Upperville Vacation Rentals
Change your mindBook hotels with free cancellation
Be pickySearch 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 homes
1. Mountain home w/ hot tub & sunroom
Mountain home w/ hot tub & sunroomFront Royal
9.0 out of 10, Wonderful, (32 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. "
Elissa S.
The price is CA $230
CA $431 total
includes taxes & fees
Sep 28 - Sep 29
2. 1910 Farmhouse on 6 Acres • VA Wine Country
1910 Farmhouse on 6 Acres • VA Wine CountryMarshall
9.6 out of 10, Exceptional, (5 reviews)
"We love this house. It was super quiet and cozy. The kitchen is the best stocked Vrbo kitchen we have ever encountered. If there is a drawback, I would say that it is the antique/original doorknobs. They do need to be repaired or replaced for ease of use. But on the other hand, no biggie and kind of add to the charm. We thoroughly enjoyed our stay!"
Mark H.
The price is CA $250
CA $549 total
includes taxes & fees
Sep 28 - Sep 29
3. Mountain Escape: Hottub + Fireplace + WiFi +PetsOK
Mountain Escape: Hottub + Fireplace + WiFi +PetsOKFront Royal
The price is CA $195
CA $579 total
includes taxes & fees
Oct 4 - Oct 5
4. DC Wine Country Farmhouse | 5 Peaceful Acres
DC Wine Country Farmhouse | 5 Peaceful AcresLoudoun County
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay. House is beautiful and clean and owner was highly responsive. "
Michele B.
The price is CA $313
CA $648 total
includes taxes & fees
Sep 22 - Sep 23
5. 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, trampolineHarpers Ferry
9.6 out of 10, Exceptional, (9 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. "
Maeve K.
The price is CA $152
CA $592 total
includes taxes & fees
Sep 23 - Sep 24
6. Spacious Modern Home on Middleburg Horse Farm
Spacious Modern Home on Middleburg Horse FarmMiddleburg
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!"
Denise B.
The price is CA $426
CA $865 total
includes taxes & fees
Oct 5 - Oct 6
7. Cozy Bear Chase Cottage
Cozy Bear Chase CottageMount Weather
10.0 out of 10, Exceptional, (46 reviews)
"Bear Chase is the ideal getaway from Alexandria, make the drive and stay the weekend or a week. Wonderful beer and other beverages, terrific food and entertainment. Amazing staff and the views and grounds are spectacular."
Scott F.
The price is CA $572
CA $1,194 total
includes taxes & fees
Sep 18 - Sep 19
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-BeachHarpers Ferry
9.8 out of 10, Exceptional, (10 reviews)
"Had a wonderful stay here. Shaun was an excellent host with easy communication. Peaceful location with a lake! Convenient to Harper’s Ferry. "
Liz P.
The price is CA $131
CA $443 total
includes taxes & fees
Sep 28 - Sep 29
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.
Find vacation rentals that suit your style
Apartments
Cabins
Save an average of 15% on thousands of hotels when you're signed in
Top Upperville Hotel Reviews
Quality Inn Winchester
10/10 Excellent
Find out more about Upperville
Upperville Vacation Homes information
Number of reviews | 331 |
|---|---|
Accommodation | 254 Vacation Homes |
Lowest Price | CA $310 |
Highest Price | CA $1,194 |
Explore a world of travel with Expedia
- B&B in Potomac Falls
- Apartments in Huntly
- Walk to Top
- B&B in Bristow
- Aldie Hotels
- Cabin Rentals in Paris
- Front Royal Hotels
- Hot Tub Mountain View Dog Friendly Modern Chalet
- Winchester Hotels
- Markham Hotels
- Middleburg Hotels
- Hampton Inn Front Royal
- Linden Hotels
- Paris Hotels
- Hunters Retreat with High Speed Internet
- Cabin Rentals in Elkwood
- Hotels near RdV Vineyards
- Hotels near Linden Vineyards
- Briar Patch Bed & Breakfast Inn
- Resorts in Airlie
- Motels in Fairfax
- Berryville Hotels
- Motels in Northern Virginia
- Vacation Homes in Casanova
- Farmstay in Woodville
- Buckskin Manor
- B&B in Boyce
- L'auberge Provencale Inn & Restaurant
- Apartments in Millwood
- Hotels near Bluemont Vineyard
- Relax Inn Motel
- Hotels near Washington Dulles Intl.
- Spacious Modern Home on Middleburg Horse Farm
- Motels in Casanova
- Cabin Rentals in Northern Virginia
- Aparthotels in Prince William County
- Motels in Warrenton
- Farmstay in Bristow
- Farmstay in Paeonian Springs
- Doubletree by Hilton Front Royal Blue Ridge Shadows
- Front Royal Hilltop Cabin w/ Panoramic Views!
- Apartments in Sterling
- Villas in Orlean
- Purcellville Hotels
- Pet-Friendly Hotels in Middleburg
- Motels in Winchester
- Resorts in Sterling
- Cabin Rentals in Fairfax
- Lodges in Riverton
- Beach Hotel Hotels in Blue Ridge
- Apartments in Winchester
- B&B in Manassas City County
- B&B in Midland
- Marshall Hotels
- Condo Rentals in Stephens City
- Villas in Fairfax
- Hyatt Hotels in Hamilton
- Breathtaking View with an Indoor Pool
- Marriott Hotels & Resorts in Linden
- Upperville Hotels
- Hotels near Stone Tower Winery
- Motels in Gore
- Flights from Edmonton (YEG) to Washington (DCA)
- Flights from Markham
- Flights from San Francisco (SFO) to Washington (IAD)
- Flights from Blue Ridge
- Flights from Calgary (YYC) to Washington (IAD)
- Flights from Saskatoon (YXE) to Washington (IAD)
- Flights from Toronto (YYZ) to Washington (DCA)
- Flights from Toronto (YYZ) to Winchester (WGO)
- Flights from Washington Dulles Intl.
- Flights from Ottawa (YOW) to Washington (DCA)
- Flights to Hamilton
- Flights from Toronto (YYZ) to Washington (IAD)
- Flights from Hamilton
- Flights from Calgary (YYC) to Washington (DCA)
- Flights to Gainesville
- Flights from Buffalo (BUF) to Washington (IAD)
- Flights from Montreal (YUL) to Washington (IAD)
- Flights from Regina (YQR) to Washington (IAD)
- Flights from Ronald Reagan Washington National
- Flights from Edmonton (YEG) to Washington (IAD)
- Flights from Vancouver (YVR) to Washington (IAD)
- Flights from Loudoun County
- Flights to Syria
- Porter Airlines Toronto (YTZ) to Washington (IAD) flights
- Flights to Boyce
- Flights from Winnipeg (YWG) to Washington (IAD)
- Flights to Washington Dulles Intl.
- Flights from Detroit (DTW) to Washington (IAD)
- Flights from Toronto (YTZ) to Washington (IAD)
- Flights from Ottawa (YOW) to Washington (IAD)
- Flights to Millwood