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

Cottage

Waterpark

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Upperville 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.

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

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

1. La Quinta Inn & Suites by Wyndham Winchester

Winchester

Raquel

Rp1.922.978

Rp2.140.274 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 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.

2. Microtel Inn & Suites by Wyndham Winchester

Winchester

Ricky

Rp1.524.269

Rp1.696.511 total

includes taxes & fees

8 Sept - 9 Sept

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

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.

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

3. Fairfield Inn & Suites by Marriott Winchester

Winchester

Michael

Rp1.634.531

Rp1.819.234 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 a television, desk, chair, sofa, and kitchenette.

4. Comfort Inn & Suites Winchester

Winchester

Sandra

Rp1.637.178

Rp1.822.180 total

includes taxes & fees

4 Oct - 5 Oct

An indoor swimming pool with clear blue 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

Timothy

Rp2.155.500

Rp2.399.071 total

includes taxes & fees

28 Sept - 29 Sept

A large, multi-story building with a symmetrical facade, multiple chimneys, and a central entrance with columns.

A spacious lobby with a central coffee table, seating arrangements, and a fireplace.

A picnic setup with a cheese board, grapes, and a glass of white wine on a wooden table, surrounded by lush greenery and a pergola.

A swimming pool with lounge chairs and a sunset view.

6. Salamander Resort And Spa

Middleburg

Wayne

Rp12.154.313

Rp14.843.465 total

includes taxes & fees

8 Sept - 9 Sept

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

7. Quality Inn Winchester

Winchester

Scott

Rp1.409.596

Rp1.568.880 total

includes taxes & fees

13 Sept - 14 Sept

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

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

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

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

8. TRU By Hilton Winchester

Winchester

Gerley

Rp1.576.842

Rp1.755.025 total

includes taxes & fees

13 Sept - 14 Sept

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

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.

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

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

Stephens City

Kevin

Rp1.552.496

Rp1.727.928 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 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.

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

10. Travelodge by Wyndham Winchester

Winchester

Thomas

Rp1.340.792

Rp1.478.929 total

includes taxes & fees

6 Sept - 7 Sept

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

A poolside area with lounge chairs and a stack of towels on a table.

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

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

Winchester

Nancy

Rp1.752.203

Rp1.950.202 total

includes taxes & fees

27 Sept - 28 Sept

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

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

12. Days Inn by Wyndham Charles Town/Harpers Ferry

Charles Town

Nathaniel

Rp1.240.409

Rp1.401.661 total

includes taxes & fees

8 Sept - 9 Sept

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 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 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.

13. Spark by Hilton Winchester

Winchester

Alexandra

Rp1.360.198

Rp1.541.104 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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.

14. The Red Fox Inn & Tavern

Downtown

Margaret

Rp6.793.581

Rp7.744.662 total

includes taxes & fees

28 Sept - 29 Sept

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

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.

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

15. Hampton Inn Winchester N/Conference Center, VA

Winchester

Jackie

Rp1.866.171

Rp2.114.372 total

includes taxes & fees

13 Sept - 14 Sept

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

A hotel lobby with seating areas, a reception desk, and a large window.

A spacious lobby with a piano, a reception desk, and a large window.

A hotel room with a kitchenette, a dining area, a large wooden wardrobe, and a bathroom with a sink and mirror.

16. Best Western Leesburg Hotel & Conference Center

Leesburg

Edward

Rp1.673.167

Rp1.924.141 total

includes taxes & fees

14 Sept - 15 Sept

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

A Baymont Inn & Suites with a blue roof, a well-lit entrance, and a landscaped driveway.

A reception area with a wooden reception desk, a seating area with chairs and a table, and a glass door entrance.

A hotel room with two beds, a chair, a nightstand, and a wall-mounted lamp.

17. Baymont by Wyndham Warrenton

Warrenton

Jon

Rp1.224.708

Rp1.314.111 total

includes taxes & fees

15 Sept - 16 Sept

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 lobby with a large dining area, wooden accents, and contemporary lighting fixtures.

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

18. SpringHill Suites by Marriott Winchester

Winchester

Michael

Rp2.157.969

Rp2.401.819 total

includes taxes & fees

13 Sept - 14 Sept

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

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

A spacious lobby with a stone fireplace, blue upholstered sofas, and a chandelier.

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

19. DoubleTree by Hilton Front Royal Blue Ridge Shadows

Front Royal

Alok

Rp2.155.500

Rp2.377.517 total

includes taxes & fees

13 Sept - 14 Sept

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

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

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.

20. Courtyard by Marriott Winchester

Winchester

David

Rp1.889.458

Rp2.102.967 total

includes taxes & fees

13 Sept - 14 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

"Friendly greeting, excellent, spacious room, clean, comfortable beds. Breakfast was nice and plenty of parking."

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent

"Great find! It’s new, it’s clean, great staff! Going again soon a stop on a longer trip into Virginia. It’s right off the highway!"

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent

"We chose Old Town Winchester and stayed at The George Washington Hotel as our gathering spot for High school girl friends The Hotel was beautiful ,our rooms big enough plus having a sm scale table with 2 chairs ,the bathroom very roomy,beds were very comfortable and the staff very accommodating and welcoming The amenities at the hotel met our needs perfectly ! It was really nice to be in a walkable area with many shops and restaurants ,pubs .No complaints from 5 women in our group 😁"

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent

"Clean room quiet front desk employees are always awesome !!"

