The Best Hotels Closest to Winchester Square in Springfield - 2026 Updated Prices

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Our top choices for Winchester Square hotels

A corner building with a large entrance, a sign for 'Hilton Express', and a street sign for 'Willow St'.

An indoor swimming pool with a tiled edge, a reception area with a counter and chairs, and a door to the right.

A modern restaurant with blue and red seating, a counter area, and framed pictures on the walls.

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

1. Holiday Inn Express Springfield Downtown by IHG

Metro Center, 1.3 mi from Winchester Square

Mykola

£97

includes taxes & fees

16 Sept - 17 Sept

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

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

2. MGM Springfield

Metro Center, 1.4 mi from Winchester Square

Heather

£137

includes taxes & fees

1 Sept - 2 Sept

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

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.

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

3. Hilton Garden Inn-Springfield, MA

South End, 1.6 mi from Winchester Square

Janette

£102

includes taxes & fees

1 Sept - 2 Sept

A hotel dining area with a long table, chairs, a sofa, and a large pendant light.

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 a desk, TV, red sofa, and large windows with curtains.

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

4. Hampton Inn & Suites Springfield/Downtown

South End, 1.5 mi from Winchester Square

Janet

£88

includes taxes & fees

30 Aug - 31 Aug

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.

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

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, 1.6 mi from Winchester Square

luc

£99

includes taxes & fees

7 Sept - 8 Sept

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

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

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.

6. Marriott Springfield Downtown

Metro Center, 1.5 mi from Winchester Square

Demetria

£129

includes taxes & fees

6 Sept - 7 Sept

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

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

7. Sheraton Springfield Monarch Place Hotel

Metro Center, 1.5 mi from Winchester Square

Silvino

£135

includes taxes & fees

31 Aug - 1 Sept

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

8. Blue A Modern Hotel, an Ascend Collection Hotel

3.7 mi from Winchester Square

Cynthia

£93

includes taxes & fees

8 Sept - 9 Sept

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

9. Courtyard by Marriott West Springfield

3.3 mi from Winchester Square

Shannon

£103

includes taxes & fees

7 Sept - 8 Sept

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.

10. Fairfield Inn & Suites Springfield Holyoke

5.9 mi from Winchester Square

Michael

£101

includes taxes & fees

13 Sept - 14 Sept

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

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

11. Hampton Inn Springfield South Enfield

8.5 mi from Winchester Square

Jennifer

£115

includes taxes & fees

28 Aug - 29 Aug

A buffet with labeled containers of omelets and other dishes.

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

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

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

12. Holiday Inn Express Ludlow by IHG

5.7 mi from Winchester Square

Erin

£101

includes taxes & fees

30 Aug - 31 Aug

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.

13. Naomi's Inn Bed & Breakfast

Liberty Heights, 2.2 mi from Winchester Square

Susan

£85

includes taxes & fees

20 Aug - 21 Aug

A modern lounge area with seating options including sofas, chairs, and a hanging chair. Tables and a counter are also visible.

A modern hotel room with a bed, desk, and chair, a small kitchenette, and a bathroom with a shower and toilet.

A modern hotel entrance with a glass door, a visible address number, and a clear pathway leading to the entrance.

A food kiosk with a variety of snacks and beverages, a sign for local items, and a counter with a beverage display.

14. Tru by Hilton Chicopee Springfield

4.2 mi from Winchester Square

Leon

£95

includes taxes & fees

25 Aug - 26 Aug

15. Homewood Suites by Hilton Holyoke-Springfield/North

5.7 mi from Winchester Square

Lauren

£101

includes taxes & fees

30 Aug - 31 Aug

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

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.

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

16. Residence Inn by Marriott West Springfield

3.8 mi from Winchester Square

Deborah

£106

includes taxes & fees

23 Aug - 24 Aug

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

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

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

An indoor swimming pool with a hot tub, lounge chairs, and a tiled floor.

17. Candlewood Suites West Springfield by IHG

3.3 mi from Winchester Square

Malcolm

£76

includes taxes & fees

30 Aug - 31 Aug

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

A window with a view of a parking lot and a building with outdoor furniture.

