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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

Compare 201 Vacation Homes in Upperville with updated reviews, rates, and availability.

Trailside Retreat in breathtaking Western Loudoun
Outdoor dining

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (44)
"We had a full family 4 day retreat and Jill’s place was perfect. Lots of room, beds were so comfy and contained all the kitchen and bathroom supplies we needed. Everything was clean - they even had some toys for the kids. Great location…convenient to all activities, restaurants and hiking trails. We would definitely book again. 5 stars!"
Trailside Retreat in breathtaking Western Loudoun
Charles Town Home w/ Private Pool & Hot Tub
Pool

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (41)
"Our families decided to rent the property for a getaway close to the DMV. It was easy to check in, get around Charles Town and enjoy the property. Even with an unexpected 6" of snow, we still found time to appreciate everything the property had to offer."
Charles Town Home w/ Private Pool & Hot Tub
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
Fridge, microwave, oven, stovetop

Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly

10.0 out of 10, Exceptional, (33)
"Great house! Lots of room and cozy. Even saw some deer! Highly recommend!"
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
Cottage on King | Charming Historic Leesburg Home
Terrace/patio

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (48)
"Is there traffic/road noise? Yes. Can you walk to everything on King St? Also yes. Tradeoffs."
The price is AED 389
AED 853 total
includes taxes & fees
4 Mar - 5 Mar
Cottage on King | Charming Historic Leesburg Home
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun
Dining

Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun

10.0 out of 10, Exceptional, (23)
"Our group of seven was very, very comfortable there. It was nice to have two separate living areas one on the upper floor and one on the lower floor where one area could be the quieter area and the other area could be the louder area. Bedrooms were separate from the main living spaces on both the first floor and the basement which was very nice. Price per value was excellent, and whenever I return to the area, I will happily stay there again if it’s available!"
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun
Modern Mountain Retreat w/ Deck + Hot Tub!
Fridge, microwave, stovetop, dishwasher

Modern Mountain Retreat w/ Deck + Hot Tub!

10.0 out of 10, Exceptional, (66)
"The owner communicated well and was very responsive. The fireplace stove was great and we used the hot tub every day. Kitchen was well stocked. We cooked almost every meal and had everything we needed. The office space is a nice, private, comfortable space, as well. "
Modern Mountain Retreat w/ Deck + Hot Tub!
Gruner Bungalow at Otium Cellars
Smart TV, fireplace, table tennis, books

Gruner Bungalow at Otium Cellars

9.8 out of 10, Exceptional, (94)
"It's was great. We visited family in the area. And had our family Christmas together at this place. We played ping pong and pool when we where there. Great location for dogs. Plenty of space to run and play. The house was great as well. Plenty of space for everyone."
Gruner Bungalow at Otium Cellars
Rural Home, Hot Tub, Campfire, Hardwood Floors
Snow and ski sports

Rural Home, Hot Tub, Campfire, Hardwood Floors

9.4 out of 10, Exceptional, (71)
"Lovely house. A couple of rooms were cold but not unbearably cold. The large table in the sun room was awesome for Thanksgiving dinner. We would definitely stay again if we wanted a house in the area."
Rural Home, Hot Tub, Campfire, Hardwood Floors
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
Terrace/patio

5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine

9.8 out of 10, Exceptional, (47)
"With grandparents and 2 families with children, not only was the house perfect but the fenced yard was huge and spectacular. We didn’t use the hot tub, but there was plenty of good space for adults, too. We gathered for a family wedding, but the space enabled us to spend a few wonderful relaxing days with family we rarely see. Communication with Leora was prompt and accommodating. 5 stars all around! Thank you!"
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area
Outdoor dining

Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area

9.8 out of 10, Exceptional, (52)
"Thank you"
Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area
The PINK PEARL in Historic Leesburg
Outdoor dining

The PINK PEARL in Historic Leesburg

9.6 out of 10, Exceptional, (31)
"Loved the location and ability to sleep 8 people. Great for a weekend stay!"
The PINK PEARL in Historic Leesburg
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
Property grounds

#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries

10.0 out of 10, Exceptional, (5)
"Wonderful hosts and a great home! Lots of extra special touches."
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
New - Modern Mountain Retreat w/ Hot tub and view!
Fridge, microwave, oven, stovetop

New - Modern Mountain Retreat w/ Hot tub and view!

