Winchester Holiday Rentals, Virginia: Private House Rentals

A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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Our top choices for Winchester hotels

A modern dining area with a high ceiling, recessed lighting, and a large window providing natural light.

A gym with treadmills, elliptical machines, and dumbbells.

A modern lounge area with a sofa, chairs, and tables, featuring a patterned carpet and a decorative ceiling light.

A modern hotel with a flat facade, multiple windows, and a well-lit entrance.

1. La Quinta Inn & Suites by Wyndham Winchester

Winchester

Raquel

2.699.963 ₫

3.005.058 ₫ total

includes taxes & fees

6 Sept - 7 Sept

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

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.

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

2. Microtel Inn & Suites by Wyndham Winchester

Winchester

Ricky

2.252.794 ₫

2.507.360 ₫ total

includes taxes & fees

6 Sept - 7 Sept

A spacious lobby with a checkered floor, yellow chairs, a green carpet, and a wall with the text "It only takes a spark".

An indoor swimming pool with clear glass walls, a tiled floor, and a few lounge chairs.

A modern hotel room with a bed, sofa, and a small table. There are two doors, one blue and one white, and a small table with chairs.

A hotel with a modern design, featuring a prominent 'spark by Hilton' sign, a well-lit entrance, and a landscaped front yard.

3. Spark by Hilton Winchester

Winchester

Alexandra

2.011.925 ₫

2.279.510 ₫ total

includes taxes & fees

28 Sept - 29 Sept

An indoor swimming pool with clear blue water, surrounded by large windows offering views of greenery.

A gym with weightlifting equipment, including dumbbells and a bench.

A hotel room with a gray sofa, a bed with a blue headboard, a painting of a landscape, and a lamp on the nightstand.

4. Hampton Inn Front Royal

Front Royal

Timothy

3.188.287 ₫

3.548.562 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A self-service beverage station with a refrigerated drink dispenser, a coffee machine, and a variety of snacks.

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

5. TRU By Hilton Winchester

Winchester

Gerley

2.330.494 ₫

2.593.839 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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 reception area with a stone counter, a chandelier, a desk with a computer, and a seating area with chairs and a table.

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

6. Travelodge by Wyndham Winchester

Winchester

Thomas

1.983.220 ₫

2.187.544 ₫ total

includes taxes & fees

5 Sept - 6 Sept

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 hotel reception area with a black counter, coffee dispensers, a juice dispenser, and a small refrigerator.

7. Quality Inn Winchester

Winchester

Scott

2.083.313 ₫

2.318.727 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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

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

8. Comfort Inn & Suites Winchester

Winchester

Sandra

2.421.616 ₫

2.695.259 ₫ total

includes taxes & fees

4 Oct - 5 Oct

A Holiday Inn hotel with a modern design, featuring a covered entrance and multiple floors.

A spacious lobby with a checkered floor, a reception desk, and a seating area with a sofa and chairs.

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

A bar area with a counter, multiple bar stools, and a television screen.

9. Holiday Inn Winchester Se-Historic Gateway by IHG

Winchester

Jennifer

2.687.785 ₫

3.069.790 ₫ total

includes taxes & fees

4 Oct - 5 Oct

A modern hotel lobby with a sofa set, two armchairs, a coffee table, and a reception desk.

A Fairfield by Marriott hotel with a modern entrance, stone pillars, and a well-lit facade.

A modern restaurant interior with wooden tables and chairs, a green booth area, and artwork on the walls.

A coffee station with multiple coffee dispensers and a sign above.

10. Fairfield Inn & Suites by Marriott Winchester

Winchester

Michael

2.415.756 ₫

2.688.737 ₫ total

includes taxes & fees

8 Sept - 9 Sept

A courtyard with a fountain, tables with white tablecloths, and brick buildings.

A large brick building with a classic facade, a central entrance with a decorative arch, and a sign reading "The George Washington Hotel."

