Upperville Vacation Rentals from SAR 496: Search Short-Term Rentals

Q: What are some of the best vacation home rentals that Upperville has to offer?

Mountain View Bungalow in Front Royal : This vacation home rental outside of Upperville offers a garden, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Upperville vacation rentals

A rural landscape with a wooden fence, a building with a chimney, and a sunset in the background.

1. "The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

Markham

Melissa B.

A fenced grassy field with a clear sky and distant hills.

2. Lunar Loft, with mountain views

Bluemont

Christina C.

SAR 967 total

includes taxes & fees

26 Nov - 27 Nov

An outdoor patio with a wooden table and two chairs, surrounded by greenery and a wooden fence.

3. Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Bluemont

Leslie C.

SAR 1,288 total

includes taxes & fees

1 Dec - 2 Dec

A patio with stone flooring, a round table, and metal chairs.

4. 18th Century Stone Cottage minutes from historic Middleburg

Middleburg

Mary H.

SAR 1,474 total

includes taxes & fees

15 Nov - 16 Nov

A deck with a fire pit, outdoor furniture, and a view of the forest.

5. Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6

Linden

Andrew G.

SAR 1,643 total

includes taxes & fees

15 Nov - 16 Nov

A two-story house with a balcony, surrounded by trees and snow.

6. Cozy A frame cabin in quaint Front Royal. Dog friendly

Front Royal

Kye Y.

SAR 1,010 total

includes taxes & fees

22 Nov - 23 Nov

A hot tub on a deck with a white railing and greenery in the background.

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

Front Royal

P H.

A covered porch with an American flag, a view of a green lawn, and a pathway.

8. 1910 Farmhouse on 6 Acres • VA Wine Country

Marshall

Erick U.

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

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

Middleburg

Claudia G.

SAR 971 total

includes taxes & fees

22 Nov - 23 Nov

A wooden cabin with a deck and string lights.

10. Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries

Front Royal

Steven D.

Local wineries, breweries, and small-town charm in Front Royal

11. Mountain Views w/Hot Tub, 95” TV & Trail Access

Shenandoah Farms

Matt F.

A kitchen with a large island, wooden cabinets, a microwave, a coffee maker, and a window above the sink.

12. super cosy cottage with high speed internet!

Middleburg

Lynette

SAR 1,121 total

includes taxes & fees

1 Dec - 2 Dec

A covered outdoor deck with a fire pit, seating, and a view of the landscape.

13. Mountain Cabin Retreat | Hot Tub & Foosball |

Front Royal

Christine T.

SAR 1,600 total

includes taxes & fees

1 Dec - 2 Dec

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

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

Front Royal

Carla M.

SAR 944 total

includes taxes & fees

10 Dec - 11 Dec

A wooden deck with a hot tub, steps, and a view of a forest.

15. The Foxwood Cabin | Hot Tub, Screened Porch, Grill

Front Royal

Roland C.

A covered porch with stone flooring, two chairs, a rug, and a glass door with a black frame.

16. Spacious Modern Home on Middleburg Horse Farm

Middleburg

Denise B.

SAR 2,144 total

includes taxes & fees

15 Nov - 16 Nov

A wooden deck with outdoor furniture and a fire pit, surrounded by trees and a railing.

17. Shenandoah Twilight | Sunset Views w/ Hot Tub + Fire Table, Near Skyline Drive

Front Royal

casey p.

A cozy outdoor seating area with a sofa and a fire pit, wooden deck, and a glass door leading to an interior space.

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

Linden

Scott M.

SAR 1,264 total

includes taxes & fees

19 Nov - 20 Nov

A wooden cabin with a porch, surrounded by trees and a gravel path.

19. The Grape Escape: Sip, Relax & Unwind in a Virginia Wine Country A-Frame

Linden

Steven B.

SAR 1,312 total

includes taxes & fees

1 Dec - 2 Dec

A two-story house with a balcony, a hot tub, and a circular wooden structure.

