Upperville Holiday Rentals, Virginia: Private House Rentals

A sign for the Village of UPPERVILLE with a 'Please drive slowly' message.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Upperville

Pet friendly

Apartment

Pool

Condo

Family friendly

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Upperville hotels

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

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

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

An indoor swimming pool with clear water, blue lounge chairs, and a wooden ceiling.

1. La Quinta Inn & Suites by Wyndham Winchester

Winchester

Earl

2.692.300 ₫

2.996.530 ₫ total

includes taxes & fees

27 Sept - 28 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 Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.

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

2. Microtel Inn & Suites by Wyndham Winchester

Winchester

Marcia

2.640.787 ₫

2.939.196 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

3. Fairfield Inn & Suites by Marriott Winchester

Winchester

Dawn

2.408.159 ₫

2.680.280 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

4. Comfort Inn & Suites Winchester

Winchester

John

2.432.851 ₫

2.707.764 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A swimming pool with clear water, surrounded by large windows offering views of greenery.

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

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

5. Hampton Inn Front Royal

Front Royal

Edward

3.306.182 ₫

3.679.780 ₫ total

includes taxes & fees

1 Oct - 2 Oct

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

A hotel room with two beds, a wooden headboard, a nightstand, a lamp, and a framed picture on the wall.

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

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

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

Stephens City

Kevin

2.313.288 ₫

2.574.689 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

A modern indoor space with a long wooden table and benches, surrounded by chairs and a green carpet.

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.

7. Spark by Hilton Winchester

Winchester

Peter

2.034.394 ₫

2.304.968 ₫ total

includes taxes & fees

4 Oct - 5 Oct

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 a sofa, a desk, a TV, a dresser, and a bed.

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

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

8. Travelodge by Wyndham Winchester

Winchester

john

1.793.448 ₫

1.978.251 ₫ total

includes taxes & fees

29 Sept - 30 Sept

A spacious living room with a fireplace, wooden staircase, and a bookshelf.

A Country Inn & Suites by Radisson building with a covered entrance and multiple windows.

A woman using a stationary bike in a gym with red walls and multiple exercise machines.

9. Country Inn & Suites by Radisson, Winchester, VA

Winchester

Allen

2.446.367 ₫

2.722.806 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

10. TRU By Hilton Winchester

Winchester

Kailyn

2.536.299 ₫

2.822.901 ₫ total

includes taxes & fees

4 Oct - 5 Oct

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

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

A swimming pool with lounge chairs and a changing room.

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

11. Holiday Inn Winchester Se-Historic Gateway by IHG

Winchester

Jennifer

2.677.176 ₫

3.057.673 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

12. Quality Inn Winchester

Winchester

Joseph

2.187.227 ₫

2.434.383 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A reception area with a blue door, a reception desk, and two armchairs.

A white car parked in front of a Days Inn sign.

A breakfast area with a counter, seating, and a Daybreak sign.

A motel with a covered parking area, a small lobby, and a building with a flat roof.

13. Days Inn by Wyndham Charles Town/Harpers Ferry

Charles Town

Nathaniel

1.827.498 ₫

2.065.073 ₫ total

includes taxes & fees

29 Sept - 30 Sept

An outdoor patio area with stone tables and chairs, surrounded by potted plants and umbrellas.

A dining area with a fireplace, wooden chairs, and tables set for a meal.

A garden with a wooden door, surrounded by greenery and a stone wall.

A living room with a white sofa, a wooden coffee table, a TV on a white cabinet, and a wooden staircase.

14. The Red Fox Inn & Tavern

Downtown

Margaret

10.008.999 ₫

11.410.228 ₫ total

includes taxes & fees

27 Sept - 28 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 lobby with yellow patterned chairs, a round table, a TV on the wall, and a patterned rug.

A hotel room with a large bed, a bedside table with a lamp, a small desk, and a kitchenette area.

15. Hampton Inn Winchester N/Conference Center, VA

Winchester

Michael

2.493.672 ₫

2.825.329 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A patio area with outdoor seating, a barbecue grill, and umbrellas.

A Holiday Inn Express & Suites building with a modern design, featuring a blue accent wall and a well-lit entrance.

A compact kitchen with a microwave, refrigerator, and a coffee maker. There is a dining area with a table and chairs. A blue sofa is visible in the adjacent living area.

A spacious lobby with a blue sofa, a grey couch, and a small table. There is a coffee station in the background.

16. Holiday Inn Express & Suites Leesburg - Historic District by IHG

Leesburg

Diana

2.859.120 ₫

3.287.989 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

17. DoubleTree by Hilton Front Royal Blue Ridge Shadows

Front Royal

Brian

3.175.703 ₫

3.502.800 ₫ total

includes taxes & fees

26 Oct - 27 Oct

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 modern kitchen with dark cabinets, a white countertop, a built-in microwave, and a coffee maker.

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

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

18. Candlewood Suites Winchester by IHG

Winchester

Bridget

2.521.224 ₫

2.806.096 ₫ total

includes taxes & fees

26 Oct - 27 Oct

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.

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.

19. SpringHill Suites by Marriott Winchester

Winchester

Michael

3.179.341 ₫

3.538.607 ₫ total

includes taxes & fees

4 Oct - 5 Oct

A spacious living room with a wooden floor, a large sofa, a coffee table, and a dining area with a wooden table and chairs.

A covered outdoor dining area with a glass table surrounded by chairs, a candle centerpiece, and a view of greenery through large windows.

A large, two-story house with a circular driveway, surrounded by well-maintained lawns and trees.

A gazebo with a brick pathway leading to it, surrounded by a grassy area with purple flowers.

