The Best Hotels Closest to Winchester Square in Springfield for 2026

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Our top choices for Winchester Square hotels

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

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

Casey

AED 459

AED 521 total

includes taxes & fees

21 Oct - 22 Oct

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

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.

2. MGM Springfield

Metro Center, 2.3 km from Winchester Square

Tiffany

AED 559

AED 717 total

includes taxes & fees

18 Oct - 19 Oct

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

A modern gym with treadmills, an elliptical, and a rowing machine. There are dumbbells and a red exercise ball.

3. Hilton Garden Inn-Springfield, MA

South End, 2.6 km from Winchester Square

Richard

AED 449

AED 509 total

includes taxes & fees

21 Oct - 22 Oct

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

A narrow hallway with two beverage dispensers and a snack shelf.

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

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

Claire

AED 426

AED 484 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

5. La Quinta Inn & Suites by Wyndham Springfield MA

Metro Center, 2.5 km from Winchester Square

Heather

AED 450

AED 510 total

includes taxes & fees

1 Oct - 2 Oct

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

A multi-level hotel lobby with a central staircase, decorative murals, and a chandelier.

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

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

Shellann

AED 591

AED 673 total

includes taxes & fees

6 Oct - 7 Oct

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 modern hotel lobby with a bar area, seating arrangements, and a staircase.

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

7. Marriott Springfield Downtown

Metro Center, 2.5 km from Winchester Square

Juan

AED 598

AED 679 total

includes taxes & fees

25 Oct - 26 Oct

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

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

8. Daniel Stebbins House

16.8 km from Winchester Square

David

AED 993

AED 1,109 total

includes taxes & fees

30 Sep - 1 Oct

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

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

A hotel exterior with a sign reading "Residence Inn Marriott."

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

9. Residence Inn Springfield Chicopee

6.9 km from Winchester Square

Ronald

AED 621

AED 705 total

includes taxes & fees

18 Oct - 19 Oct

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

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

10. Blue A Modern Hotel, an Ascend Collection Hotel

6 km from Winchester Square

Charles

AED 372

AED 425 total

includes taxes & fees

25 Oct - 26 Oct

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

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

11. Courtyard by Marriott West Springfield

5.4 km from Winchester Square

Amy

AED 496

AED 568 total

includes taxes & fees

4 Oct - 5 Oct

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 gym with treadmills, elliptical machines, and a bench.

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.

12. Hampton Inn Springfield South Enfield

13.7 km from Winchester Square

Selina

AED 569

AED 655 total

includes taxes & fees

12 Oct - 13 Oct

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

A hotel room with a kitchenette, a bed, a TV, a desk, and a dining area.

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

Erin

AED 448

AED 501 total

includes taxes & fees

29 Oct - 30 Oct

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

A modern hotel lobby with a seating area featuring three cushioned benches and two small tables.

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

An indoor swimming pool with a clear waterline, a metal ladder, and red chairs around the pool area.

14. Tru by Hilton Chicopee Springfield

6.8 km from Winchester Square

SASHAWN

AED 449

AED 509 total

includes taxes & fees

25 Oct - 26 Oct

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.

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

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

15. Fairfield Inn & Suites Springfield Holyoke

9.5 km from Winchester Square

MONA

AED 481

AED 537 total

includes taxes & fees

19 Oct - 20 Oct

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.

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.

16. D. Hotel Suites & Spa

18.5 km from Winchester Square

Karen

AED 447

AED 523 total

includes taxes & fees

4 Oct - 5 Oct

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

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.

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

17. Naomi's Inn Bed & Breakfast

Liberty Heights, 3.6 km from Winchester Square

Peter

AED 386

AED 438 total

includes taxes & fees

4 Oct - 5 Oct

A modern dining area with a long table, cushioned seating, and framed artwork on the wall.

A hotel conference room with round tables, chairs, and floral centerpieces.

An outdoor patio area with a pergola, seating, and a barbecue station.

A compact kitchen with white cabinets, a microwave, a dishwasher, a sink, and a coffee machine.

18. Homewood Suites by Hilton Holyoke-Springfield/North

9.1 km from Winchester Square

Andrew

AED 539

AED 602 total

includes taxes & fees

18 Oct - 19 Oct

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

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

A hotel room with a large bed, bedside lamps, a desk, and a TV.

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

19. Residence Inn by Marriott West Springfield

6.1 km from Winchester Square

Joseph

AED 492

AED 563 total

includes taxes & fees

8 Oct - 9 Oct

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

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.

A swimming pool with a blue interior, surrounded by lounge chairs and a tiled floor.

20. Candlewood Suites West Springfield by IHG

5.2 km from Winchester Square

Jon

AED 367

AED 420 total

includes taxes & fees

18 Oct - 19 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 1,310 reviews	View
MGM Springfield	9.0 Wonderful 1,551 reviews	View
Hilton Garden Inn-Springfield, MA	8.6 Excellent 1,004 reviews	View
Hampton Inn & Suites Springfield/Downtown	8.6 Excellent 1,000 reviews	View
La Quinta Inn & Suites by Wyndham Springfield MA	8.0 Very good 1,254 reviews	View

Top Winchester Square Hotel Reviews

Blue A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent

"The staff was great and everything was very clean."

