Upperville, VA Villas Rentals

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Recommended hotels in Upperville

A modern house with a stone facade, large windows, and a sloped roof.

1. Goodstone Inn & Restaurant

Middleburg

Karlyn

$377 nightly

Nov 15 - Nov 16

Total with taxes and fees

A stone house with a chimney, surrounded by a well-maintained lawn and trees.

2. 18th Century Stone Cottage minutes from historic Middleburg

Middleburg

Mary H.

$366 nightly

Nov 15 - Nov 16

Total with taxes and fees

A covered outdoor seating area with wicker chairs and a patterned rug, overlooking a garden and a building.

3. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

Front Royal

P H.

$336 nightly

Nov 16 - Nov 17

Total with taxes and fees

A white building with a white door, two trash bins, and a small black object on the wall.

4. Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

Middleburg

Claudia G.

$227 nightly

Nov 22 - Nov 23

Total with taxes and fees

An outdoor patio area with multiple tables and chairs, a stone pathway, and a view of a golf course and lake.

5. Inn at Evergreen

Haymarket

Gary

$274 nightly

Dec 6 - Dec 7

Total with taxes and fees

A single-story house with a porch, a front door, and two windows.

6. Spacious Modern Home on Middleburg Horse Farm

Middleburg

Denise B.

$501 nightly

Nov 12 - Nov 13

Total with taxes and fees

A Hampton Inn with a covered entrance and a parking lot.

7. Hampton Inn Front Royal

Front Royal

Tammy

$118 nightly

Nov 19 - Nov 20

Total with taxes and fees

A terrace with tables set for a wedding, overlooking a golf course and a body of water.

8. DoubleTree by Hilton Front Royal Blue Ridge Shadows

Front Royal

Adrian

$118 nightly

Dec 6 - Dec 7

Total with taxes and fees

A residential area with a well-maintained garden, a lawn, and houses with distinct architectural styles.

9. L'Auberge Provencale Inn & Restaurant

Boyce

James

$320 nightly

Nov 17 - Nov 18

Total with taxes and fees

A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

10. Blue Mountain Cabin, secluded, perfect for couples, near main road

Front Royal

Carla M.

$221 nightly

Nov 11 - Nov 12

Total with taxes and fees

A multi-story hotel with a swimming pool, parking lot, and a landscaped area.

11. TownePlace Suites by Marriott Front Royal

Front Royal

JoEllen

$137 nightly

Nov 29 - Nov 30

Total with taxes and fees

A modern Microtel hotel by Wyndham with a blue and gray exterior, multiple windows, and a parking lot.

12. Microtel Inn & Suites by Wyndham Winchester

Winchester

Kathleen

$79 nightly

Nov 15 - Nov 16

Total with taxes and fees

13. Comfort Inn & Suites Winchester

Winchester

Donna S.

$87 nightly

Dec 1 - Dec 2

Total with taxes and fees

A hot tub with a view of a forest and a sunset.

14. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

Linden

Scott M.

$295 nightly

Nov 17 - Nov 18

Total with taxes and fees

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

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

Stephens City

Michael

$80 nightly

Dec 10 - Dec 11

Total with taxes and fees

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

16. La Quinta Inn & Suites by Wyndham Winchester

Winchester

lucy

$104 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

17. Spark by Hilton Winchester

Winchester

Albert

$65 nightly

Nov 22 - Nov 23

Total with taxes and fees

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

18. Fairfield Inn & Suites by Marriott Winchester

Winchester

Thomas

$93 nightly

Nov 15 - Nov 16

Total with taxes and fees

A Super 8 hotel with a brick facade, multiple windows, and a central entrance.

19. Super 8 by Wyndham Front Royal Near Shenandoah National Park

Front Royal

Amelia

$72 nightly

Dec 10 - Dec 11

Total with taxes and fees

An outdoor patio with a grill, seating, and string lights.