10.0 out of 10, Exceptional, (13)
"This house is beautiful and so thoughtfully decorated and stocked with everything you’d need for the perfect weekend. Highly recommend for anyone looking for a relaxing retreat to disconnect and reconnect with family and friends."
New - Modern Mountain Retreat w/ Hot tub and view!
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
Fridge, microwave, oven, stovetop

YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

10.0 out of 10, Exceptional, (97)
"Plenty of snow on the ground prior to the inauguration, and a perfect Winter setting for our family to enjoy their old stomping ground and see friends and colleagues. Lovely home and we will stay again!"
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
Cozy Country Getaway in the Heart of Upperville
Smart TV

Cozy Country Getaway in the Heart of Upperville

10.0 out of 10, Exceptional, (7)
"Highly recommend this place."
Cozy Country Getaway in the Heart of Upperville
Terra Alta - Incredible River Views and Hot Tub!
Outdoor spa tub

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (54)
"Multiple generations enjoyed this lovely house with plenty of space, well stocked kitchen, and great location for winery visits. Highlights include extra sleeping space, local coffee provided by the host, and the hottub! Gorgeous views and responsive hosy! "
The price is AED 367
AED 1,468 total
includes taxes & fees
6 Mar - 7 Mar
Terra Alta - Incredible River Views and Hot Tub!
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!
Fridge, microwave, oven, stovetop

Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!

10.0 out of 10, Exceptional, (10)
"First time using a rental service and Karen and Todd made it super easy. They were communicative before, during, and even after our stay. The house easily accommodated the 8 people in my party. "
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!
Modern Country House on the Shenandoah River
Property grounds

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (31)
"This was a perfect long weekend stay for two families (4 adults, 4 kids). Comfortable, spacious, and well-equipped house on a beautiful property. Very responsive and helpful host. Would give 6 stars if I could. We hope to be back soon!"
Modern Country House on the Shenandoah River
Walk to Top-Rated Restaurants & Trails! 7BR w/HotTub Gazebo & Built-in FirePit!
Outdoor dining

Walk to Top-Rated Restaurants & Trails! 7BR w/HotTub Gazebo & Built-in FirePit!

10.0 out of 10, Exceptional, (12)
"Good location. Excellent amenities. Inside and outside! Exactly as advertised. The large farmhouse dining table was perfect for everyone to enjoy meals & play card games together! A Great place for our Family gathering to start the New Year!! "
Walk to Top-Rated Restaurants & Trails! 7BR w/HotTub Gazebo & Built-in FirePit!
The Lodge at Stoneleigh
Interior

The Lodge at Stoneleigh

10.0 out of 10, Exceptional, (7)
"Great house; perfect for family with lots of activities in the area as well."
The Lodge at Stoneleigh
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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Other property types in Upperville

Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
Smart TV, DVD player, books, video library

Cozy Mountain Cabin w/ Steam Shower! Great for Couples.

10.0 out of 10, Exceptional, (58)
"To start this cabin was AMAZINGLY Clean. Everything was just as host said it would be, the communication was outstanding, check in was perfect and seamless and the only note to self gfor next trip is pay close attention to the "Drive In" instructions. Can be a little challenging especially at night. Wonderful Place and people!!"
The price is AED 551
AED 1,231 total
includes taxes & fees
17 Mar - 18 Mar
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
Exterior

Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

9.6 out of 10, Exceptional, (50)
"My husband and I along with our 2 small dogs had a wonderful stay at this lovely mountain retreat. The cabin was clean and comfortable and had everything that we needed to cook breakfast and an easy dinner each evening. The property was beautiful with lots of tall old growth trees that were beautiful with the fall colors and even though it was in a community you felt like you were in a secluded mountain retreat because most of the homes were obsured by the trees; and it is on a dead end road...
The price is AED 896
AED 1,043 total
includes taxes & fees
13 Mar - 14 Mar
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
18th Century Stone Cottage minutes from historic Middleburg
Exterior

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (37)
"The cottage is perfect for a couple. Small, cozy, plenty of room. The heating system takes some learning, but the fireplace is easy. The grounds are beautiful and if the weather cooperates, take the time to walk around them.Proximity to Middleburg and Upperville makes it even better.I hope to return."
The price is AED 1,010
AED 1,446 total
includes taxes & fees
11 Mar - 12 Mar
18th Century Stone Cottage minutes from historic Middleburg
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.