Quality Inn West Springfield

8/10 Good

"Very nice. We stay here every year. Would like to see the breakfast hours available until 10:00. Thank you"

Holiday Inn Express Springfield Downtown by IHG

10/10 Excellent

"Overall: Clean, safe, nice, and would stay again if I needed to be in Springfield. I originally planned on staying one night, but had a family emergency that meant I needed to come to town a day early. I wasn't able to change the dates of my original booking to lengthen my stay, so I just booked another night separately. I worried that I'd have to check out and back in because I had two different bookings, but the front desk staff was able to handle it as one booking and keep me in the same room both nights (so convenient!) The hotel's location was good--close to the casino and nearby restaurants, walkable to and from the bus station. The hotel was clean and comfortable, and very much fit the bill of what I needed in Springfield. I would stay here again."

Hampton Inn & Suites Springfield/Downtown

8/10 Good

"Nice Size Room. Property was Well Maintained & Being Upgraded."

MGM Springfield

10/10 Excellent

"Great place to stay!"

Red Roof Inn PLUS+ West Springfield

8/10 Good

"It was very adequate with basics. There was no hair blower. There are not many good places to walk to"

Howard Johnson by Wyndham Springfield

10/10 Excellent

"The property was good Clean room Efficient staff- towels and beds made- much appreciated"

Best Western Springfield West Inn

8/10 Good

"The staff were nice. The vending machine was out of order. The Ice machine was old and it tasted a little weird. Breakfast has its own room and is small so sitting in there is a little uncomfortable but, it’s not very fresh. The yogurt tasted sour. There is a waffle maker so thats a plus. There was no chain or latch for the doo just the lock. The sink is out in the open and separate from the bathroom which is annoying if you’re not by yourself. If you’re staying here for proximity for the BIG E, it is a close RIDE NOT WALK. Unfortunately its listed as 10 minute walk which is not true its a 10 minute drive. The walls are kind of paper thin so yes you can hear that elevator ding. This is located on a a very busy highway like street so if you need something quick and decide to walk its like 20 minutes down. Be prepared for a lot of U turns to get to the other side of the road. Also if you’re going for the BIG E be prepared for your uber rides to not want to take you all the way there to memorial drive in fear of getting stuck in traffic. You will hear a lot of huffing and puffing. Try putting the location to Friendly’s on 19 Springfield Street and just walk down. Saves you the trouble. Overall location is great, building is old, staff is working with what they got, not terrible, not amazing, but works for budget."

Riverdale Inn

10/10 Excellent

"Great service and clean room and good attendance"

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.

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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?

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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.

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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? Check out the shops and top-notch restaurants in this family-friendly area.

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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.

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Magazine Playground

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

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Thompson Triangle

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

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Barrows Playgound

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

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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, check out the 18 hotels and other accommodations you'll find within a mile.

What's the best place to stay close to Winchester Square?

MGM Springfield is one of the top choices for your stay based on our traveler data, and this hotel offers a casino and 8 restaurants. It's located 1.4 mi (2.3 km) from Winchester Square. Other good choices within 5 miles include Holiday Inn Express Springfield Downtown by IHG and La Quinta Inn & Suites by Wyndham Springfield MA.

How many hotels will I be able to find near Winchester Square?

Expedia has 18 hotels and other accommodations 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! The majority of hotel room reservations are fully refundable as long as you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of check in. If your reservation is non-refundable, you might be able to cancel it and get a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to get the best deals near Winchester Square.

Where can I learn more about changing or cancelling my trip in the area near Winchester Square?

For more information about picking new dates or cancelling your stay near Winchester Square, go to https://www.expedia.com/service/.

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 theater.

Find hotels near Winchester Square, Springfield from AED 420

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Treat yourself

Be picky

Check prices for these dates

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Our top choices for Winchester Square hotels

1. Holiday Inn Express Springfield Downtown by IHG

2. MGM Springfield

3. Hilton Garden Inn-Springfield, MA

4. Hampton Inn & Suites Springfield/Downtown

5. La Quinta Inn & Suites by Wyndham Springfield MA

6. Sheraton Springfield Monarch Place Hotel

7. Marriott Springfield Downtown

8. Daniel Stebbins House

9. Residence Inn Springfield Chicopee

10. Blue A Modern Hotel, an Ascend Collection Hotel

11. Courtyard by Marriott West Springfield

12. Hampton Inn Springfield South Enfield

13. Holiday Inn Express Ludlow by IHG

14. Tru by Hilton Chicopee Springfield

15. Fairfield Inn & Suites Springfield Holyoke

16. D. Hotel Suites & Spa

17. Naomi's Inn Bed & Breakfast

18. Homewood Suites by Hilton Holyoke-Springfield/North

19. Residence Inn by Marriott West Springfield

20. Candlewood Suites West Springfield by IHG

Compare popular hotels close to Winchester Square

Top Winchester Square Hotel Reviews

Blue A Modern Hotel, an Ascend Collection Hotel

Quality Inn West Springfield

Holiday Inn Express Springfield Downtown by IHG

Hampton Inn & Suites Springfield/Downtown

MGM Springfield

Red Roof Inn PLUS+ West Springfield

Howard Johnson by Wyndham Springfield

Best Western Springfield West Inn

Riverdale Inn

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