20. Home2 Suites By Hilton Winchester

Winchester

Jean

$88 nightly

Nov 22 - Nov 23

Total with taxes and fees

View all 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

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

Top reviews in Upperville

Goodstone Inn & Restaurant

Middleburg

10/10 Excellent

Adrian

A large, two-story house with a central entrance, multiple chimneys, and a well-maintained lawn with a pathway leading to the entrance.

Salamander Middleburg

Middleburg

10/10 Excellent

We stayed at the resort when the town of Middleburg has it's annual Christmas town parade so needless to say every hotel and restaurant in the area was booked way in advance. We were quickly checked in and went our room. It was beautiful, clean, big bathroom with robes and even bath salts for a soak in the nice tub. We had a first floor room with a patio and the sun was shining bright in the room. After we settled we went to see the concierge about maybe finding a dinner reservation somewhere...

MaBunny63

Inn at Evergreen

Haymarket

10/10 Excellent

Jeff

A large stone building with a white porch and multiple flags.

L'Auberge Provencale Inn & Restaurant

Boyce

10/10 Excellent

Mary

TownePlace Suites by Marriott Front Royal

Front Royal

10/10 Excellent

JoEllen

Hampton Inn Front Royal

Front Royal

10/10 Excellent

Laura

Microtel Inn & Suites by Wyndham Winchester

Winchester

10/10 Excellent

Elizabeth

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

Loudoun Valley Manor

Waterford

10/10 Excellent

My partner and I stayed here for two nights, and had a relaxing little vacation away from the bustle of D.C. Olga was a lovely host and made us feel very welcome. She cooked omelettes bright and early every morning, and always had coffee, tea, and snacks available throughout the day. There are a lot of vineyards and breweries nearby to visit, and the air-conditioned rooms were a comfortable retreat from the afternoon heat. The house was pristine, gorgeously decorated, and the view of the...

Anonymous traveler

An outdoor seating area with wicker chairs and tables, large windows, and a brick building facade.

Hilton Garden Inn Haymarket

Haymarket

10/10 Excellent

Anonymous traveler

La Quinta Inn & Suites by Wyndham Winchester

Winchester

10/10 Excellent

Roberta

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

The George Washington Hotel, A Wyndham Grand Hotel

Old Town Winchester

10/10 Excellent

Kelley Ann

A hotel with a modern design, featuring a prominent 'spark by Hilton' sign, a covered entrance, and a well-maintained outdoor area with plants and a bench.

Spark by Hilton Winchester

Winchester

10/10 Excellent

Joan

A hotel with a covered outdoor area, a parking lot, and well-maintained landscaping.

Quality Inn Winchester

Winchester

10/10 Excellent

Paul

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Villas in Upperville

Bundle & Save

OneKeyCash

Upfront pricing

Find vacation rentals that suit your style

Check prices for these dates

Recommended hotels in Upperville

1. Goodstone Inn & Restaurant

2. 18th Century Stone Cottage minutes from historic Middleburg

3. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

4. Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

5. Inn at Evergreen

6. Spacious Modern Home on Middleburg Horse Farm

7. Hampton Inn Front Royal

8. DoubleTree by Hilton Front Royal Blue Ridge Shadows

9. L'Auberge Provencale Inn & Restaurant

10. Blue Mountain Cabin, secluded, perfect for couples, near main road

11. TownePlace Suites by Marriott Front Royal

12. Microtel Inn & Suites by Wyndham Winchester

13. Comfort Inn & Suites Winchester

14. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

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

16. La Quinta Inn & Suites by Wyndham Winchester

17. Spark by Hilton Winchester

18. Fairfield Inn & Suites by Marriott Winchester

19. Super 8 by Wyndham Front Royal Near Shenandoah National Park

20. Home2 Suites By Hilton Winchester

Learn more about Upperville

Top reviews in Upperville

Goodstone Inn & Restaurant

10/10 Excellent

Frequently Asked Questions

Why book your villa in Upperville with Expedia?

How can I find cheap villas in Upperville?

Explore a world of travel with Expedia