A spacious lobby with a round table, chairs, a chandelier, and an American flag.

A bar area with a piano, seating, and a bar counter with bottles.

11. The George Washington Hotel, A Wyndham Grand Hotel

Old Town Winchester

Jeanette

3.399.528 ₫

3.851.665 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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 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.

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

12. Ramada by Wyndham Strasburg/Shenandoah Valley

Strasburg

Maryann

2.016.824 ₫

2.244.727 ₫ total

includes taxes & fees

10 Sept - 11 Sept

A restaurant interior with a bar area, seating, and artwork on the walls.

A hotel lobby with a reception desk, a minibar, a seating area, and a clothing rack.

An indoor swimming pool with a hot tub, lounge chairs, and a view of the outdoors.

A spacious lobby with a reception desk, seating area with sofas, and a chandelier.

13. DoubleTree by Hilton Front Royal Blue Ridge Shadows

Front Royal

Alok

3.185.721 ₫

3.513.850 ₫ total

includes taxes & fees

24 Sept - 25 Sept

A modern hotel lobby with a reception desk, seating area, and a large window providing natural light.

A hotel lobby with a reception desk, refrigerated display cases, shelves with snacks, and a trash bin.

A modern kitchen with wooden cabinets, a countertop, and a window with a view.

A lobby with yellow patterned chairs, a round table, a TV on the wall, and a patterned rug.

14. Hampton Inn Winchester N/Conference Center, VA

Winchester

Jackie

2.758.108 ₫

3.124.936 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A spacious lobby with a stone fireplace, red chairs, a wooden staircase, and a flat-screen TV mounted on the wall.

A stainless steel kitchen with a built-in water dispenser and a window with blinds.

A hotel lobby with a wooden railing, a reception desk, a flower vase, and an exit sign.

A hotel room with a large bed, a ceiling fan, a nightstand, a window with curtains, and a view of the ocean.

15. Motel 6 Front Royal, VA

Front Royal

Robert

1.695.914 ₫

1.887.553 ₫ total

includes taxes & fees

1 Oct - 2 Oct

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

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

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

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

16. SpringHill Suites by Marriott Winchester

Winchester

Michael

2.959.920 ₫

3.294.391 ₫ total

includes taxes & fees

10 Sept - 11 Sept

A Courtyard by Marriott hotel with a covered entrance, multiple floors, and a brick facade.

An outdoor seating area with wicker furniture and a small table, surrounded by greenery and a building in the background.

A modern hotel lobby with a curved sofa, a glass coffee table, and a flat-screen TV mounted on the wall.

A bar area with a display case of baked goods, a fruit basket, and a television screen displaying news.

17. Courtyard by Marriott Winchester

Winchester

David

2.792.525 ₫

3.108.080 ₫ total

includes taxes & fees

10 Sept - 11 Sept

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 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.

A multi-story hotel with a prominent entrance, a parking lot, and surrounding greenery.

18. Candlewood Suites Winchester by IHG

Winchester

Bridget

2.190.216 ₫

2.437.658 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A swimming pool area with a fence, lounge chairs, and a flag.

A reception desk with a green wall, a plant, and various informational posters.

A hotel room with two beds, a nightstand with lamps, a vase with flowers, and framed leaf artwork on the walls.

A building entrance with a neon 'OPEN' sign, a reception desk, and a clock.

19. Twi-Lite Inn

Front Royal

Jacob

2.138.068 ₫

2.379.774 ₫ total

includes taxes & fees

10 Sept - 11 Sept

A hotel lobby with a reception desk, seating area with a round table, and a bar.

A hotel reception desk with a computer, two chairs, and a large mirror.

A multi-story hotel with a prominent sign for Marriott.

A modern hotel dining area with a long table, multiple chairs, and a large window providing natural light.

