Upperville Holiday Rentals

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Check prices for these dates

In two weeks
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Holiday Rentals in Upperville

Outdoor spa tub
Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!

Charles Town
9.6 out of 10, Exceptional, (65)
"I recommend this house for the Harpers Ferry location. Four spacious bedrooms, three bathrooms, hot tub, and games."
United States
joshua s.
The price is HK$777
HK$3,147 total
includes taxes & fees
4 Dec - 5 Dec
Terra Alta - Incredible River Views and Hot Tub!
Property grounds
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

Front Royal
10.0 out of 10, Exceptional, (49)
"My wife and wanted a short and sweet trip for the weekend and this was the perfect place. Loved the views. Sunrise from the wall of windows was beautiful. Place was beautiful."
United States
Michael R.
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
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!

Leesburg
10.0 out of 10, Exceptional, (19)
"The location of the house was perfect for our needs. We enjoyed their hot tub and fire pit. The king size bed, sheets and comforter were very comfortable. We only stayed 3 nights and it was a fair price for 4 adults and 2 kids. "
United States
Donna G.
The price is HK$1,231
HK$2,926 total
includes taxes & fees
18 Nov - 19 Nov
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
Outdoor dining
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

Linden
10.0 out of 10, Exceptional, (99)
"We enjoyed our weekend at Whiskey Hill Cabin. The cabin was beautiful and very clean. We were looking for quiet and found it there. Beautiful view and scenic drive to get there!"
United States
Heather G.
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Terrace/patio
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River

Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River

Front Royal
9.2 out of 10, Wonderful, (242)
"The tranquility and peacefulness was just what we were looking for. We have already inquired about the other cabins and dates available. We will definitely book again! We hated to leave! 10 out of 10 stars!"
United States
Rebecca M.
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
3 bedrooms, free WiFi, bed sheets
Lakefront Log Cabin w/ Dreamy Waterfront Patio!

Lakefront Log Cabin w/ Dreamy Waterfront Patio!

2.0 star property
Harpers Ferry
9.8 out of 10, Exceptional, (11)
"Exactly what we expected from the listing. Nice, clean, well appointed cabin on the lake with comfortable beds. Easy check-in and check-out procedures and good communication with management. "
United States
Kimberly J.
The price is HK$777
HK$2,568 total
includes taxes & fees
1 Dec - 2 Dec
Lakefront Log Cabin w/ Dreamy Waterfront Patio!
Smart TV, fireplace, ping pong, books
Gruner Bungalow at Otium Cellars

Gruner Bungalow at Otium Cellars

Purcellville
9.8 out of 10, Exceptional, (102)
"Beautiful home with a great pool just steps away from a great winery"
United States
Dane W.
Gruner Bungalow at Otium Cellars
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

Harpers Ferry
8.2 out of 10, Very good, (29)
"We had a great time "
United States
Robert M.
Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people
Exterior
Blue Ridge Getaway - Sunset Views, A.T. Access

Blue Ridge Getaway - Sunset Views, A.T. Access

Harpers Ferry
10.0 out of 10, Exceptional, (61)
"The house and property were very nice. Everything was as described. We enjoyed our stay."
United States
Sara S.
The price is HK$777
HK$2,870 total
includes taxes & fees
20 Nov - 21 Nov
Blue Ridge Getaway - Sunset Views, A.T. Access
Exterior
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

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

Harpers Ferry
9.2 out of 10, Wonderful, (61)
"We had a get-together with our bridal party folks from out of town, and this was a great place to relax and play games. Cute decor, nice amenities. "
United States
Ashley Lynn C.
The price is HK$1,170
HK$2,124 total
includes taxes & fees
18 Nov - 19 Nov
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
Fridge, microwave, oven, stovetop
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Harpers Ferry
9.8 out of 10, Exceptional, (105)
"So close to River Riders Adventures and the National Historic Park."
United States
Philip B.
The price is HK$1,357
HK$4,415 total
includes taxes & fees
24 Nov - 25 Nov
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Property grounds
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Harpers Ferry
9.6 out of 10, Exceptional, (101)
"Great find for a girls trip…house is close to lots of different activities and very easy to get to. Perfect place to a weekend getaway!"
United States
Jennifer L.
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
1 bedroom, iron/ironing board, free WiFi, bed sheets
Wild And Wonderful Silos

