A white neoclassical building with columns, an American flag, and a clock tower.

2 Star Hotels in Winchester

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2 Star Hotels in Winchester

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Winchester on Hotels.com. These Winchester 2 Star Hotels consistently deliver on quality, location and traveler experience. Last updated on October 23, 2026.

A modern lobby with a seating area, a flat-screen TV, and a large window offering a view of the outdoors.

A hotel room with two beds, a desk, a chair, a desk lamp, a window with curtains, a bathroom with a mirror and sink.

A hotel reception area with a wooden reception desk, two computers, a map of the USA on the wall, and a small plant on the desk.

A modern lounge area with seating, a TV, and a children's play area.

1. Microtel Inn & Suites by Wyndham Winchester

Winchester

CNY561

CNY624 total

includes taxes & fees

Nov 8 - Nov 9

A modern hotel with a covered outdoor area, landscaped gardens, and a parking lot.

A hotel lobby with a blue sofa, red chairs, a patterned rug, and artwork on the walls.

A hotel room with two beds, a mounted painting, a nightstand with a phone, and a window with curtains.

A swimming pool with a metal railing, surrounded by lounge chairs and an umbrella.

2. Quality Inn Winchester

Winchester

CNY526

CNY586 total

includes taxes & fees

Nov 15 - Nov 16

A hotel dining area with multiple tables and chairs, large windows, and a television screen.

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

A hotel room with two beds, a desk with a TV, a lamp, and a view of the outdoors.

3. Comfort Inn & Suites Winchester

Winchester

CNY668

CNY743 total

includes taxes & fees

Nov 15 - Nov 16

A spacious restaurant with a central island, seating areas, and a mural on the back wall.

A fitness center with a water dispenser, seating area, and exercise machines.

A modern lounge area with seating arrangements, including sofas and chairs, and a large window providing a view outside.

An indoor swimming pool with clear lane markings, a lifeguard chair, and a safety ring on the wall.

4. TRU By Hilton Winchester

Winchester

CNY569

CNY634 total

includes taxes & fees

Nov 1 - Nov 2

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

A spacious lobby with a seating area featuring yellow patterned chairs, a flat-screen TV mounted on the wall, and a large window providing natural light.

A conference room with a projector screen, arranged chairs, and a carpeted floor.

A large conference room with multiple tables and chairs, carpeted floor, and ceiling lights.

5. Hampton Inn Winchester N/Conference Center, VA

Winchester

CNY640

CNY726 total

includes taxes & fees

Nov 9 - Nov 10

A modern living room with a sofa, armchair, dining table, and chairs. There is a TV mounted on the wall and a small table with a lamp.

A hotel room with two beds, a wooden headboard, a nightstand with lamps, and a view of the outdoors through the window.

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

A spacious indoor area with a long table and chairs, a statue, and a large window.

6. Travelodge by Wyndham Winchester

Winchester

CNY474

CNY523 total

includes taxes & fees

Nov 1 - Nov 2

An outdoor patio with a fire feature, seating, and a covered area.

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

An indoor swimming pool with clear water, metal railings, and lounge chairs.

A modern hotel with a covered entrance, a sign reading "SPRINGHILL SUITES BY MARRIOTT," and a landscaped area with plants.

7. SpringHill Suites by Marriott Winchester

Winchester

CNY758

CNY843 total

includes taxes & fees

Nov 8 - Nov 9

A hotel room with a bed, a brown sofa, a round table, a lamp, a window with a decorative screen, and a framed picture on the wall.

A kitchenette with a coffee machine, a fruit basket, and a mini-fridge.

A reception area with a wooden desk, a black rug, and a patterned wall.

A modern hotel room with a large desk, a comfortable sofa, a flat-screen TV, and a large window with a view.

8. Candlewood Suites Winchester by IHG

Winchester

CNY534

CNY594 total

includes taxes & fees

Nov 1 - Nov 2

A lobby with a green wall, a reception desk, and seating area with sofas and armchairs.

A living room with a brown sofa, two armchairs, a coffee table, and two lamps. There are two windows with blinds, and a wall with a leaf pattern.

