Upperville, VA Cottages from AED 367

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Our top choices for Upperville cottages

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

1. 18th Century Stone Cottage minutes from historic Middleburg

Middleburg

Mary H.

AED 1,450 total

includes taxes & fees

16 Nov - 17 Nov

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

2. Mountain View Cottage with Hot Tub and River Views

Front Royal

"We enjoyed our stay and certainly return. Our group was 2 couples and 2 children.Everyone had enough space to be comfortable. The view is beautiful so we enjoyed our time at the house. While in the area, we visited Skyline Caverns and the Shenandoah River. I did have a challenging time getting Door Dash to the house. After 30 minutes of seeing the driver in the neighborhood we got in the car to track down the driver. Her cell service was poor so we were unable to communicate. If I ordered...

MaryBeth C.

AED 2,833 total

includes taxes & fees

21 Nov - 22 Nov

3. Mountaintop Cottage | Private Hot Tub

Front Royal

Kevin D.

AED 2,596 total

includes taxes & fees

21 Nov - 22 Nov

A hot tub on an outdoor deck with a view of trees and hills.

4. Mountain View Cottage | Hot Tub & Game Room

Front Royal

Katia R.

AED 2,470 total

includes taxes & fees

23 Nov - 24 Nov

A covered porch with a table and chairs, large windows, and a ceiling fan.

5. Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA

Front Royal

AED 1,830 total

includes taxes & fees

5 Nov - 6 Nov

A covered deck with a table and chairs, overlooking a river and autumn foliage.

6. Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Harpers Ferry

Lindy K.

AED 1,820 total

includes taxes & fees

18 Nov - 19 Nov

A hot tub on a deck with a view of a lake and forest.

7. Peaceful Lakefront Cottage with Mountain Views!

Harpers Ferry

Tara G.

AED 1,619 total

includes taxes & fees

18 Nov - 19 Nov

A modern building with large windows, a deck, and a stone wall.

8. Woodsy Retreat with a Hot Tub and Seasonal Views!

Harpers Ferry

Rebecca N.

AED 1,695 total

includes taxes & fees

15 Nov - 16 Nov

A hot tub with a view of a forested landscape during sunset.

9. Cottage w/ Hot Tub and 100-Mile Valley Views!

Harpers Ferry

Keri L.

AED 1,608 total

includes taxes & fees

16 Nov - 17 Nov

A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

10. Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Front Royal

Hailey

AED 1,449 total

includes taxes & fees

8 Nov - 9 Nov

A covered outdoor area with a hot tub, wooden benches, and a view of a snowy landscape with trees and a fence.

11. The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

Hamilton

Theresa R.

AED 1,378 total

includes taxes & fees

5 Nov - 6 Nov

A single-story house with a porch, a stone pathway leading to the entrance, and a clear sky.

12. Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Front Royal

Jake M.

AED 752 total

includes taxes & fees

8 Nov - 9 Nov

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

13. Renovated 3B/3B Home | Downtown | Private Fire Pit

Leesburg's Old and Historic District

Eric D S.

AED 2,236 total

includes taxes & fees

30 Nov - 1 Dec

A stone house with a white picket fence, a front porch, and potted plants.

14. Cottage w/ Furnished Patio & Garden: Dtwn Leesburg

Leesburg's Old and Historic District

Corky F.

AED 2,420 total

includes taxes & fees

22 Nov - 23 Nov

15. Cottage w/ Furnished Patio & Garden: Dtwn Leesburg

Leesburg's Old and Historic District

AED 2,494 total

includes taxes & fees

22 Nov - 23 Nov

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

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

Goodstone Inn & Restaurant

Middleburg

10/10 Excellent

Adrian

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

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

L'Auberge Provencale Inn & Restaurant

Boyce

10/10 Excellent

Mary

A large, historic building with a formal entrance, surrounded by well-maintained lawns and flowering trees.

Inn at Evergreen

Haymarket

10/10 Excellent

Jeff

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

TownePlace Suites by Marriott Front Royal

Front Royal

10/10 Excellent

JoEllen

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

Hampton Inn Front Royal

Front Royal

10/10 Excellent

Laura

A brick building with a sign reading "HOULIHAN'S RESTAURANT + BAR".

DoubleTree by Hilton Front Royal Blue Ridge Shadows

Front Royal

10/10 Excellent

Adrian

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

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

A modern building with a brick facade, large windows, and a covered entrance area.

Hilton Garden Inn Haymarket

Haymarket

10/10 Excellent

Anonymous traveler

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

Fairfield Inn & Suites by Marriott Winchester

Winchester

10/10 Excellent

Martina

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 traditional Tudor-style house with a pond in the foreground, surrounded by well-maintained gardens and trees.

Hillbrook Inn

Charles Town

10/10 Excellent

This is an Inn in a very rural area. It is very peaceful and this was much needed to quiet the mind. I went on the verge of the leaves changing in the fall so it was quite beautiful with changing leaves but still green grass and some plants blooming. I brought my small dog in this solo trip and it was a nice touch to leave a couple of milk bones in the room for him. I didn't go to the dining area for breakfast or dinner so I can't comment of this portion.

Patti

An outdoor patio area with wicker furniture, a fire pit, and a view of the parking lot.

Home2 Suites by Hilton Charles Town

Charles Town

10/10 Excellent

Tommy

A two-story house with a front porch, American flags, and a mailbox.

The Carriage Inn B&B

Charles Town

10/10 Excellent

retired teacher

Frequently Asked Questions

Why book your cottage in Upperville with Expedia?

Reserving a cottage in Upperville is as simple as clicking on your travel dates and selecting your ideal place for a vacation in the outdoors. From ritzy retreats to affordable stays and cottages that come with amenities like laundry facilities, Expedia has something for all styles. As for the best offers around? We've got them too!

How can I find cheap cottages in Upperville?

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Search Cottages in Upperville

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Upperville cottages

1. 18th Century Stone Cottage minutes from historic Middleburg

2. Mountain View Cottage with Hot Tub and River Views

3. Mountaintop Cottage | Private Hot Tub

4. Mountain View Cottage | Hot Tub & Game Room

5. Cozy Cottage with Hot Tub, Fire Pit and Sunroom - Loaded with Modern Touches in Front Royal, VA

6. Art Docko - Lakefront Artist Retreat w/ Hot Tub!

7. Peaceful Lakefront Cottage with Mountain Views!

8. Woodsy Retreat with a Hot Tub and Seasonal Views!

9. Cottage w/ Hot Tub and 100-Mile Valley Views!

10. Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

11. The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

12. Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

13. Renovated 3B/3B Home | Downtown | Private Fire Pit

14. Cottage w/ Furnished Patio & Garden: Dtwn Leesburg

15. Cottage w/ Furnished Patio & Garden: Dtwn Leesburg

Learn more about Upperville

Top reviews in Upperville

Goodstone Inn & Restaurant

10/10 Excellent

Frequently Asked Questions

Why book your cottage in Upperville with Expedia?

How can I find cheap cottages in Upperville?

Explore a world of travel with Expedia