Upperville Vacation Rentals

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Check prices for these dates

Tonight
Oct 24 - Oct 25
Tomorrow
Oct 25 - Oct 26
This weekend
Oct 24 - Oct 26
Next weekend
Oct 31 - Nov 2

Vacation Rentals in Upperville

Dining
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
10.0 out of 10, Exceptional, (76)
"Wonderful view from the sunroom. Peaceful and rejuvenating stay in this welcoming home. "
United States
Michelle M.
The price is ￥16,068
￥42,683 total
includes taxes & fees
Oct 29 - Oct 30
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Property grounds
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
10.0 out of 10, Exceptional, (47)
"Beautiful area"
United States
Richard S.
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
1 bedroom, iron/ironing board, free WiFi, bed sheets
Silo Tiny House Cabin
Silo Tiny House Cabin
9.6 out of 10, Exceptional, (7)
"Heated mattress was the best. Thank you! "
United States
Glenn M.
The price is ￥26,660
￥45,059 total
includes taxes & fees
Nov 5 - Nov 6
Silo Tiny House Cabin
Exterior
18th Century Stone Cottage minutes from historic Middleburg
18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (49)
"What a peaceful place and wonderful views."
United States
Debbie M.
The price is ￥41,962
￥60,090 total
includes taxes & fees
Oct 29 - Oct 30
18th Century Stone Cottage minutes from historic Middleburg
Property grounds
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
9.4 out of 10, Exceptional, (16)
"Four family members stayed for a four day weekend. The place was spotless when we arrived and all amenities are as described. The location is perfect for visiting Harpers Ferry, Shepherdstown, and Antietam. We had wonderful time."
United States
David B.
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Outdoor dining
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
10.0 out of 10, Exceptional, (96)
"Very nice relaxing getaway, quite how do you spell quiet and serene location. "
United States
Dan C.
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Exterior
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
9.2 out of 10, Wonderful, (61)
"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"
United States
Chelsey-Ann
The price is ￥26,001
￥45,371 total
includes taxes & fees
Nov 11 - Nov 12
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
3 bedrooms, free WiFi, bed sheets
Lakefront Log Cabin w/ Dreamy Waterfront Patio!
Lakefront Log Cabin w/ Dreamy Waterfront Patio!
2.0 star property
9.6 out of 10, Exceptional, (9)
"We loved the location and the property itself was decorated very cute. Would be awesome to have kayaks or something to take on the water but that is the only thing I would change! "
United States
Jessica K.
The price is ￥15,259
￥49,934 total
includes taxes & fees
Oct 27 - Oct 28
Lakefront Log Cabin w/ Dreamy Waterfront Patio!
Outdoor dining
Breathtaking View with an Indoor Pool
Breathtaking View with an Indoor Pool
9.8 out of 10, Exceptional, (260)
"Great Property"
United States
Scott B.
Breathtaking View with an Indoor Pool
Terrace/patio
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
10.0 out of 10, Exceptional, (17)
"Great location! Host very responsive and accommodating. Private yard. House is well maintained. Will stay again if the availability is there. "
United States
Melinda R.
The price is ￥24,170
￥57,625 total
includes taxes & fees
Nov 2 - Nov 3
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
Outdoor dining
Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people
Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people
8.4 out of 10, Very Good, (25)
"This house"
United States
Alana D.
Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people
Smart TV, fireplace, stereo
Escape to Shenandoah River, Hot Tub after a Hike!
Escape to Shenandoah River, Hot Tub after a Hike!
10.0 out of 10, Exceptional, (51)
"Very nice updated home in a beautiful peaceful setting. I would highly recomend it!"
United States
Kathy L.
The price is ￥27,199
￥62,820 total
includes taxes & fees
Nov 11 - Nov 12
Escape to Shenandoah River, Hot Tub after a Hike!
Fridge, microwave, oven, stovetop
Single Level, 3 Bedroom Home In Between Harper's Ferry & Casino.
Single Level, 3 Bedroom Home In Between Harper's Ferry & Casino.
7.6 out of 10, Good, (26)
"Easy check in. House is located in a cluster of homes. Photos are misleading. Cleanliness was sub par. Linens and towels from previous guests were laying on top of the washer. Wasn’t sure if the linens and towels that we did have were even clean and fresh. Home smelled of alcohol and cigarettes. Good location."
