Top 10 Hotels Near Winchester Square in Springfield for 2026

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

Tomorrow

This weekend

Next weekend

Our top choices for Winchester Square hotels

A hotel lobby with reception desks, seating area, and a modern ceiling design.

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

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

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

1. Holiday Inn Express Springfield Downtown by IHG

Metro Center, 2 km from Winchester Square

Heidi

RM393

RM446 total

includes taxes & fees

23 Nov - 24 Nov

A cozy, well-lit lounge area with a bar, comfortable seating, and a visible staircase leading to an upper level.

A casino with multiple blackjack tables, slot machines, and a large chandelier.

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

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

Carla

RM608

RM782 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

3. Hampton Inn & Suites Springfield/Downtown

South End, 2.4 km from Winchester Square

James

RM430

RM488 total

includes taxes & fees

8 Nov - 9 Nov

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

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.

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

4. La Quinta Inn & Suites by Wyndham Springfield MA

Metro Center, 2.5 km from Winchester Square

Heather

RM444

RM504 total

includes taxes & fees

15 Nov - 16 Nov

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

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

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

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

5. Marriott Springfield Downtown

Metro Center, 2.5 km from Winchester Square

Nataliya

RM552

RM626 total

includes taxes & fees

1 Nov - 2 Nov

A two-story white house with a green door, white picket fence, and white flowering bushes.

A fireplace with a tiled surround, a mirror above it, and decorative plates on the wall.

A dining room with a wooden table, chairs, a chandelier, and a floral wallpaper pattern.

A four-poster bed with a floral bedspread, bedside tables with lamps, a mirror on the wall, and a window with curtains.

6. Daniel Stebbins House

16.8 km from Winchester Square

David

RM1,103

RM1,232 total

includes taxes & fees

1 Nov - 2 Nov

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

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

An indoor swimming pool with clear signage, a no diving policy, and a seating area with chairs and a table.

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

7. Fairfield Inn & Suites Springfield Holyoke

9.5 km from Winchester Square

Caroline

RM517

RM578 total

includes taxes & fees

16 Nov - 17 Nov

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

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

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

A modern hotel lobby with blue sofas, a bar area, and a decorative chandelier.

8. Blue A Modern Hotel, an Ascend Collection Hotel

6 km from Winchester Square

Samantha

RM413

RM472 total

includes taxes & fees

16 Nov - 17 Nov

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

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

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

A snack display with various chips and snacks, a refrigerated display with beverages, and a cooler with bottled water.

9. Hampton Inn Springfield South Enfield

13.7 km from Winchester Square

kelly

RM559

RM643 total

includes taxes & fees

22 Nov - 23 Nov

A swimming pool with a blue interior, surrounded by red chairs and a green bench.

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

A room with a foosball table, a sofa, and a wall with various attractions listed.

10. Tru by Hilton Chicopee Springfield

6.8 km from Winchester Square

Gary

RM447

RM508 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

11. Holiday Inn Express Ludlow by IHG

9.1 km from Winchester Square

Erin

RM433

RM483 total

includes taxes & fees

22 Nov - 23 Nov

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 residential garden with a lawn, a variety of plants, and a pathway.

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

12. Naomi's Inn Bed & Breakfast

Liberty Heights, 3.6 km from Winchester Square

Peter

RM428

RM486 total

includes taxes & fees

28 Oct - 29 Oct

A bedroom with a four-poster bed, a leather sofa, a wooden coffee table, and a view of greenery through the window.

A hotel with a sign reading "D. HOTEL & SUITES" on the facade.

An outdoor patio with white chairs and tables, a central fire feature, and string lights.

A bar area with a wooden counter, bar stools, and a variety of bottles and glasses.

13. D. Hotel Suites & Spa

18.5 km from Winchester Square

Devon

RM496

RM581 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A spacious hotel dining area with multiple tables and chairs, a kitchen area, and a high ceiling with natural light.

A gym with weightlifting equipment, a bench, and a wall-mounted dumbbell rack.

14. Homewood Suites by Hilton Holyoke-Springfield/North

9.1 km from Winchester Square

Andrew

RM700

RM782 total

includes taxes & fees

22 Nov - 23 Nov

A hotel lobby with a reception desk, seating area, and a dining section.

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

A modern dining area with tables and chairs, a patterned carpet, and a wall-mounted TV.

A gym with treadmills, an elliptical, a stationary bike, and a bench press.

15. Hampton Inn Westfield

14.1 km from Winchester Square

Shaleen

RM482

RM539 total

includes taxes & fees

17 Nov - 18 Nov

An outdoor patio area with a stone fire pit, seating, and a grill.

A spacious conference room with a high ceiling, large windows, and a variety of seating arrangements including sofas, chairs, and a round table.

A hotel room with a kitchenette, a sofa, a desk, and a TV.

A hotel room with a sofa, TV, fireplace, bed, and a small table with bar stools.

16. Residence Inn by Marriott West Springfield

6.1 km from Winchester Square

Keisha

RM547

RM626 total

includes taxes & fees

1 Nov - 2 Nov

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.

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

17. Motel 6 Enfield, CT - Hartford

13.4 km from Winchester Square

John

RM225

RM259 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, a bathroom with a bathtub, a television, and a microwave.

A landscaped garden area with mulch, shrubs, and a concrete pathway.

A bathroom with a large bathtub, a microwave, and a potted plant.

A small, well-lit room with a kitchenette, a water dispenser, a coffee machine, and a variety of books on a shelf.

