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Our top choices for Upperville vacation homes

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (34 reviews)
"The host was great in communicating check in and check out instructions! We appreciated being able to park in the driveway and the fenced in back yard was also a nice amenity. Would definitely stay here again!"
United States
Katherine s.
The price is AED 698
AED 1,398 total
includes taxes & fees
20 May - 21 May
Leesburg Hideaway- King Bed + Private Backyard

Mountain cottage w/hot tub & lake

Mountain cottage w/hot tub & lake
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 AED 703
AED 1,260 total
includes taxes & fees
5 May - 6 May
Mountain cottage w/hot tub & lake

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, (7 reviews)
"Welcoming host, great place!"
United States
Amanda M.
The price is AED 562
AED 1,455 total
includes taxes & fees
29 Apr - 30 Apr
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (23 reviews)
"We enjoyed our stayed so much! This location is perfect. This property is so clean. "
United States
Nicole Z.
The price is AED 496
AED 809 total
includes taxes & fees
6 May - 7 May
Mountain View Bungalow in Front Royal

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, (12 reviews)
"Beautiful scenery! Beautiful home! Wonderful hosts!"
United States
Brian S.
The price is AED 606
AED 1,407 total
includes taxes & fees
29 Apr - 30 Apr
Stone Cabin on Valley View: Fire Pit + Hot Tub

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Harpers Ferry
10.0 out of 10, Exceptional, (25 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
The price is AED 538
AED 1,478 total
includes taxes & fees
3 May - 4 May
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

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

Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location
Harpers Ferry
7.6 out of 10, Good, (27 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.
The price is AED 509
AED 1,098 total
includes taxes & fees
5 May - 6 May
Peaceful Single-Level Retreat, Near Harpers Ferry, Easy Access + Prime Location

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (40 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is AED 588
AED 1,191 total
includes taxes & fees
29 Apr - 30 Apr
Newly renovated Farm cottage with Mountain views

Quaint Royal Cottage @ Historic Leesburg

Quaint Royal Cottage @ Historic Leesburg
Leesburg's Old and Historic District
10.0 out of 10, Exceptional, (10 reviews)
"Great location in a great town!"
United States
Gigi D.
Quaint Royal Cottage @ Historic Leesburg

Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.4 out of 10, Exceptional, (6 reviews)
"Nice house in a good central location. "
United States
Mitchell V.
The price is AED 727
AED 1,244 total
includes taxes & fees
29 Apr - 30 Apr
Cameron Charmer pristine downtown apt with double master suites

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

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
The price is AED 591
AED 1,216 total
includes taxes & fees
29 Apr - 30 Apr
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!
Charles Town
9.6 out of 10, Exceptional, (69 reviews)
"Nice quiet view, able to sit on deck for hours and talk. Close to restaurants, and stores. Had a great stay."
United States
Paul M.
The price is AED 367
AED 1,480 total
includes taxes & fees
11 May - 12 May
Terra Alta - Incredible River Views and Hot Tub!

Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country

Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country
Marshall
9.8 out of 10, Exceptional, (29 reviews)
"Everything was great "
United States
James A.
The price is AED 1,649
AED 1,993 total
includes taxes & fees
29 Apr - 30 Apr
Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country

Cottage on King | Charming Historic Leesburg Home

Cottage on King | Charming Historic Leesburg Home
Leesburg's Old and Historic District
9.6 out of 10, Exceptional, (70 reviews)
"the cottage had everything we needed. "
United States
christa S.
The price is AED 1,121
AED 1,944 total
includes taxes & fees
6 May - 7 May
Cottage on King | Charming Historic Leesburg Home

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
Linden
10.0 out of 10, Exceptional, (26 reviews)
"Lovely home and great view. Host communication was fabulous. The welcome snacks, wine, and toiletries were very sweet. "
United States
Kathryn B.
The price is AED 695
AED 1,443 total
includes taxes & fees
5 May - 6 May
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

Huckleberry Hills | Hot Tub & Fire Pit & Dogs

Huckleberry Hills | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.6 out of 10, Exceptional, (10 reviews)
"The house was a great location for what we were lookin for, the kids loved the hot Tub and being able to explore"
United States
Bryan S.
The price is AED 367
AED 1,500 total
includes taxes & fees
30 Apr - 1 May
Huckleberry Hills | Hot Tub & Fire Pit & Dogs

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
9.6 out of 10, Exceptional, (4 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 AED 459
AED 1,615 total
includes taxes & fees
12 May - 13 May
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

The Cottage on Royal - Historic Leesburg Home

The Cottage on Royal - Historic Leesburg Home
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (19 reviews)
"Delightful cottage, super convenient, and our host was extremely nice and attentive. "
United States
Mark M.
The price is AED 1,024
AED 2,043 total
includes taxes & fees
29 Apr - 30 Apr
The Cottage on Royal - Historic Leesburg Home

Hunters Retreat with High Speed Internet

Hunters Retreat with High Speed Internet
Middleburg
10.0 out of 10, Exceptional, (6 reviews)
"We had the best fall weekend and the property is amazing "
United States
Kelly T.
The price is AED 1,157
AED 2,914 total
includes taxes & fees
5 May - 6 May
Hunters Retreat with High Speed Internet

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
10.0 out of 10, Exceptional, (3 reviews)
"A wonderfully equipped home in a lovely location. Everything you could ever need was on hand. "
United States
alison m.
The price is AED 220
AED 1,026 total
includes taxes & fees
29 Apr - 30 Apr
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
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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