20. Luxury Mountain Retreat w/ Valley Views, Hot Tub

Front Royal

Charlie R.

View all properties

Find vacation rentals that suit your style

Top Upperville Hotel Reviews

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

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

A bar area with wooden shelves stocked with bottles, a bar counter, and leather bar stools.

L'Auberge Provencale Inn & Restaurant

Boyce

10/10 Excellent

Mary

Inn at Evergreen

Haymarket

10/10 Excellent

Jeff

An outdoor patio with a stone fire feature, wicker furniture, and a building with large windows and a stone facade.

TownePlace Suites by Marriott Front Royal

Front Royal

10/10 Excellent

Joseph

An indoor swimming pool with clear glass walls, a tiled floor, and a view of greenery outside.

Hampton Inn Front Royal

Front Royal

10/10 Excellent

Laura

A modern dining area with round tables and wicker chairs, large windows, and a wooden ceiling.

Hilton Garden Inn Haymarket

Haymarket

10/10 Excellent

Anonymous traveler

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

La Quinta Inn & Suites by Wyndham Winchester

Winchester

10/10 Excellent

Roberta

A gazebo with a paved pathway leading to it, surrounded by greenery and a sunset in the background.

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 patio with brick walls, tables, chairs, and string lights.

The George Washington Hotel, A Wyndham Grand Hotel

Old Town Winchester

10/10 Excellent

Kelley Ann

A hotel with a prominent "HOME" sign, outdoor seating area, and a covered entrance.

Home2 Suites by Hilton Charles Town

Charles Town

10/10 Excellent

Tommy

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

TRU By Hilton Winchester

Winchester

10/10 Excellent

Eddy

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

Microtel Inn & Suites by Wyndham Winchester

Winchester

10/10 Excellent

Elizabeth

Frequently Asked Questions

Can I find a vacation rental in Upperville?

Yes, we offer vacation rentals close to well known attractions in Upperville, or you can go with a more secluded option if you're looking for relaxation. Upperville is known for its restaurants.

What are some of the best vacation home rentals that Upperville has to offer?

Mountain View Bungalow in Front Royal: This vacation home rental outside of Upperville offers a garden, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Upperville?

Choose from 7 Expedia vacation rentals in Upperville for a memorable vacation.

What can I see and do in Upperville?

While exploring the area, visit family-friendly sights like Great Country Farms, or get outside and enjoy nature at Upperville Park. Sky Meadows State Park and Delaplane Cellars are a couple of places you'll find in the larger area.

What are vacation rentals like in Upperville?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Upperville. Vacation rentals offer extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a family trip or a small group gathering.

Upperville Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Upperville vacation rentals

1. "The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country

2. Lunar Loft, with mountain views

3. Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

4. 18th Century Stone Cottage minutes from historic Middleburg

5. Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6

6. Cozy A frame cabin in quaint Front Royal. Dog friendly

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

8. 1910 Farmhouse on 6 Acres • VA Wine Country

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

10. Custom Log Cabin•Hot Tub• Friendly•Close to River,Wineries,Breweries

11. Mountain Views w/Hot Tub, 95” TV & Trail Access

12. super cosy cottage with high speed internet!

13. Mountain Cabin Retreat | Hot Tub & Foosball |

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

15. The Foxwood Cabin | Hot Tub, Screened Porch, Grill

16. Spacious Modern Home on Middleburg Horse Farm

17. Shenandoah Twilight | Sunset Views w/ Hot Tub + Fire Table, Near Skyline Drive

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

19. The Grape Escape: Sip, Relax & Unwind in a Virginia Wine Country A-Frame

20. Luxury Mountain Retreat w/ Valley Views, Hot Tub

Find vacation rentals that suit your style

Top Upperville Hotel Reviews

Goodstone Inn & Restaurant

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Upperville?

What are some of the best vacation home rentals that Upperville has to offer?

How many vacation rentals are there in Upperville?

What can I see and do in Upperville?

What are vacation rentals like in Upperville?