Upperville Vacation Rentals
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Our top choices for Upperville vacation homes
1. 1910 Farmhouse on 6 Acres • VA Wine Country
1910 Farmhouse on 6 Acres • VA Wine CountryMarshall
9.6 out of 10, Exceptional, (5 reviews)
"If we managed to do everything, sing, dance, play, we loved the comfortable place for us"
Erick U.
The price is CA $227
CA $505 total
includes taxes & fees
Dec 14 - Dec 15
2. super cosy cottage with high speed internet!
super cosy cottage with high speed internet!Middleburg
9.6 out of 10, Exceptional, (19 reviews)
"The area was surrounded by horses, Horse farms all around, which was lovely. Very quite and peaceful. Enjoyed my time there."
Lynette
The price is CA $241
CA $431 total
includes taxes & fees
Nov 17 - Nov 18
3. Spacious Modern Home on Middleburg Horse Farm
Spacious Modern Home on Middleburg Horse FarmMiddleburg
10.0 out of 10, Exceptional, (23 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 $449
CA $820 total
includes taxes & fees
Nov 16 - Nov 17
4. Mountain Escape | Hot Tub, Fire Pit + Fireplace, Pet Friendly | 3BR, Sleeps 6
Mountain Escape | Hot Tub, Fire Pit + Fireplace, Pet Friendly | 3BR, Sleeps 6Front Royal
The price is CA $205
CA $554 total
includes taxes & fees
Nov 15 - Nov 16
5. Mountain Views w/Hot Tub, 95” TV & Trail Access
Mountain Views w/Hot Tub, 95” TV & Trail AccessShenandoah Farms
9.0 out of 10, Wonderful, (2 reviews)
"Just as described."
Matt F.
The price is CA $348
CA $663 total
includes taxes & fees
Nov 18 - Nov 19
6. Hunters Retreat with High Speed Internet
Hunters Retreat with High Speed InternetMiddleburg
10.0 out of 10, Exceptional, (6 reviews)
"We had the best fall weekend and the property is amazing "
Kelly T.
The price is CA $578
CA $1,241 total
includes taxes & fees
Nov 17 - Nov 18
7. Cozy 3BR Retreat | Perfect for Families & Groups
Cozy 3BR Retreat | Perfect for Families & GroupsApple Mountain Lake
The price is CA $233
CA $445 total
includes taxes & fees
Nov 18 - Nov 19
8. Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6Front Royal
9.4 out of 10, Exceptional, (3 reviews)
"The gravel road to get to the properly is an adventure. The owner described it perfectly."
Denise A.
The price is CA $192
CA $555 total
includes taxes & fees
Nov 15 - Nov 16
9. Mountain View Bungalow in Front Royal
Mountain View Bungalow in Front RoyalFront Royal
10.0 out of 10, Exceptional, (51 reviews)
"It was great and beautiful place to staying. Thanks for hospitality"
Onon
The price is CA $193
CA $307 total
includes taxes & fees
Nov 22 - Nov 23
10. Historic 6BR • EventsandConcierge! • Pool • Wineries
Historic 6BR • EventsandConcierge! • Pool • WineriesHume
The price is CA $518
CA $1,754 total
includes taxes & fees
Nov 16 - Nov 17
11. Pool Table, Fireplace & Deck near Shenandoah Park
Pool Table, Fireplace & Deck near Shenandoah ParkFront Royal
10.0 out of 10, Exceptional, (2 reviews)
"Great location. Very quiet neighborhood good for walking"
tom c.
The price is CA $306
CA $701 total
includes taxes & fees
Nov 23 - Nov 24
12. Mountain Lake Retreat: Hot Tub, Fire Pit, Fenced Yard, Pets, Beach, Winery
Mountain Lake Retreat: Hot Tub, Fire Pit, Fenced Yard, Pets, Beach, WineryHarpers Ferry
9.8 out of 10, Exceptional, (16 reviews)
"We had a lovely stay and it was so nice for our dog as well. The Mountain Lake Cub had a doggy beach day on Saturday morning and it was a super fun experience. The host was friendly and responsive!"
Dawn S.
The price is CA $155
CA $484 total
includes taxes & fees
Nov 22 - Nov 23
13. Still Meadow Farm
Still Meadow FarmPurcellville
10.0 out of 10, Exceptional, (2 reviews)
"Still Meadow is a beautiful place to stay, super clean, We would definitely recommend. Host was responsive and accommodating."
Jodie J.
The price is CA $1,049
CA $1,799 total
includes taxes & fees
Nov 23 - Nov 24
14. Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge
Iconic Chalet: Sauna • Hot Tub • Fire Pit • PlungeShannondale
10.0 out of 10, Exceptional, (4 reviews)
"My family and ai had an amazing stay at Deb and Alex’s rental in WV! It was easy to check-in, very clean, and had convenient amenities! Would definitely consider staying with them again!"
Anonymous traveller
The price is CA $323
CA $656 total
includes taxes & fees
Dec 7 - Dec 8
15. Stone Cabin on Valley View: Fire Pit + Hot Tub
Stone Cabin on Valley View: Fire Pit + Hot TubHarpers Ferry
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful scenery! Beautiful home! Wonderful hosts!"
Brian S.
The price is CA $220
CA $504 total
includes taxes & fees
Dec 1 - Dec 2
16. LUX Lakefront King Suites w/Dock, HotTub, Kayaks
LUX Lakefront King Suites w/Dock, HotTub, KayaksShannondale
10.0 out of 10, Exceptional, (4 reviews)
"Amazing house and host! This is the perfect layout as each bedroom has a large bed and it's own bathroom. Beautiful views if the lake and mountain. "
Tom V.
The price is CA $1,839
CA $2,006 total
includes taxes & fees
Nov 17 - Nov 18
17. Leesburg Hideaway- King Bed + Private Backyard
Leesburg Hideaway- King Bed + Private BackyardLeesburg
10.0 out of 10, Exceptional, (40 reviews)
"Clean sweet place to stay and relax. Couldn't have been nicer."
Avis V.
The price is CA $202
CA $430 total
includes taxes & fees
Nov 19 - Nov 20
18. NEW! Greek Spa - Frisbee Golf - Stonefire Pizza
NEW! Greek Spa - Frisbee Golf - Stonefire PizzaFront Royal
The price is CA $111
CA $392 total
includes taxes & fees
Nov 17 - Nov 18
19. 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, (10 reviews)
"Welcoming host, great place!"
Amanda M.
The price is CA $148
CA $457 total
includes taxes & fees
Dec 1 - Dec 2
20. Chalet in Harpers Ferry
Chalet in Harpers FerryHarpers Ferry
10.0 out of 10, Exceptional, (3 reviews)
"Great time. In the mountains. Clean. Ease of communication. Would stay again"
Courtney C.
The price is CA $463
CA $773 total
includes taxes & fees
Nov 17 - Nov 18
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
The George Washington Hotel, A Wyndham Grand Hotel
10/10 Excellent
Find out more about Upperville
Upperville Vacation Homes information
Number of reviews | 205 |
|---|---|
Accommodation | 253 Vacation Homes |
Lowest Price | CA $307 |
Highest Price | CA $2,006 |
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