The Best Hotels Closest to Winchester Square in Springfield for 2026

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Our top choices for Winchester Square hotels

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

1. MGM Springfield

Metro Center, 2.3 km from Winchester Square

Carla

₩198,885

₩255,922 total

includes taxes & fees

Nov 8 - Nov 9

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

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

2. Hampton Inn & Suites Springfield/Downtown

South End, 2.4 km from Winchester Square

James

₩153,848

₩174,540 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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

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

₩169,052

₩191,790 total

includes taxes & fees

Oct 21 - Oct 22

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

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

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

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

₩147,495

₩167,333 total

includes taxes & fees

Nov 8 - Nov 9

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

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

5. Sheraton Springfield Monarch Place Hotel

Metro Center, 2.5 km from Winchester Square

Brittany

₩214,903

₩244,475 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 spacious dining area with a large marble table and multiple chairs, a kitchen with wooden cabinets, and a modern ceiling light fixture.

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

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

6. Marriott Springfield Downtown

Metro Center, 2.5 km from Winchester Square

Juan

₩193,922

₩220,004 total

includes taxes & fees

Nov 1 - Nov 2

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

A garden with pink flowers and green foliage.

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

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

7. Daniel Stebbins House

16.8 km from Winchester Square

David

₩360,730

₩402,936 total

includes taxes & fees

Oct 19 - Oct 20

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

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

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

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

8. Residence Inn Springfield Chicopee

6.9 km from Winchester Square

Ronald

₩225,781

₩256,148 total

includes taxes & fees

Oct 22 - Oct 23

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

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

9. Blue A Modern Hotel, an Ascend Collection Hotel

6 km from Winchester Square

Charles

₩142,957

₩163,614 total

includes taxes & fees

Oct 25 - Oct 26

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

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

A modern bar area with a long counter, multiple screens, and a seating area with metal chairs.

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

10. Courtyard by Marriott West Springfield

5.4 km from Winchester Square

Amy

₩175,748

₩201,143 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 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.

11. Hampton Inn Springfield South Enfield

13.7 km from Winchester Square

Jessica

₩181,533

₩208,763 total

includes taxes & fees

Oct 30 - Oct 31

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 kitchenette, a bed, a TV, a desk, and a dining area.

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

12. Holiday Inn Express Ludlow by IHG

9.1 km from Winchester Square

Erin

₩156,172

₩174,445 total

includes taxes & fees

Nov 10 - Nov 11

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

A fitness room with treadmills, an elliptical, and a stationary bike.

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

13. Tru by Hilton Chicopee Springfield

6.8 km from Winchester Square

Gary

₩146,361

₩166,047 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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

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

14. Fairfield Inn & Suites Springfield Holyoke

9.5 km from Winchester Square

Caroline

₩169,744

₩189,603 total

includes taxes & fees

Nov 1 - Nov 2

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

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

A hotel room with a striped sofa, a bed with a decorative headboard, a large wall painting, and a sunburst light fixture.

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

15. D. Hotel Suites & Spa

18.5 km from Winchester Square

Jim

₩162,358

₩189,978 total

includes taxes & fees

Oct 26 - Oct 27

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

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

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.

16. Naomi's Inn Bed & Breakfast

Liberty Heights, 3.6 km from Winchester Square

Peter

₩138,819

₩157,493 total

includes taxes & fees

Oct 14 - Oct 15

A hotel room with a sofa, a desk with a television, a chair, and a bed.

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

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

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

17. Homewood Suites by Hilton Holyoke-Springfield/North

9.1 km from Winchester Square

Andrew

₩196,723

₩219,740 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

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

18. Candlewood Suites West Springfield by IHG

5.2 km from Winchester Square

Richard

₩138,819

₩158,877 total

includes taxes & fees

Oct 18 - Oct 19

A stainless steel refrigerator with a digital display showing the time and date, a microwave above it, and a kettle on the stove.

A modern dining area with a glass table, black chairs, and a teal upholstered chair.

A living room with white sofas, a black and white rug, a staircase, and a coffee table with decorative items.

A bedroom with a bed, nightstands, and a wooden floor.

19. Upscaled Home in a Quiet Neighborhood

Forest Park, 3.8 km from Winchester Square

Anonymous traveler

₩420,462

₩650,538 total

includes taxes & fees

Oct 18 - Oct 19

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 large bed, bedside lamps, a desk, and a TV.

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

20. Residence Inn by Marriott West Springfield

6.1 km from Winchester Square

Joseph

₩178,863

₩204,708 total

includes taxes & fees

Oct 19 - Oct 20

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Compare popular hotels close to Winchester Square

Property	Property class	Guest rating
MGM Springfield	9.0 Wonderful 1,547 reviews	View
Hampton Inn & Suites Springfield/Downtown	8.6 Excellent 1,000 reviews	View
Hilton Garden Inn-Springfield, MA	8.6 Excellent 1,003 reviews	View
La Quinta Inn & Suites by Wyndham Springfield MA	8.0 Very good 1,255 reviews	View
Sheraton Springfield Monarch Place Hotel	8.0 Very good 1,004 reviews	View

Top Winchester Square Hotel Reviews

Marriott Springfield Downtown

10/10 Excellent

"Clean, helpful staff."

Hilton Garden Inn-Springfield, MA

10/10 Excellent

"Easy check in. Clean, spacious"

Sheraton Springfield Monarch Place Hotel

10/10 Excellent

"Wonderful stay"

Comfort Inn & Suites West Springfield

8/10 Good

"Hot Tub was warm FYI"

Riverdale Inn

8/10 Good

"To be honest, I wasn't expecting much. But to my surprise, everything was just fine. The room was clean, the bed was comfortable and the shower had hot water. I would stay again"

Howard Johnson by Wyndham Springfield

10/10 Excellent

"For the money, it was a nice stay. Comfortable beds and clean spacious room. For $150 I can't complain considering many nicer hotels in Spfld. are double the price. I would recommend it."

MGM Springfield

10/10 Excellent

"As usual, our stay at the MGM was excellent! We have been here many times and it seems to get better each time."

Hampton Inn & Suites Springfield/Downtown

10/10 Excellent

"Great location very quiet"

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.

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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 ₩157,493

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Treat yourself

Be picky

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Our top choices for Winchester Square hotels

1. MGM Springfield

2. Hampton Inn & Suites Springfield/Downtown

3. Hilton Garden Inn-Springfield, MA

4. La Quinta Inn & Suites by Wyndham Springfield MA

5. Sheraton Springfield Monarch Place Hotel

6. Marriott Springfield Downtown

7. Daniel Stebbins House

8. Residence Inn Springfield Chicopee

9. Blue A Modern Hotel, an Ascend Collection Hotel

10. Courtyard by Marriott West Springfield

11. Hampton Inn Springfield South Enfield

12. Holiday Inn Express Ludlow by IHG

13. Tru by Hilton Chicopee Springfield

14. Fairfield Inn & Suites Springfield Holyoke

15. D. Hotel Suites & Spa

16. Naomi's Inn Bed & Breakfast

17. Homewood Suites by Hilton Holyoke-Springfield/North

18. Candlewood Suites West Springfield by IHG

19. Upscaled Home in a Quiet Neighborhood

20. Residence Inn by Marriott West Springfield

Compare popular hotels close to Winchester Square

Top Winchester Square Hotel Reviews

Marriott Springfield Downtown

Hilton Garden Inn-Springfield, MA

Sheraton Springfield Monarch Place Hotel

Comfort Inn & Suites West Springfield

Riverdale Inn

Howard Johnson by Wyndham Springfield

MGM Springfield

Hampton Inn & Suites Springfield/Downtown

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