A Sleep Inn hotel with a stone facade, multiple balconies, and a parking lot with several cars.

A modern hotel lobby with a reception desk, a coffee station, and a seating area.

9. Sleep Inn & Suites Winchester near University

Winchester

CNY511

CNY568 total

includes taxes & fees

Nov 15 - Nov 16

A modern dining area with a large white table, blue chairs, and a flat-screen TV mounted on the wall.

An indoor swimming pool with a lifeguard chair, a pool lift, and a window.

A Holiday Inn Express & Suites building with a covered entrance, large windows, and a fire lane.

A hotel room with a bed, a desk, a chair, a window with a view, and a TV on the wall.

10. Holiday Inn Express Hotel & Suites Winchester by IHG

Winchester

CNY734

CNY817 total

includes taxes & fees

Nov 22 - Nov 23

A hotel room with two beds, a blue armchair, a nightstand with a lamp, and a wall-mounted painting.

A hotel with a registration sign, a parking lot, and a tree in front.

A seating area with two chairs and a lamp, a sign indicating continental breakfast hours, and a door with a small window.

A seating area with two blue leather chairs and a beverage vending machine.

11. Days Inn by Wyndham Winchester

Winchester

CNY421

CNY468 total

includes taxes & fees

Oct 26 - Oct 27

A modern interior with a reception desk, seating area, and large windows offering a view of the street.

A vending machine with snacks and a water dispenser.

A reception area with a white reception desk, a grey carpet, and a view of the street outside.

A hotel room with two beds, a desk with a chair, a microwave, a TV, and a bathroom visible through an open door.

12. Motel 6 Winchester, VA

Winchester

CNY454

CNY514 total

includes taxes & fees

Nov 5 - Nov 6

A restaurant with wooden tables and red cushioned chairs, a kitchen area with a coffee machine, and a large window.

A gym with an elliptical, dumbbells, a treadmill, and a wall-mounted phone.

A reception area with a marble counter, a desk, and a framed picture on the wall.

A two-story building with a brick facade and a beige exterior.

13. Quality Inn Stephens City - Winchester South

Stephens City

CNY548

CNY610 total

includes taxes & fees

Nov 15 - Nov 16

A hotel lobby with a reception desk, a check-in counter, a seating area with chairs, and a dining area in the background.

A hotel with a green roof, a covered entrance, and a sign that reads "RAMADA".

A hotel lobby with a polished tile floor, a reception desk, and seating area with white chairs.

A modern hotel lobby with a clear exit sign, a reception desk, and a seating area with red chairs.

14. Ramada by Wyndham Strasburg/Shenandoah Valley

Strasburg

CNY505

CNY562 total

includes taxes & fees

Nov 2 - Nov 3

A gym with exercise equipment, including a bench, red exercise balls, and a variety of weights.

A swimming pool with a blue cover, a no diving sign, and a no lifeguard sign.

A hotel room with a desk, a television, a framed picture on the wall, and a chair.

A Hampton Inn hotel with a clear blue sky, a parking lot, and well-maintained landscaping.

15. Hampton Inn Winchester-University/Mall Area

Winchester

CNY636

CNY720 total

includes taxes & fees

Nov 1 - Nov 2

A hotel room with two beds, a nightstand, a lamp, and two framed waterfall paintings on the wall.

A room with a green sofa, a wooden table, a flat-screen TV, a window with blinds, and a tiled floor.

A vending area with snack and drink machines, a refrigerator, and a Coca-Cola machine.

A hotel lobby with a vending machine, a reception desk, and a wall sign reading "Super 8".

16. Super 8 by Wyndham Winchester VA

Winchester

CNY391

CNY435 total

includes taxes & fees

Nov 5 - Nov 6

A hotel room with a bed, bedside table, lamp, chair, and a desk with a chair.

A kitchen with a refrigerator, a coffee machine, and a microwave.

A hotel reception area with a modern design, including a reception desk, a stone accent wall, and a sign indicating free Wi-Fi availability.

A modern kitchen with a built-in coffee machine, a microwave, and a refrigerator.