20. Loudoun Valley Manor

Waterford

Mindi

3.898.800 ₫

4.444.632 ₫ total

includes taxes & fees

27 Sept - 28 Sept

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Upperville attractions

Upperville Park

Explore the great outdoors at Upperville Park, a lovely green space in Upperville.

See properties

Learn more about Upperville

Hunt country elegance shines at the historic Upperville Horse Show, America's oldest running exhibition where equestrians compete each June. Wander through the quaint village to discover stone buildings, antique shops, and Sky Meadows State Park's hiking trails nearby in Paris.

See all hotels in Upperville

Top Upperville Hotel Reviews

Comfort Inn & Suites Winchester

10/10 Excellent

"Very clean. Breakfast options were great. Easy off and on the freeway."

TRU By Hilton Winchester

10/10 Excellent

"Great Location & Customer Service"

Hampton Inn Front Royal

10/10 Excellent

"Conveniently located"

Travelodge by Wyndham Winchester

8/10 Good

"The shampoo/conditioner actually worked without additional conditioner. I was able to come through my hair with little issue."

Hotel Burg

10/10 Excellent

"I had high expectations based on reviews and photos and was pleasantly surprised when reality exceeded them. This hotel is stunningly beautiful and impeccably maintained. The Diana Lounge is elegant and the food was a feast for the eyes and a pleasure to the palate. The only thing missing was Ralph Lauren in person. This beautiful property was clearly inspired by him and bravo to the design team. We look forward to a return visit."

Quality Inn Winchester

10/10 Excellent

"Great"

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent

"Excellent in all aspects of the stay. My go to when visiting my son. 3rd time here and never disappointed. Staff so nice property kept up well. Beds so comfortable you don’t want to get up. Coffee always available in the lobby. Also wine available for sale. Love love it ."

La Quinta Inn & Suites by Wyndham Winchester

8/10 Good

"The hotel is beautiful. We'll maintained. The room was great with a minimalist vibe, but still well appointed. I was disappointed with the breakfast. Very basic hotel fare. Items were in separate areas so you were left searching for the food. Also tried the treadmill in the fitness center. No instructions on how to operate that particular model. Overall it was a good stay and the staff were friendly."

Clarion Inn Harpers Ferry - Charles Town

8/10 Good

"Good clean hotel, quiet night, overall pleasant experience"

More cheap stays in Upperville

Travelodge by Wyndham Winchester

160 Front Royal Pike Winchester VA

1.793.448 ₫

1.978.251 ₫ total

29 Sept - 30 Sept

includes taxes & fees

8.6/10 Excellent! (1,076 reviews)

Quality Inn Winchester

1601 Martinsburg Pike Winchester VA

2.187.227 ₫

2.434.383 ₫ total

25 Oct - 26 Oct

includes taxes & fees

9.4/10 Exceptional! (1,004 reviews)

Comfort Inn & Suites Winchester

195 Kernstown Commons Blvd Winchester VA

2.432.851 ₫

2.707.764 ₫ total

18 Oct - 19 Oct

includes taxes & fees

9.4/10 Exceptional! (1,133 reviews)

TRU By Hilton Winchester

118 Mercedes Court Winchester VA

2.536.299 ₫

2.822.901 ₫ total

4 Oct - 5 Oct

includes taxes & fees

9.2/10 Wonderful! (1,002 reviews)

Best Western Leesburg Hotel & Conference Center

726 E Market St Leesburg VA

2.465.081 ₫

2.834.843 ₫ total

18 Oct - 19 Oct

includes taxes & fees

Microtel Inn & Suites by Wyndham Winchester

150 Faraday Plaza Winchester VA

2.640.787 ₫

2.939.196 ₫ total

25 Oct - 26 Oct

includes taxes & fees

Hotels in Upperville with star rating

Frequently asked questions

What's the weather like in Upperville?

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 3°C. Average annual precipitation for Upperville is 1123 mm.

Explore a world of travel with Expedia

Book Hotels in Upperville on Expedia.com

Find hotels in Upperville, VA from 1.844.230 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Upperville

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Upperville hotels

1. La Quinta Inn & Suites by Wyndham Winchester

2. Microtel Inn & Suites by Wyndham Winchester

3. Fairfield Inn & Suites by Marriott Winchester

4. Comfort Inn & Suites Winchester

5. Hampton Inn Front Royal

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

7. Spark by Hilton Winchester

8. Travelodge by Wyndham Winchester

9. Country Inn & Suites by Radisson, Winchester, VA

10. TRU By Hilton Winchester

11. Holiday Inn Winchester Se-Historic Gateway by IHG

12. Quality Inn Winchester

13. Days Inn by Wyndham Charles Town/Harpers Ferry

14. The Red Fox Inn & Tavern

15. Hampton Inn Winchester N/Conference Center, VA

16. Holiday Inn Express & Suites Leesburg - Historic District by IHG

17. DoubleTree by Hilton Front Royal Blue Ridge Shadows

18. Candlewood Suites Winchester by IHG

19. SpringHill Suites by Marriott Winchester

20. Loudoun Valley Manor

Stay near popular Upperville attractions

Upperville Park

Learn more about Upperville

Top Upperville Hotel Reviews

Comfort Inn & Suites Winchester

TRU By Hilton Winchester

Hampton Inn Front Royal

Travelodge by Wyndham Winchester

Hotel Burg

Quality Inn Winchester

Country Inn & Suites by Radisson, Winchester, VA

La Quinta Inn & Suites by Wyndham Winchester

Clarion Inn Harpers Ferry - Charles Town

More cheap stays in Upperville

Travelodge by Wyndham Winchester

Quality Inn Winchester

Comfort Inn & Suites Winchester

TRU By Hilton Winchester

Best Western Leesburg Hotel & Conference Center

Microtel Inn & Suites by Wyndham Winchester

Hotels in Upperville with star rating

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app