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

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

1. MGM Springfield

Metro Center, 2.3 km from Winchester Square

Carla

NT$4,792

NT$6,166 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

2. Hampton Inn & Suites Springfield/Downtown

South End, 2.4 km from Winchester Square

James

NT$3,800

NT$4,311 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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.

3. Hilton Garden Inn-Springfield, MA

South End, 2.6 km from Winchester Square

Richard

NT$4,073

NT$4,621 total

includes taxes & fees

Nov 3 - Nov 4

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.

4. La Quinta Inn & Suites by Wyndham Springfield MA

Metro Center, 2.5 km from Winchester Square

Heather

NT$3,554

NT$4,032 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 multi-level hotel lobby with a central staircase, decorative murals, and a chandelier.

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

5. Sheraton Springfield Monarch Place Hotel

Metro Center, 2.5 km from Winchester Square

Brittany

NT$5,178

NT$5,890 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 lounge area with a central fire feature, comfortable seating, and a staircase in the background.

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

6. Marriott Springfield Downtown

Metro Center, 2.5 km from Winchester Square

Nataliya

NT$4,655

NT$5,281 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 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.

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

NT$8,692

NT$9,708 total

includes taxes & fees

Oct 25 - Oct 26

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.

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

8. Residence Inn Springfield Chicopee

6.9 km from Winchester Square

Ronald

NT$5,440

NT$6,172 total

includes taxes & fees

Oct 25 - Oct 26

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

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

9. Blue A Modern Hotel, an Ascend Collection Hotel

6 km from Winchester Square

Charles

NT$3,444

NT$3,942 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 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.

10. Courtyard by Marriott West Springfield

5.4 km from Winchester Square

Amy

NT$4,217

NT$4,827 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 gym with treadmills, elliptical machines, and a bench.

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

11. Hampton Inn Springfield South Enfield

13.7 km from Winchester Square

kelly

NT$4,375

NT$5,031 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 compact kitchen with wooden cabinets, a white refrigerator, a microwave, a coffee maker, and a sink. There are two bar stools at the island.

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

NT$3,410

NT$3,809 total

includes taxes & fees

Nov 15 - Nov 16

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

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

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

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

13. Tru by Hilton Chicopee Springfield

6.8 km from Winchester Square

Gary

NT$3,527

NT$4,001 total

includes taxes & fees

Nov 9 - Nov 10

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

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

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

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

14. D. Hotel Suites & Spa

18.5 km from Winchester Square

JOHN

NT$3,912

NT$4,577 total

includes taxes & fees

Oct 27 - Oct 28

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.

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

15. Fairfield Inn & Suites Springfield Holyoke

9.5 km from Winchester Square

Caroline

NT$4,074

NT$4,551 total

includes taxes & fees

Nov 1 - Nov 2

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 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

NT$3,377

NT$3,831 total

includes taxes & fees

Oct 18 - Oct 19

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

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

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

A modern kitchen with white cabinetry, a stainless steel dishwasher, a microwave, and a granite countertop.

17. Homewood Suites by Hilton Holyoke-Springfield/North

9.1 km from Winchester Square

Andrew

NT$5,276

NT$5,893 total

includes taxes & fees

Nov 1 - Nov 2

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.

18. Candlewood Suites West Springfield by IHG

5.2 km from Winchester Square

Richard

NT$3,345

NT$3,828 total

includes taxes & fees

Oct 18 - Oct 19

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

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

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.