18. Wilbraham Inn

8.4 km from Winchester Square

Jeanine

RM526

RM577 total

includes taxes & fees

25 Oct - 26 Oct

An indoor swimming pool with blue walls, large windows, and several lounge chairs.

A modern hotel lobby with a dining area, seating, and a TV screen on the wall.

A snack display with various packaged foods and a microwave.

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

19. Hampton Inn Chicopee/Springfield

7.1 km from Winchester Square

Melissa

RM442

RM501 total

includes taxes & fees

17 Nov - 18 Nov

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

A hotel lobby with a brown sofa, a reception desk, a wall-mounted TV, and a large plant.

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

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

20. Best Western Springfield West Inn

5 km from Winchester Square

Susan

RM399

RM457 total

includes taxes & fees

29 Oct - 30 Oct

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 1,340 reviews	View
MGM Springfield	9.0 Wonderful 1,542 reviews	View
Hampton Inn & Suites Springfield/Downtown	8.6 Excellent 1,002 reviews	View
La Quinta Inn & Suites by Wyndham Springfield MA	8.0 Very good 1,247 reviews	View
Marriott Springfield Downtown	8.0 Very good 1,001 reviews	View

Top Winchester Square Hotel Reviews

Courtyard by Marriott West Springfield

10/10 Excellent

"great staff"

Holiday Inn Express Springfield Downtown by IHG

8/10 Good

"It was fine."

Tru by Hilton Chicopee Springfield

10/10 Excellent

"The first thing I noticed was how nice and helpful the staff was. Everyone was very friendly and quick to offer assistance. The hotel itself and our room were very clean and well maintained and the breakfast was delicious. I plan to stay here whenever we are in the area."

Hilton Garden Inn-Springfield, MA

10/10 Excellent

"Great local right next to the basketball hall of fame"

Comfort Inn & Suites West Springfield

10/10 Excellent

"The staff was exceptionally friendly and helpful throughout our stay. They provided clear information about the hotel and its amenities, including Wi-Fi access, and promptly assisted us in resolving an issue with our key card. Each evening, the common areas tended to be quite noisy, with children frequently running through the hallways. It was also common to see kids moving back and forth between the fitness center and pool area, leaving the floors wet and slippery, which made using either amenity less enjoyable. In our room, the bathroom sink drained very slowly due to a clog. The shower also dripped continuously, with the water striking the metal drain cover and creating a persistent noise. To make it more tolerable, we lifted the drain cover so the water would drip directly onto the porcelain surface and kept the bathroom door closed to help reduce the sound."

Hampton Inn West Springfield

10/10 Excellent

"."

Candlewood Suites West Springfield by IHG

10/10 Excellent

"COMFORTABLE ROOMS ACCOMMODATING STAFF STAY HERE OFTEN"

Other attractions near Winchester Square

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

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.

See properties

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.

See properties

Karen Sprague Cultural Arts Center

Enjoy an outing to Karen Sprague Cultural Arts Center during your stay in Springfield. Attend a basketball game or visit the shops in this family-friendly area.

See properties

Magazine Playground

After visiting Magazine Playground, make a plan to see the other sights and activities in Springfield.

See properties

Thompson Triangle

After visiting Thompson Triangle, make a plan to see the other sights and activities in Springfield.

See properties

Barrows Playgound

After visiting Barrows Playgound, make a plan to see the other sights and activities in Springfield.

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 18 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 1.4 mi (2.3 km) from Winchester Square. Other good options within a few miles include Holiday Inn Express Springfield Downtown by IHG and La Quinta Inn & Suites by Wyndham Springfield MA.

How many hotels can I expect to find near Winchester Square?

Expedia has 18 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 Naismith Memorial Basketball Hall of Fame feature a variety of fascinating exhibits to see while you're in town. Paramount Theater, Storrowton Village Museum and Springfield City Library are monuments to see when you're exploring the area around Winchester Square. You can watch performances at Majestic Theatre, CityStage Symphony Hall and Appleton Auditorium if you're interested in local theatre.

Hotels near Winchester Square

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winchester Square hotels

1. Holiday Inn Express Springfield Downtown by IHG

2. MGM Springfield

3. Hampton Inn & Suites Springfield/Downtown

4. La Quinta Inn & Suites by Wyndham Springfield MA

5. Marriott Springfield Downtown

6. Daniel Stebbins House

7. Fairfield Inn & Suites Springfield Holyoke

8. Blue A Modern Hotel, an Ascend Collection Hotel

9. Hampton Inn Springfield South Enfield

10. Tru by Hilton Chicopee Springfield

11. Holiday Inn Express Ludlow by IHG

12. Naomi's Inn Bed & Breakfast

13. D. Hotel Suites & Spa

14. Homewood Suites by Hilton Holyoke-Springfield/North

15. Hampton Inn Westfield

16. Residence Inn by Marriott West Springfield

17. Motel 6 Enfield, CT - Hartford

18. Wilbraham Inn

19. Hampton Inn Chicopee/Springfield

20. Best Western Springfield West Inn

Compare popular hotels close to Winchester Square

Top Winchester Square Hotel Reviews

Courtyard by Marriott West Springfield

Holiday Inn Express Springfield Downtown by IHG

Tru by Hilton Chicopee Springfield

Hilton Garden Inn-Springfield, MA

Comfort Inn & Suites West Springfield

Hampton Inn West Springfield

Candlewood Suites West Springfield by IHG

Other attractions near Winchester Square

Mason Square Branch Springfield City Library

Pendleton Ave. Park

Samuel A. Bolden Park

Gunn Square Park

Karen Sprague Cultural Arts Center

Magazine Playground

Thompson Triangle

Barrows Playgound

Frequently asked questions