Wild And Wonderful Silos

Harpers Ferry
9.6 out of 10, Exceptional, (8)
"Very nice place. Staying in a silo was a unique experience. It snowed while we were there and it was beautiful. We would definitely stay again. There is a lot to see and do in Harper's Ferry and the surrounding area."
United States
Teresa B.
The price is HK$1,364
HK$2,330 total
includes taxes & fees
18 Nov - 19 Nov
Wild And Wonderful Silos
Fridge, microwave, oven, stovetop
The River House

The River House

Charles Town
10.0 out of 10, Exceptional, (9)
"Excellent experience. Super clean house. Excellent location right on the river! Would definitely rent again!!"
United States
Casey W.
The price is HK$1,028
HK$2,449 total
includes taxes & fees
17 Nov - 18 Nov
The River House
Fridge, microwave, oven, stovetop
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Harpers Ferry
9.4 out of 10, Exceptional, (27)
"We had a great stay and the house was perfect for a quick getaway weekend for our family. Close to wineries and explored Harper’s Ferry. Communication with the host Tony was great. We would stay here again!"
United States
Samantha W.
The price is HK$1,521
HK$2,629 total
includes taxes & fees
17 Nov - 18 Nov
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Outdoor dining
Breathtaking View with an Indoor Pool

Breathtaking View with an Indoor Pool

bluemont
9.8 out of 10, Exceptional, (262)
"Love it here!"
United States
Brent C.
Breathtaking View with an Indoor Pool
Property grounds
The Vue - Mountain top hot tub overlooking the Shenandoah River

The Vue - Mountain top hot tub overlooking the Shenandoah River

2.0 star property
Front Royal
9.8 out of 10, Exceptional, (8)
"Love the view and beautiful appointed decor throughout the home…"
United States
Lynn M.
The price is HK$1,462
HK$3,266 total
includes taxes & fees
23 Nov - 24 Nov
The Vue - Mountain top hot tub overlooking the Shenandoah River
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

Harpers Ferry
9.4 out of 10, Exceptional, (19)
"We had a great stay for the long Memorial Day Weekend. A very comfortable property with everything you could need for just you or a small group. Easy access to Harpers Ferry, hikes, breweries, wineries, and more. Most places are about a 20 minute drive—a bit longer for a full grocery store so recommend stocking up before you arrive. Very communicative and helpful host. Highly recommend!"
United States
Christian H.
The price is HK$1,290
HK$3,371 total
includes taxes & fees
17 Nov - 18 Nov
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Property grounds
Apple Mountain Retreat

Apple Mountain Retreat

Linden
10.0 out of 10, Exceptional, (21)
"My groomsmen and i were able to chsnge, take pictures and watch football. Perfect place, very clean and has everything you could ask for."
United States
Dan K.
The price is HK$1,049
HK$1,817 total
includes taxes & fees
16 Nov - 17 Nov
Apple Mountain Retreat
Smart TV, fireplace, stereo
Escape to Shenandoah River, Hot Tub after a Hike!

Escape to Shenandoah River, Hot Tub after a Hike!

Front Royal
10.0 out of 10, Exceptional, (52)
"Cabin was clean...private area...wpuld recommend "
United States
Brent E.
The price is HK$877
HK$2,578 total
includes taxes & fees
17 Nov - 18 Nov
Escape to Shenandoah River, Hot Tub after a Hike!
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

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Nice room, helpful and courteous staff"
Michael 1-night trip
Posted 2 days ago
The George Washington Hotel, A Wyndham Grand Hotel

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:

  • View our selection of featured holiday rentals in Upperville
  • Use the map to find apartments and other holiday homes in the Upperville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Upperville while they last

Look no further and take a look at our great range of rental properties in Upperville!

Frequently asked questions

Can I find a holiday rental in Upperville?

Yes, there are holiday rentals close to the most popular sights in Upperville, or you can select a more secluded option if you're looking for a relaxing stay. Upperville is known for its restaurants.

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

Terra Alta - Incredible River Views and Hot Tub!: This holiday home rental outside of Upperville is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a private garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Upperville?

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

What can I see and do in Upperville?

While exploring the area, visit family-friendly sights like Dinosaur Land, 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 wider area.

What are holiday rentals like in Upperville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Upperville. Holiday rentals feature extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for families.