19. Residence Inn by Marriott West Springfield

6.1 km from Winchester Square

Joseph

NT$4,311

NT$4,934 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

20. Upscaled Home in a Quiet Neighborhood

Forest Park, 3.8 km from Winchester Square

Anonymous traveler

NT$10,131

NT$15,674 total

includes taxes & fees

Nov 14 - Nov 15

View all properties

Compare popular hotels close to Winchester Square

Property	Property class	Guest rating
MGM Springfield	9.0 Wonderful 1,544 reviews	View
Hampton Inn & Suites Springfield/Downtown	8.6 Excellent 1,001 reviews	View
Hilton Garden Inn-Springfield, MA	8.6 Excellent 1,004 reviews	View
La Quinta Inn & Suites by Wyndham Springfield MA	8.0 Very good 1,251 reviews	View
Sheraton Springfield Monarch Place Hotel	8.0 Very good 1,001 reviews	View

Top Winchester Square Hotel Reviews

Howard Johnson by Wyndham Springfield

8/10 Good

"It was decent."

Red Roof Inn PLUS+ West Springfield

10/10 Excellent

"The hotel was close everything very nice Clean staff was accommodating"

Holiday Inn Express Springfield Downtown by IHG

10/10 Excellent

"Super service, surtout le préposé de soir, sympathique et à l’écoute des clients 😊"

Best Western Springfield West Inn

10/10 Excellent

"Hotel was very clean, staff helpful and good location."

Sheraton Springfield Monarch Place Hotel

10/10 Excellent

"Good check in; helpful staff"

Hampton Inn West Springfield

8/10 Good

"Room was clean, microwave and refrigerator clean and working, staff was friendly and helpful. Breakfast was better than most. The bath however had problems. The water faucet was loose and not connected to the tub and the water control was difficult to pull to start. Tub plug was very hard to use."

Quality Inn West Springfield

10/10 Excellent

"Overall I had a great two day stay at the Quality Inn. I have stayed here over a dozen times when in the area to visit Six Flags, my previous visit was in the spring, and they have made some updates since! I noticed new chairs in the hallways and room, and the exterior of the building was repainted a new color and looks more modern! I had room 421, a 2 queen, which was mostly clean and comfortable. Only issue was the new tan chair by the door looked comfortable, but I did not sit in it, as it had long hairs and sticky residue all over the cushion... Otherwise the room was clean, beds were comfortable with 4 pillows on each bed, lots of towels, and fridge worked great! The lamp between the bed did not work though... At check in, the man with tattoos on his hands wasn't that friendly or welcoming but did honor my request for a higher floor. Later, when returning from dinner next door (Great Japanese restaurant!) I heard him tell a guest she had the entire 5th floor to herself, which was annoying as each night I had neighbors who I could hear easily through the walls... Why not space out guests when there is space? I woke up my first morning to hearing the neighbors talk... Breakfast was fine with a decent variety, I liked the donuts, eggs were decent, as was the sausage. The room was a great value and I will return. It looks like the first floor was restored for guest use again too! Nice to see some changes and hope they continue renovating and updating the property!"

Courtyard by Marriott West Springfield

8/10 Good

"The room smelt a bit musty/BO s and the shower head was terrible. Good guest laundry facilities, bed was super comfy and room was generally clean. Wifi was moderate. Location handy for nearby suburbs and close to shops."

Hilton Garden Inn-Springfield, MA

10/10 Excellent

"I like the convenience of the location. Can get to places very quickly. And immediately back on the highway."

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 NT$3,809

Change your mind

Treat yourself

Be picky

Check prices for these dates

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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. D. Hotel Suites & Spa

15. Fairfield Inn & Suites Springfield Holyoke

16. Naomi's Inn Bed & Breakfast

17. Homewood Suites by Hilton Holyoke-Springfield/North

18. Candlewood Suites West Springfield by IHG

19. Residence Inn by Marriott West Springfield

20. Upscaled Home in a Quiet Neighborhood

Compare popular hotels close to Winchester Square

Top Winchester Square Hotel Reviews

Howard Johnson by Wyndham Springfield

Red Roof Inn PLUS+ West Springfield

Holiday Inn Express Springfield Downtown by IHG

Best Western Springfield West Inn

Sheraton Springfield Monarch Place Hotel

Hampton Inn West Springfield

Quality Inn West Springfield

Courtyard by Marriott West Springfield

Hilton Garden Inn-Springfield, MA

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