Quality Inn Winchester

10/10 Excellent

"Convenient and surprisingly nice for the price"

Hotel Burg

10/10 Excellent

"Great property and the staff is fantastic.!!"

Best Western Leesburg Hotel & Conference Center

8/10 Good

"Staff was pleasant and very accomadating. Breakfast was disappointing...would have appreciated some yogurt and more fruit options and a few tea bags choices. But area was clean and pleasant. My friend's room facing the poolside of the building was updated and had better AC control. My room facing the parking lot had an AC that was loud making it difficult to sleep. But overall a great experience for 3 nights that was very reasonable! Will stay there again!"

DoubleTree by Hilton Front Royal Blue Ridge Shadows

10/10 Excellent

"The rooms were clean and well-maintained. The hotel has a convenient location to shopping and dining options. The public spaces are beautiful and comfortable. I rented a meeting room for a Celebration of Life gathering and used the hotel's catering service. The food was excellent and the staff was professional and helpful. The hotel restaurant wasn't great for breakfast, as the service was slow and the oatmeal was served undercooked. However, dinner was fine."

More cheap stays in Upperville

Red Roof Inn Winchester, VA

991 Millwood Pike Winchester VA

Rp1.225.943

Rp1.364.432 total

8 Sept - 9 Sept

includes taxes & fees

7.4/10 Good! (1,001 reviews)

Quality Inn Winchester

1601 Martinsburg Pike Winchester VA

Rp1.409.596

Rp1.568.880 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

Rp1.524.269

Rp1.696.511 total

8 Sept - 9 Sept

includes taxes & fees

Comfort Inn & Suites Winchester

195 Kernstown Commons Blvd Winchester VA

Rp1.637.178

Rp1.822.180 total

4 Oct - 5 Oct

includes taxes & fees

9.4/10 Exceptional! (1,126 reviews)

Best Western Leesburg Hotel & Conference Center

726 E Market St Leesburg VA

Rp1.673.167

Rp1.924.141 total

14 Sept - 15 Sept

includes taxes & fees

Hampton Inn Front Royal

9800 Winchester Rd Front Royal VA

Rp2.155.500

Rp2.399.071 total

28 Sept - 29 Sept

includes taxes & fees

Frequently asked questions

Where is the best place to stay in Upperville?

Located 22.8 mi (36.7 km) from the heart of Upperville, Lansdowne Resort and Spa is a top choice for your stay, based on our traveller data. Two other options for your trip to the area are Salamander Resort And Spa and Spark by Hilton Winchester. See all available top hotels, or vacation rentals in Upperville.

If I need to cancel my hotel reservation in Upperville, will I receive a refund?

Yes, you'll find most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If your reservation is non-refundable, you might be able to still cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Upperville.

What are some accommodation options with pools in Upperville?

Lansdowne Resort and Spa: Features a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Salamander Resort And Spa and Holiday Inn Winchester Se-Historic Gateway by IHG are a couple of other choices with an on-site pool. View all hotels with pools in Upperville.

What's it like to stay in Upperville?

Visitors can enjoy all that Upperville has to offer, including its restaurants. In Upperville, there are 8 hotels and other accommodation options to choose from. Find out more about Upperville.

What should I see while I'm in Upperville?

A couple of favourite places to visit are Upperville Park and Sky Meadows State Park. You'll also find Delaplane Cellars and Glenwood Park in the area. Take a look at what more there is to see and do in Expedia's Upperville guide.

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

More ways to book

Book Hotels in Upperville on Expedia.com

Find hotels in Upperville, VA from Rp1.235.271

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. Salamander Resort And Spa

7. Quality Inn Winchester

8. TRU By Hilton Winchester

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

10. Travelodge by Wyndham Winchester

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

12. Days Inn by Wyndham Charles Town/Harpers Ferry

13. Spark by Hilton Winchester

14. The Red Fox Inn & Tavern

15. Hampton Inn Winchester N/Conference Center, VA

16. Best Western Leesburg Hotel & Conference Center

17. Baymont by Wyndham Warrenton

18. SpringHill Suites by Marriott Winchester

19. DoubleTree by Hilton Front Royal Blue Ridge Shadows

20. Courtyard by Marriott Winchester

Stay near popular Upperville attractions

Upperville Park

Learn more about Upperville

Top Upperville Hotel Reviews

Comfort Inn & Suites Winchester

Holiday Inn Winchester Se-Historic Gateway by IHG

The George Washington Hotel, A Wyndham Grand Hotel

La Quinta Inn & Suites by Wyndham Winchester

Quality Inn Winchester

Hotel Burg

Best Western Leesburg Hotel & Conference Center

DoubleTree by Hilton Front Royal Blue Ridge Shadows

More cheap stays in Upperville

Red Roof Inn Winchester, VA

Quality Inn Winchester

Microtel Inn & Suites by Wyndham Winchester

Comfort Inn & Suites Winchester

Best Western Leesburg Hotel & Conference Center

Hampton Inn Front Royal

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app