall of Fame, and Eastern States Exposition.
Holyoke Mall, Springfield Museums, and Olympia Ice Center are other places to visit in the area.

What are the best pet-friendly hotels close to Winchester Square?

Bring your cherished pet with you to MGM Springfield, which is a short 4-minute drive from Winchester Square.
A second pet-friendly hotel is Sheraton Springfield Monarch Place Hotel.