20. Fairfield Inn & Suites Strasburg Shenandoah Valley

Strasburg

Patrick

3.195.369 ₫

3.556.445 ₫ total

includes taxes & fees

23 Sept - 24 Sept

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Where to stay in Winchester

Find the best Winchester areas for the activities you enjoy most.

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

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 church with a tall steeple and a clock, illuminated by street lamps.

Old Town Winchester

Old Town Winchester is popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to Bright Box Theater or Shenandoah Valley Discovery Museum.

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

A building with a green roof and ornate architectural details.

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.

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Stay near popular Winchester attractions

Museum of the Shenandoah Valley

8.8/10 (129 reviews)

Discover the Shenandoah Valley's rich heritage at this cultural cornerstone. Wander through the historic Glen Burnie House and meticulously designed gardens for a refined afternoon of regional exploration.

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Shenandoah University

8.8/10 (276 reviews)

This prestigious Virginia university shines with its acclaimed Conservatory for performing arts and vibrant campus life. Catch a student concert or theatrical production for an enriching cultural experience.

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Apple Blossom Mall

8.2/10 (315 reviews)

Apple Blossom Mall offers over 60 stores and an AMC 12-screen theatre in Winchester's premier shopping destination. Browse fashion retailers, speciality shops, and diverse dining options in this comprehensive retail hub.

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Patsy Cline Historic House

8.4/10 (104 reviews)

Step back in time at the modest four-room house where country music legend Patsy Cline spent her childhood. Tours showcase original furnishings and artefacts, offering glimpses into her journey to stardom.

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Shenandoah Valley Discovery Museum

8.6/10 (78 reviews)

This four-floor interactive museum sparks curiosity through hands-on exhibits for young explorers. Families can experiment together in the morning hours, before the midday crowds arrive.

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Rock Harbor Golf Course

7.6/10 (49 reviews)

Carved from quarry landscapes, Rock Harbour offers two championship golf courses with dramatic elevation changes and water hazards. Navigate the challenging Boulder Course or enjoy the more forgiving Rock Course amid valley vistas.

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Bright Box Theater

7.8/10 (18 reviews)

This vibrant venue in Old Town Winchester hosts over 200 live music, comedy, and drag performances annually. Arrive early to secure prime seating and enjoy craft beers and bistro fare before the show begins.

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Stonewall Jackson's Headquarters

10.0/10 (1 review)

Step back in time at this Gothic Revival house where Confederate General "Stonewall" Jackson strategized during winter 1861-1862. Explore his artefacts while guides reveal the general's military genius.

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Winchester and related destinations

Stroll through the charming pedestrian mall in the historic district, where shops and excellent restaurants await. Delve into local culture at the Museum of the Shenandoah Valley or catch a show at the Bright Box Theatre.

See all hotels in Winchester

Top Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"Room was large and in very good condition. Plenty of parking. Might be a bit noisy on the side that faces the highway"

Quality Inn Winchester

10/10 Excellent

"Convenient and surprisingly nice for the price"

SpringHill Suites by Marriott Winchester

10/10 Excellent

"From the early very friendly check-in to the delicious breakfast before leaving. we had a wonderful stay"

Travelodge by Wyndham Winchester

10/10 Excellent

"Clean room, convenient, bed was co.fortablr. great low price option."

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent

"Our stay here was wonderful! Very friendly and helpful staff. The cleanliness was excellent ! We will definitely stay here again."

Courtyard by Marriott Winchester

10/10 Excellent

"Excellent"

Candlewood Suites Winchester by IHG

10/10 Excellent

"nothing more to add."

Days Inn by Wyndham Winchester

8/10 Good

"Not too shabby. I would stay again"

Lansdowne Resort and Spa

8/10 Good

"Very clean property. Nice rooms, but the beds were pretty firm, seemed like the pillow top had bed squished over time, likely needs to be replaced. We asked for extra padding for the bed and were thankfully able to get some which helped. The pools are nice but close early. The ping pong table and corn hole can't be used after the pool closes, not a very good set up with that, but there are 2 pool tables in one of the restaurants. Overall we would stay again as long as we could get extra padding for the bed again."