17. Red Roof Inn Winchester, VA

Winchester

CNY467

CNY520 total

includes taxes & fees

Nov 2 - Nov 3

A room with a dining table and chairs, a bed, and a kitchen area visible through an open doorway.

A brick building with a sign reading "Boston - Bryant Theatre."

A hotel room with a large bed, two armchairs, a small table with a lamp, a round mirror, and a window with curtains.

A wooden table with a wine bottle and two glasses on it, set outdoors with a view of greenery in the background.

18. ANS Inn & Suites

Winchester

CNY481

CNY573 total

includes taxes & fees

Nov 5 - Nov 6

A covered outdoor area with a table and chairs, a brick wall, and a metal railing.

A sign for a 'Relax Inn' with a clear view of the building in the background.

A brick building with a sign reading "Motel" and a neon sign for "Relax Inn" on the right.

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

19. Relax Inn Motel

Front Royal

CNY434

CNY483 total

includes taxes & fees

Oct 25 - Oct 26

A modern hotel lobby with a green sofa, blue chairs, a dining table, and large windows offering a view of the outdoors.

A rectangular swimming pool with a brick wall and trees in the background.

A modern breakfast area with seating, a counter for hot food, and a view of the outdoors.

A hotel reception desk with a blue accent, a Holiday Inn Express sign, and a coffee station.

20. Holiday Inn Express Winchester South-Stephens City by IHG

Stephens City

CNY587

CNY654 total

includes taxes & fees

Nov 1 - Nov 2

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Top neighborhoods in Winchester

A red brick church with a blue door and a clock tower.

A brick building with a cafe on the ground floor and a church steeple in the background.

A brick-paved street lined with shops and cafes, under a cloudy sky.

A building with a green roof and ornate architectural details.

Old Town Winchester

Winchester's Old Town Winchester neighborhood is known for its restaurants and bars, and entices visitors with attractions including Bright Box Theater and Shenandoah Valley Discovery Museum.

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A stone building with a sign reading "W. 8th Street."

A building with a sign that reads "Snow White Grill" and "Winchester's Original Burger Joint."

Winchester Historic District

Winchester's Winchester Historic District neighborhood is home to attractions such as Bright Box Theater and Shenandoah Valley Discovery Museum.

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Top landmarks in Winchester

A brick pathway leading to a central lawn area, surrounded by trimmed hedges and trees.

Museum of the Shenandoah Valley

8.8/10 (129 reviews)

Museum of the Shenandoah Valley is 0.8 mi (1.3 km) from central Winchester, why not stop by during your stay. If you want to experience more of the culture Winchester has to offer, head to Shenandoah Valley Discovery Museum, Bright Box Theater, and ValleyHealth Winchester Medical Center.

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A tall tree with a textured trunk and dense green foliage.

Jim Barnett Park

8.6/10 (88 reviews)

Jim Barnett Park is 0.9 mi (1.5 km) from central Winchester, why not stop by during your stay. Our travelers also like this walkable area for its restaurants. Want to stretch your legs some more? Head to Star Fort Civil War Battlefield, located nearby.

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Shenandoah University

8.8/10 (276 reviews)

If you'd like to get a taste of Winchester student life, check out Shenandoah University, located 1.2 mi (2 km) from central Winchester.

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Apple Blossom Mall

8.2/10 (315 reviews)

If you like shopping, take time out to go to Apple Blossom Mall when in Winchester.

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Patsy Cline Historic House

8.4/10 (104 reviews)

You might want to get your camera out and head to Patsy Cline Historic House— just one of the landmarks located 0.4 mi (0.7 km) from central Winchester.

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Shenandoah Valley Discovery Museum

8.6/10 (78 reviews)

Old Town Winchester is home to Shenandoah Valley Discovery Museum, so why not stop by during your stay in Winchester.

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Rock Harbor Golf Course

7.6/10 (49 reviews)

You might want to play some rounds at Rock Harbor Golf Course, located 2.2 mi (3.5 km) from central Winchester.

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Bright Box Theater

7.8/10 (18 reviews)

If you want to see a show while you're in town, try and grab some tickets at Bright Box Theater in Old Town Winchester. If you enjoy the show and want to see another, Winchester Little Theater is just a short walk away.

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