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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16

Vacation Homes in Upperville

Our top choices for Upperville vacation homes

Windy Knoll Adventure!
Property grounds

Windy Knoll Adventure!

8.8 out of 10, Excellent, (3)
"Great stay and very accommodating for outings/get together with friends. We loved the fire pit area. Great views of the Shenandoah river as well."
The price is ￥26,699
￥59,596 total
includes taxes & fees
Sep 16 - Sep 17
Windy Knoll Adventure!
Timeless Elegance in Restored Suite – King Bed & Private Spa Bath
1 bedroom, WiFi, bed sheets

Timeless Elegance in Restored Suite – King Bed & Private Spa Bath

10.0 out of 10, Exceptional, (1)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We loved Stone Gables! Our room (The Leesburg) was lovely, and we had gorgeous weather to relax in the pool. It was quite expensive, but it was definitely worth it to us."
The price is ￥47,902
￥94,414 total
includes taxes & fees
Aug 25 - Aug 26
Timeless Elegance in Restored Suite – King Bed & Private Spa Bath
This house is a 6 bedroom(s), 6.5 bathrooms, located in Upperville, VA.
Interior

This house is a 6 bedroom(s), 6.5 bathrooms, located in Upperville, VA.

The price is ￥161,446
￥270,793 total
includes taxes & fees
Sep 6 - Sep 7
This house is a 6 bedroom(s), 6.5 bathrooms, located in Upperville, VA.
Quaint Royal Cottage @ Historic Leesburg
Fridge, microwave, oven, stovetop

Quaint Royal Cottage @ Historic Leesburg

2.0 star property
10.0 out of 10, Exceptional, (8)
"Our stay was perfect for our family attending a Wedding in Leesburg. The Host was a great communicator and his guide about the area was wonderful."
The price is ￥26,052
￥63,248 total
includes taxes & fees
Aug 25 - Aug 26
Quaint Royal Cottage @ Historic Leesburg
Kalia’s Mountain Momma Getaway
Dining tables

Kalia’s Mountain Momma Getaway

10.0 out of 10, Exceptional, (11)
"Location was nice"
The price is ￥16,016
￥25,990 total
includes taxes & fees
Aug 25 - Aug 26
Kalia’s Mountain Momma Getaway
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Interior

Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street

10.0 out of 10, Exceptional, (3)
"Clean, cute, hot water, cool inside. I would stay again!!!"
The price is ￥24,245
￥38,547 total
includes taxes & fees
Sep 3 - Sep 4
Charming 1-bedroom apartment in Old Town Warrenton, walkable to Main Street
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Exterior

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

10.0 out of 10, Exceptional, (4)
"Great and quiet location with all the amenities. Getting to the parking is a bit tricky but other than that great place to stay with family"
The price is ￥13,965
￥46,956 total
includes taxes & fees
Sep 8 - Sep 9
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Red Cherry Oasis - Charming 2 bedroom villa with AC, WiFi in serene Aldie
Exterior

Red Cherry Oasis - Charming 2 bedroom villa with AC, WiFi in serene Aldie

The price is ￥14,415
￥41,058 total
includes taxes & fees
Sep 2 - Sep 3
Red Cherry Oasis - Charming 2 bedroom villa with AC, WiFi in serene Aldie
Newly renovated Farm cottage with Mountain views
Outdoor dining

Newly renovated Farm cottage with Mountain views

10.0 out of 10, Exceptional, (34)
"Everything was perfect! Clean, comfy, and peaceful. The pictures really do not do this property justice. Lots of neat details inside and out. The hostess is easy to get in touch with and truly cares about your stay! We plan to return. "
The price is ￥23,510
￥47,326 total
includes taxes & fees
Sep 1 - Sep 2
Newly renovated Farm cottage with Mountain views
Cameron Charmer pristine downtown apt with double master suites
Fridge, microwave, oven, stovetop

Cameron Charmer pristine downtown apt with double master suites

9.4 out of 10, Exceptional, (3)
"Nice house in a good central location. "
The price is ￥29,094
￥50,610 total
includes taxes & fees
Aug 25 - Aug 26
Cameron Charmer pristine downtown apt with double master suites
Lakefront House w/ Modern Comforts!
Property grounds

Lakefront House w/ Modern Comforts!