A hotel room with a bed, a bathtub, a sink, a mirror, a plant, and a framed picture on the wall.

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

5.2 mi from Winchester Square

Chris

£105

includes taxes & fees

20 Aug - 21 Aug

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

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

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

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

19. Hampton Inn Westfield

8.8 mi from Winchester Square

Ace

£94

includes taxes & fees

8 Sept - 9 Sept

A modern living room with a fireplace, comfortable seating, and a large window with sheer curtains.

A modern hotel reception area with a wooden reception desk, a large abstract artwork, and a view of the sky through a large window.

A gazebo in a grassy area with wooden barrels and benches, surrounded by trees and a white fence.

20. Fairfield Inn & Suites by Marriott Springfield Enfield

6.3 mi from Winchester Square

Georges

£123

includes taxes & fees

30 Aug - 31 Aug

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Compare popular hotels close to Winchester Square

Property	Property class	Guest rating
Holiday Inn Express Springfield Downtown by IHG	9.0 Wonderful 1,259 reviews	View
MGM Springfield	9.0 Wonderful 1,548 reviews	View
Hilton Garden Inn-Springfield, MA	8.6 Excellent 1,011 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 1,292 reviews	View

Top Winchester Square Hotel Reviews

Tru by Hilton Chicopee Springfield

10/10 Excellent

"Great place to stay!! Clean, we'll taken care of!!"

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent

"we were there for SIX FLAGS NEW ENGLAND ... used the pool once ... could use a good cleaning "

Holiday Inn Express Springfield Downtown by IHG

10/10 Excellent

"My husband and I had a comfortable stay. Would definitely book again"

Hampton Inn West Springfield

10/10 Excellent

"Staff was great, room was roomy, clean and well appointed."

Candlewood Suites West Springfield by IHG

8/10 Good

"It’s been 5 days since I checked out and I still have not gotten back my $100 security deposit. Reached out twice and was told both times they don’t know why, and to call back again to try and get ahold of the property manager. The hotel was very nice though. Besides what I said above (and assuming I do get that back) I would definitely stay again."

Baldwin Inn & Suites, SureStay Collection by Best Western

8/10 Good

"It was exactly as you paid for. Nice, clean and friendly just a little bit old."

Quality Inn West Springfield

10/10 Excellent

"Priced right & the staff was amazingly friendly and helpful. Basic accommodations & sweet ppl: highly recommend."

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? Visit 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, take a look at the 17 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 17 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. Storrowton Village Museum, Josiah Day House and Springfield City Library are monuments to see when you're exploring the area around Winchester Square. You can watch performances at Majestic Theatre, Appleton Auditorium and CityStage Symphony Hall if you're interested in local theatre.

Search Hotels Near Winchester Square, Springfield

Change your mind

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. Marriott Springfield Downtown

7. Sheraton Springfield Monarch Place Hotel

8. Blue A Modern Hotel, an Ascend Collection Hotel

9. Courtyard by Marriott West Springfield

10. Fairfield Inn & Suites Springfield Holyoke

11. Hampton Inn Springfield South Enfield

12. Holiday Inn Express Ludlow by IHG

13. Naomi's Inn Bed & Breakfast

14. Tru by Hilton Chicopee Springfield

15. Homewood Suites by Hilton Holyoke-Springfield/North

16. Residence Inn by Marriott West Springfield

17. Candlewood Suites West Springfield by IHG

18. Wilbraham Inn

19. Hampton Inn Westfield

20. Fairfield Inn & Suites by Marriott Springfield Enfield

Compare popular hotels close to Winchester Square

Top Winchester Square Hotel Reviews

Tru by Hilton Chicopee Springfield

La Quinta Inn & Suites by Wyndham Springfield MA

Holiday Inn Express Springfield Downtown by IHG

Hampton Inn West Springfield

Candlewood Suites West Springfield by IHG

Baldwin Inn & Suites, SureStay Collection by Best Western

Quality Inn West Springfield

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