United States
Anonymous traveler
Single Level, 3 Bedroom Home In Between Harper's Ferry & Casino.
Fridge, microwave, oven, stovetop
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
9.4 out of 10, Exceptional, (27)
"The house was very clean upon arrival. We enjoyed spending time in the hot tub and playing pool on a kid’s pool table. It was close the Harper’s Ferry. We also saw deer very close both days we were there, and we loved this!!"
United States
Kelly
The price is ￥34,562
￥57,652 total
includes taxes & fees
Nov 11 - Nov 12
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Smart TV, fireplace, table tennis, books
Gruner Bungalow at Otium Cellars
Gruner Bungalow at Otium Cellars
9.8 out of 10, Exceptional, (102)
"The house is beautiful; very updated with lots of places to sit and have conversations! It is really close to the tasting room at Otium, but it was never an issue. The pool is really nice, too! Our group of families had a great time! Overall, beautiful house and we had an amazing time."
United States
Jenna C.
Gruner Bungalow at Otium Cellars
Fridge, microwave, oven, stovetop
The River House
The River House
10.0 out of 10, Exceptional, (9)
"Host communicated well. Great location right on the river. Family had a great time. "
United States
Geoff C.
The price is ￥13,184
￥38,947 total
includes taxes & fees
Nov 3 - Nov 4
The River House
Terrace/patio
The Apple Mountain House
The Apple Mountain House
9.8 out of 10, Exceptional, (6)
"Amazing place to relax."
United States
Edna K.
The price is ￥20,304
￥59,590 total
includes taxes & fees
Nov 5 - Nov 6
The Apple Mountain House
Outdoor dining
A peaceful, forest retreat with stunning views near historic Harpers Ferry.
A peaceful, forest retreat with stunning views near historic Harpers Ferry.
9.4 out of 10, Exceptional, (3)
"Great place to stay!! Very happy with the accommodations "
United States
Amanda E.
The price is ￥27,344
￥58,334 total
includes taxes & fees
Nov 5 - Nov 6
A peaceful, forest retreat with stunning views near historic Harpers Ferry.
Property grounds
Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area
Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area
9.8 out of 10, Exceptional, (61)
"The house was as advertised. We traveled with 4 other couples and never felt crowded. it was also very close to Quattro Goombas our favorite brewery/winery. Beautiful home and property made for a 5 star stay from all 5 couples."
United States
Jim K.
Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area
Exterior
Blue Ridge Getaway - Sunset Views, A.T. Access
Blue Ridge Getaway - Sunset Views, A.T. Access
10.0 out of 10, Exceptional, (60)
"Great stay, great views. Clean property. Would highly recommend!"
United States
Ryan N.
The price is ￥15,259
￥56,355 total
includes taxes & fees
Nov 12 - Nov 13
Blue Ridge Getaway - Sunset Views, A.T. Access
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

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"Clean room. Good breakfast"
RAY 1-night trip
Posted 3 days ago
Travelodge by Wyndham Winchester

Find out more about Upperville

Search for holiday rentals in Upperville on Expedia! You can easily find your home rentals, villas, holiday apartments in Upperville using one of the methods below:

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Frequently asked questions

Can I find a vacation rental in Upperville?

Yes, we offer vacation rentals close to well known attractions in Upperville, or you can go with a more secluded option if you're looking for relaxation. Upperville is known for its restaurants.

What are some of the best vacation home rentals that Upperville has to offer?

Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!: This vacation home rental outside of Upperville offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the hot tub in this rental home to help you unwind.

How many vacation rentals are there in Upperville?

Choose from 5 Expedia vacation rentals in Upperville for a memorable vacation.

What can I see and do in Upperville?

While exploring the area, visit family-friendly sights like Great Country Farms, or get outside and enjoy nature at Upperville Park. Sky Meadows State Park and Delaplane Cellars are a couple of places you'll find in the larger area.

What are vacation rentals like in Upperville?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Upperville. Vacation rentals offer extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a family trip or a small group gathering.