8.8 out of 10, Excellent, (3)
"The house is lovely. Very much enjoyed the stay. Looking forward to going back!!"
The price is ￥14,694
￥52,155 total
includes taxes & fees
Sep 1 - Sep 2
Lakefront House w/ Modern Comforts!
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
Terrace/patio

Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

10.0 out of 10, Exceptional, (15)
"The house is well maintained and furnished, and the outdoor space is lovely. We had a great weekend in Leesburg and would come again. "
The price is ￥23,143
￥55,511 total
includes taxes & fees
Aug 25 - Aug 26
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
1939 4BR Rustic Escape by Casino, 1939 4BR Rustic Escape by Casino
Terrace/patio

1939 4BR Rustic Escape by Casino, 1939 4BR Rustic Escape by Casino

10.0 out of 10, Exceptional, (2)
"Convenient location, close to casino & river tubing. The house was cozy & comfortable for all of us. "
The price is ￥18,221
￥43,787 total
includes taxes & fees
Aug 27 - Aug 28
1939 4BR Rustic Escape by Casino, 1939 4BR Rustic Escape by Casino
Mountain View Bungalow in Front Royal
Fridge, microwave, oven, stovetop

Mountain View Bungalow in Front Royal

"Excelente propiedad "
The price is ￥22,041
￥35,163 total
includes taxes & fees
Sep 5 - Sep 6
Mountain View Bungalow in Front Royal
Historic Hideaway
Fridge, microwave, oven, stovetop

Historic Hideaway

10.0 out of 10, Exceptional, (25)
"Perfect location, great indoor and outdoor vibes! "
The price is ￥19,837
￥45,457 total
includes taxes & fees
Aug 25 - Aug 26
Historic Hideaway
Welcome to the Ladybug Retreat!
Microwave, oven, stovetop, dishwasher

Welcome to the Ladybug Retreat!

10.0 out of 10, Exceptional, (1)
"This home is lovely and the host has thought of everything. We will definitely stay here again. "
The price is ￥25,715
￥59,483 total
includes taxes & fees
Sep 8 - Sep 9
Welcome to the Ladybug Retreat!
Spacious home steps from Main St and Shenandoah NP with firepit & large backyard
Fridge, microwave, oven, stovetop

Spacious home steps from Main St and Shenandoah NP with firepit & large backyard

10.0 out of 10, Exceptional, (14)
"We needed a place to stay for our golf foursome. Thisfour bedroom property met all of our needs."
Spacious home steps from Main St and Shenandoah NP with firepit & large backyard
Spacious Modern Home on Middleburg Horse Farm
Exterior

Spacious Modern Home on Middleburg Horse Farm

10.0 out of 10, Exceptional, (17)
"The house is very well designed and tastefully furnished. It is also the most thoughtfully equipped rental in which I've stayed. There was everything we needed to cook family meals and a fantastic coffee set up."
The price is ￥33,062
￥75,548 total
includes taxes & fees
Sep 7 - Sep 8
Spacious Modern Home on Middleburg Horse Farm
The River House
Fridge, microwave, oven, stovetop

The River House

10.0 out of 10, Exceptional, (5)
The price is ￥24,833
￥52,813 total
includes taxes & fees
Sep 1 - Sep 2
The River House
The Cottage on Royal - Historic Leesburg Home
Terrace/patio

The Cottage on Royal - Historic Leesburg Home

10.0 out of 10, Exceptional, (13)
"Thoroughly enjoyed our stay. The property was in a great location and was in excellent condition with all the amenities you needed to make your stay comfortable. I will definitely book this property again on my next visit!"
The price is ￥26,449
￥63,706 total
includes taxes & fees
Aug 25 - Aug 26
The Cottage on Royal - Historic Leesburg Home
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

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"Country Inn and Suites is just what we needed after a long day of driving. Check in was easy, the front desk was kind and helpful while the room was cool and comfortable. I will say that the property needs some updating. Waffle machine is broken, walls need paint in the hallways and rooms. We slept well and left rested. Thank you "
Lisabeth 1-night trip
Posted 11 hours ago
Country Inn & Suites by Radisson, Winchester, VA