Search Vacation Homes in Upperville

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
21 Rab. I - 23 Rab. I
In two weeks
28 Rab. I - 30 Rab. I
In one month
11 Rab. II - 13 Rab. II
In two months
9 Jum. I - 11 Jum. I

Compare 214 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
1805 Farmhouse with Heated Pool in Harpers Ferry
Exterior

1805 Farmhouse with Heated Pool in Harpers Ferry

10.0 out of 10, Exceptional, (37)
"The house and property were absolutely perfect for our group. Lots of privacy, the renovations are very well done. All technology is top of the line and works as expected. The pool, or in our case hot tub, was even better than we expected. It was used both nights we were there. The barn apartment is a wonderful place for some additional privacy from a large group, and is extremely comfortable. We would recommend this house 100%. "
1805 Farmhouse with Heated Pool in Harpers Ferry
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
Historic Hideaway
Fridge, microwave, oven, stovetop

Historic Hideaway

10.0 out of 10, Exceptional, (15)
"This property was very clean and had everything we needed. Also in a great location to the heart of Leesburg, but on a quiet street. Would definitely stay here again."
The price is SAR 563
SAR 1,229 total
includes taxes & fees
19 Mar - 20 Mar
Historic Hideaway
Modern Home on Middleburg Equestrian Farm
Fridge, microwave, oven, stovetop

Modern Home on Middleburg Equestrian Farm

10.0 out of 10, Exceptional, (11)
"We had a lovely girls weekend away in this modern home tucked away in Middleburg. It was conveniently located near town and among rolling roads of horse country. The house was cosy, comfortable and had all the amenities of home. We especially liked the comf beds and Nespresso machine. "
Modern Home on Middleburg Equestrian Farm
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, (9)
"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 SAR 686
SAR 1,540 total
includes taxes & fees
16 Mar - 17 Mar
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
#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, (6)
"Stayed with my three daughters for a Galentine’s weekend and had a great time! Enjoyed some of the nearby hiking trails and soaked up the quiet beauty of the area."
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries
Gruner Bungalow at Otium Cellars
Smart TV, fireplace, table tennis, books

Gruner Bungalow at Otium Cellars

9.8 out of 10, Exceptional, (95)
"Spacious, lovely, home that was perfect for 50th bday celebration with 8 women!"
Gruner Bungalow at Otium Cellars
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
Indulge in Elegance: 7 BR Manor with Events in Historic Waterford
Desk, iron/ironing board, WiFi, bed sheets

Indulge in Elegance: 7 BR Manor with Events in Historic Waterford

Indulge in Elegance: 7 BR Manor with Events in Historic Waterford
Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia
Property grounds

Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia

10.0 out of 10, Exceptional, (54)
"The property is quite lovely, surrounded by the rolling hills of western Virginia. The house was perfect, a lot of space to spread out if needed. We spent our evenings on the screened in back porch. The pool and gardens were an added bonus. Every evening the neighbor cows would graze along the fence line- just a lovely get away from the City! "
Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia
Hot tub, Campfire ring and great location!
Snow and ski sports

Hot tub, Campfire ring and great location!

9.4 out of 10, Exceptional, (117)
"Clean and nice place"
Hot tub, Campfire ring and great location!
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
Terrace/patio

Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

9.8 out of 10, Exceptional, (27)
"Fantastic weekend with my family...highly recommend 3 Penny Acres!"
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
Mountain Getaway - 7 beds (2 King) - Large Common Area
Terrace/patio

Mountain Getaway - 7 beds (2 King) - Large Common Area

10.0 out of 10, Exceptional, (10)
"This place was everything and more. We had quite a large group coming in for a weekend trip, and this place was able to fit all of us. The pictures do not do it justice because this place was beautiful, clean, and spacious. Would love to come back one day!"
Mountain Getaway - 7 beds (2 King) - Large Common Area
This house is a 2 bedroom(s), 2 bathrooms, located in Winchester, VA.
Exterior

This house is a 2 bedroom(s), 2 bathrooms, located in Winchester, VA.

9.4 out of 10, Exceptional, (6)
"This cabin was much larger than expected. It was clean and comfortable with two big bedrooms and two full (big!) bathrooms. Easy access to Winchester and cute cows!"
This house is a 2 bedroom(s), 2 bathrooms, located in Winchester, VA.
Breathtaking views with an indoor private pool, come escape with us
Exterior

Breathtaking views with an indoor private pool, come escape with us

9.8 out of 10, Exceptional, (246)
"We have been coming for six years now and I expect we will come for 20 more. Love this house."
Breathtaking views with an indoor private pool, come escape with us
Buckskin Manor - Historic, Pool, 66 Acre Vineyard
Property grounds

Buckskin Manor - Historic, Pool, 66 Acre Vineyard

9.6 out of 10, Exceptional, (17)
"We had a fantastic stay at the property. The home is very charming and the pool is great. The location was also really nice. Close to wineries and hiking. Two points of feedback are that the dishes were visibly dirty upon arrival and all of the mattresses need to be replaced. Everyone in the group slept poorly and noted that the mattresses were uncomfortable. The master bedroom should likely also have a larger bed."
The price is SAR 1,264
SAR 4,234 total
includes taxes & fees
6 Apr - 7 Apr
Buckskin Manor - Historic, Pool, 66 Acre Vineyard
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!
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
Spacious estate in charming Purcellville with WiFi, fitness room, AC
Fridge, microwave, oven, stovetop

Spacious estate in charming Purcellville with WiFi, fitness room, AC

2.0 star property
10.0 out of 10, Exceptional, (3)
"Beautiful countryside, great selection of local wineries and accessible to West Virginia, this property is hard to beat."
Spacious estate in charming Purcellville with WiFi, fitness room, AC
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.
Don't see what you're looking for?
See all available properties in Upperville
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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, (59)
"Fabulous steam shower, high quality linens and very comfy bed. Fred likes a firm mattress and I like soft and we were both happy and slept well in the Master. Lovely assortment of coffees and teas. And one of my favorites an electric tea kettle. . Very quiet. Beautiful sun room for dining or working or relaxing. Plenty of pillows and blankets. Bathroom well supplied. We ate in most of the time and appliances. Definitely recommend!ekettle. "
The price is SAR 563
SAR 1,253 total
includes taxes & fees
17 Mar - 18 Mar
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Outdoor dining

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (81)
"Overall rating & experience 4.5/5 Stars. Great owners who communicated very well and timely.This precious cabin is tucked in the Shenandoah mountains & is very quiet, clean and such a lovely place located by great local wineries and eateries with beautiful scenery & mountain views, The wood-burning stove was an added bonus. We all are very happy with our experience and time here(3 nights). This cabin is also very well furnished, new, very clean, and has all the necessities.We highly recommend it...
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
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 SAR 969
SAR 1,121 total
includes taxes & fees
8 Apr - 9 Apr
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
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.