More cheap stays in Winchester

Quality Inn Luray

410 W Main St Luray VA

1.662.218 ₫

1.916.537 ₫ total

24 Sept - 25 Sept

includes taxes & fees

7.6/10 Good! (1,006 reviews)

Ramada by Wyndham Strasburg/Shenandoah Valley

21 Signal Knob Dr Strasburg VA

2.016.824 ₫

2.244.727 ₫ total

10 Sept - 11 Sept

includes taxes & fees

8.2/10 Very good! (1,002 reviews)

Quality Inn Winchester

1601 Martinsburg Pike Winchester VA

2.083.313 ₫

2.318.727 ₫ total

13 Sept - 14 Sept

includes taxes & fees

9.4/10 Exceptional! (1,002 reviews)

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza Winchester VA

2.252.794 ₫

2.507.360 ₫ total

6 Sept - 7 Sept

includes taxes & fees

Comfort Inn & Suites Winchester

195 Kernstown Commons Blvd Winchester VA

2.421.616 ₫

2.695.259 ₫ total

4 Oct - 5 Oct

includes taxes & fees

Skyland

Skyline Dr Mile 41.7 & 42.5 Luray VA

4.604.493 ₫

5.308.994 ₫ total

10 Sept - 11 Sept

includes taxes & fees

Hotels in Winchester with star rating

Frequently asked questions

What's the weather like in Winchester?

The hottest months are usually July and August, with an average temperature of 22°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Winchester is 1172 mm.

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Book Hotels in Winchester on Expedia.com

Find hotels in Winchester, VA from 1.916.537 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winchester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winchester hotels

1. La Quinta Inn & Suites by Wyndham Winchester

2. Microtel Inn & Suites by Wyndham Winchester

3. Spark by Hilton Winchester

4. Hampton Inn Front Royal

5. TRU By Hilton Winchester

6. Travelodge by Wyndham Winchester

7. Quality Inn Winchester

8. Comfort Inn & Suites Winchester

9. Holiday Inn Winchester Se-Historic Gateway by IHG

10. Fairfield Inn & Suites by Marriott Winchester

11. The George Washington Hotel, A Wyndham Grand Hotel

12. Ramada by Wyndham Strasburg/Shenandoah Valley

13. DoubleTree by Hilton Front Royal Blue Ridge Shadows

14. Hampton Inn Winchester N/Conference Center, VA

15. Motel 6 Front Royal, VA

16. SpringHill Suites by Marriott Winchester

17. Courtyard by Marriott Winchester

18. Candlewood Suites Winchester by IHG

19. Twi-Lite Inn

20. Fairfield Inn & Suites Strasburg Shenandoah Valley

Where to stay in Winchester

Old Town Winchester

Winchester Historic District

Stay near popular Winchester attractions

Museum of the Shenandoah Valley

Shenandoah University

Apple Blossom Mall

Patsy Cline Historic House

Shenandoah Valley Discovery Museum

Rock Harbor Golf Course

Bright Box Theater

Stonewall Jackson's Headquarters

Winchester and related destinations

Top Winchester Hotel Reviews

La Quinta Inn & Suites by Wyndham Winchester

Quality Inn Winchester

SpringHill Suites by Marriott Winchester

Travelodge by Wyndham Winchester

Country Inn & Suites by Radisson, Winchester, VA

Courtyard by Marriott Winchester

Candlewood Suites Winchester by IHG

Days Inn by Wyndham Winchester

Lansdowne Resort and Spa

More cheap stays in Winchester

Quality Inn Luray

Ramada by Wyndham Strasburg/Shenandoah Valley

Quality Inn Winchester

Microtel Inn & Suites by Wyndham Winchester

Comfort Inn & Suites Winchester

Skyland

Hotels in Winchester with star rating

Frequently asked questions

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