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

Holiday Homes in Upperville

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Upperville holiday homes

Dining

1. Valley View Farmhouse · Hot Tub, Fenced Pasture

Valley View Farmhouse · Hot Tub, Fenced Pasture
Amissville
The price is €358
includes taxes & fees
24 Aug - 25 Aug
Valley View Farmhouse · Hot Tub, Fenced Pasture
Exterior

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

Mountain Views w/Hot Tub, 95” TV & Trail Access
Shenandoah Farms
The price is €324
includes taxes & fees
4 Aug - 5 Aug
Mountain Views w/Hot Tub, 95” TV & Trail Access
Exterior

3. Charming 3BR Farmhouse • Wine Country Getaway

Charming 3BR Farmhouse • Wine Country Getaway
Marshall
9.6 out of 10, Exceptional, (5 reviews)
"If we managed to do everything, sing, dance, play, we loved the comfortable place for us"
United States
Erick U.
The price is €343
includes taxes & fees
1 Sept - 2 Sept
Charming 3BR Farmhouse • Wine Country Getaway
Interior

4. Bluemont home just minutes to wineries, breweries, hiking and more!

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
10.0 out of 10, Exceptional, (1 review)
"Amazingly comfortable place to call home for a few days with plenty of room for activities if you have to stay in! Bedrooms were lovely as were the bathrooms. Updated and very clean!!!! Host was extremely responsive and very easy to work with!! Bonus to bring our pup with us for the stay."
United States
K O.
The price is €313
includes taxes & fees
2 Sept - 3 Sept
Bluemont home just minutes to wineries, breweries, hiking and more!
TV, offices

5. Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom
Front Royal
9.0 out of 10, Wonderful, (31 reviews)
"The house itself was clean, the beds are comfortable, and it is in a nice, quiet, and private location. The property manager was very pleasant and responsed to any questions or concerns quickly. "
United States
Elissa S.
The price is €273
includes taxes & fees
9 Aug - 10 Aug
Mountain home w/ hot tub & sunroom
Coffee/tea maker, fridge, microwave, oven

6. Spacious Modern Home on Middleburg Horse Farm

Spacious Modern Home on Middleburg Horse Farm
Middleburg
10.0 out of 10, Exceptional, (20 reviews)
"Perfect for a mother and daughter get away. Peaceful and quiet. Short distance to Middleburg. Looking forward to staying here again. Already planning another trip with the whole family at Thanksgiving!"
United States
Denise B.
The price is €432
includes taxes & fees
24 Aug - 25 Aug
Spacious Modern Home on Middleburg Horse Farm
Property grounds

7. 4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
Harpers Ferry
9.8 out of 10, Exceptional, (7 reviews)
"House was beautiful and fully equipped for our stay. The host was very communicative and we really enjoyed our time here. If in the area again would definitely stay here. "
United States
Maeve K.
The price is €381
includes taxes & fees
5 Aug - 6 Aug
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
Outdoor dining

8. Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Harpers Ferry
9.8 out of 10, Exceptional, (9 reviews)
"A wonderfully equipped home in a lovely location. Everything you could ever need was on hand. "
United States
alison m.
The price is €211
includes taxes & fees
10 Aug - 11 Aug
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Coffee/tea maker, fridge, microwave, oven

9. Historic Farmhouse, Fully Renovated in Fall 2023

Historic Farmhouse, Fully Renovated in Fall 2023
Loudoun County
9.8 out of 10, Exceptional, (10 reviews)
"We had a great stay. House is beautiful and clean and owner was highly responsive. "
United States
Michele B.
The price is €400
includes taxes & fees
1 Sept - 2 Sept
Historic Farmhouse, Fully Renovated in Fall 2023
Smart TV, books, computer monitors

10. Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (36 reviews)
"Great location, clean and comfortable. Would absolutely stay here again or recommend it to others. "
United States
Lauren S.
The price is €269
includes taxes & fees
5 Aug - 6 Aug
Leesburg Hideaway- King Bed + Private Backyard
Coffee/tea maker, fridge, oven, stovetop

11. Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
10.0 out of 10, Exceptional, (1 review)
"Nice place for a day trip to the casino."
United States
Joshua S.
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Terrace/patio

12. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (34 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is €197
includes taxes & fees
11 Aug - 12 Aug
Mountain View Bungalow in Front Royal
Smart TV, fireplace

13. Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Harpers Ferry
10.0 out of 10, Exceptional, (9 reviews)
"Welcoming host, great place!"
United States
Amanda M.
The price is €308
includes taxes & fees
31 Aug - 1 Sept
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Interior

14. Stone Cabin on Valley View: Fire Pit + Hot Tub

Stone Cabin on Valley View: Fire Pit + Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful scenery! Beautiful home! Wonderful hosts!"
United States
Brian S.
The price is €327
includes taxes & fees
1 Sept - 2 Sept
Stone Cabin on Valley View: Fire Pit + Hot Tub
Smart TV, fireplace, DVD player, books

15. Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Harpers Ferry
9.6 out of 10, Exceptional, (109 reviews)
"Wonderful place to stay. Comfotable beds and big enough for a large crowd. The property owners are incredibly kind and responsive. Our family loved our stay. "
United States
Jenn C.
The price is €364
includes taxes & fees
26 Aug - 27 Aug
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
3 bedrooms, desk, iron/ironing board, travel cot

16. Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV

Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
Harpers Ferry
10.0 out of 10, Exceptional, (13 reviews)
"Nice modern place with great amenities. Fenced yard was great for the pooches."
United States
John M.
The price is €366
includes taxes & fees
10 Aug - 11 Aug
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
Interior

17. 4BR Golf Retreat | 3 Courses | Pool Table

4BR Golf Retreat | 3 Courses | Pool Table
Front Royal
10.0 out of 10, Exceptional, (1 review)
"Home was clean and looked like it had recently been remodeled/updated. The host was very responsive and when the oven wasn't working properly, they went to Lowes and purchased a new one immediately! Made our short trip much easier not having to eat out or find a last minute option for our kids/babysitter on Friday evening. We were only in town from Thursday-Sunday, and it was perfect for the 5 of us. The pool table was a fun addition for the kids. The only minor complaint I have is that I wish I...
United States
Crystal H.
The price is €484
includes taxes & fees
3 Sept - 4 Sept
4BR Golf Retreat | 3 Courses | Pool Table
Outdoor dining

18. Farmhouse Retreat Sleeps 6, Yard for Tents, Near River + C&O Canal

Farmhouse Retreat Sleeps 6, Yard for Tents, Near River + C&O Canal
Harpers Ferry
7.2 out of 10, Good, (17 reviews)
"We had a great stay. Good location, close to Leesburg, Frederick, and Harper's Ferry center.The house was as described."
United States
Gwenaelle M.
The price is €287
includes taxes & fees
1 Sept - 2 Sept
Farmhouse Retreat Sleeps 6, Yard for Tents, Near River + C&O Canal
Bar (on property)

19. Main Street USA -- Walk to Everything

Main Street USA -- Walk to Everything
Purcellville
9.6 out of 10, Exceptional, (7 reviews)
"The property was great! Very clean and walkable to town. We had a wonderful time and Joe was great to work with! We would absolutely love to stay here again!"
United States
melissa b.
The price is €636
includes taxes & fees
2 Sept - 3 Sept
Main Street USA -- Walk to Everything
Property grounds

20. Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
Harpers Ferry
7.4 out of 10, Good, (28 reviews)
"The inside was well done and clean. Even though the neighbors are close, they were quiet. My husband and I were able to relax in a comfortable setting."
United States
Melissa H.
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Upperville Hotel Reviews

Best Western Leesburg Hotel & Conference Center

Best Western Leesburg Hotel & Conference Center

10/10 Excellent
"Nice hotel, seems recently renovated so all was is very good shape. Staff was helpful and friendly. The pool was nice, well kept and working."
Katherine 2-night trip
Posted 1 hour ago
Best Western Leesburg Hotel & Conference Center

Find out more about Upperville

Upperville Holiday Homes information

Number of reviews
183
Accommodation
252 Holiday Homes
Lowest Price
€197
Highest Price
€636