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Upperville Holiday Rentals

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Check prices for these dates

Tonight
11 Jan - 12 Jan
Tomorrow
12 Jan - 13 Jan
Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan

Our top choices for Upperville holiday rentals

TV, fireplace
Aslan's How - Cabin with Valley Views & Hot Tub!

Aslan's How - Cabin with Valley Views & Hot Tub!

Aslan's How - Cabin with Valley Views & Hot Tub!
2.0 star property
Harpers Ferry
9.8 out of 10, Exceptional, (8 reviews)
"We stayed here for our honeymoon and it was very nice and peaceful "
United States
Robert F.
The price is HK$779
HK$2,941 total
includes taxes & fees
13 Jan - 14 Jan
Aslan's How - Cabin with Valley Views & Hot Tub!
Living area
Wild Hare Cottage

Wild Hare Cottage

Wild Hare Cottage
Purcellville
10.0 out of 10, Exceptional, (10 reviews)
"Perfect spot to relax for a long weekend. Easy drive to Middleburg, VA, wineries, breweries, and hiking. Would stay again. "
United States
Jennifer K.
The price is HK$982
HK$1,697 total
includes taxes & fees
14 Jan - 15 Jan
Wild Hare Cottage
Interior
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

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

Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Harpers Ferry
9.2 out of 10, Wonderful, (30 reviews)
"Gorgeous cabin, incredibly clean and well stocked with everything needed. Hot tub was amazing and clean and huge. Greatful for the hosts promptness in communication.Thank you!"
United States
Samantha S.
The price is HK$1,298
HK$2,326 total
includes taxes & fees
14 Jan - 15 Jan
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
Dining
Log Cabin w/ Hot Tub & Waterfront Patio!

Log Cabin w/ Hot Tub & Waterfront Patio!

Log Cabin w/ Hot Tub & Waterfront Patio!
2.0 star property
Harpers Ferry
9.8 out of 10, Exceptional, (14 reviews)
"Everything was great! We had a lovely stay."
United States
Beth D.
The price is HK$779
HK$2,742 total
includes taxes & fees
19 Jan - 20 Jan
Log Cabin w/ Hot Tub & Waterfront Patio!
Interior
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
9.6 out of 10, Exceptional, (10 reviews)
"It was a great place to starve whole experience was perfect. "
United States
Jaime B.
The price is HK$1,754
HK$3,057 total
includes taxes & fees
13 Jan - 14 Jan
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Dining
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
Harpers Ferry
10.0 out of 10, Exceptional, (83 reviews)
"This is a super cute mountain cabin that has been completely redone with some pretty high end finishes. Our family thoroughly enjoyed our quick visit!"
United States
Sara S.
The price is HK$772
HK$2,134 total
includes taxes & fees
13 Jan - 14 Jan
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
Exterior
Lake View Retreat - Cottage Near a Peaceful Lake!

Lake View Retreat - Cottage Near a Peaceful Lake!

Lake View Retreat - Cottage Near a Peaceful Lake!
Harpers Ferry
9.6 out of 10, Exceptional, (21 reviews)
"The house was clean, had plenty of rooms and a fantastic location. "
United States
Bryan N.
The price is HK$779
HK$2,802 total
includes taxes & fees
15 Jan - 16 Jan
Lake View Retreat - Cottage Near a Peaceful Lake!
Interior
Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
10.0 out of 10, Exceptional, (31 reviews)
"Great location. Beautiful scenery. House was clean."
United States
Brandon H.
The price is HK$779
HK$2,837 total
includes taxes & fees
14 Jan - 15 Jan
Peaceful Lakefront Cottage with Mountain Views!
Outdoor dining
Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (23 reviews)
"My friends and I absolutely loved this stay on the lake in West Virginia! The artsy vibe of the home, views, and wildlife were amazing. Plenty of places to sit and catch up. The kitchen was well stocked with appliances (thank you for the local coffee!) Each adult having their own bedroom and full bath was a huge perk!"
United States
Matthew P.
The price is HK$857
HK$3,498 total
includes taxes & fees
15 Jan - 16 Jan
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Terrace/patio
Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
2.0 star property
Stephens City
10.0 out of 10, Exceptional, (1 review)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
The price is HK$1,017
HK$1,276 total
includes taxes & fees
13 Jan - 14 Jan
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Terrace/patio
Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (12 reviews)
"Property was just what we were looking for "
United States
Tim C.
The price is HK$1,052
HK$1,700 total
includes taxes & fees
13 Jan - 14 Jan
Mountain View Bungalow in Front Royal
Smart TV, fireplace
Blue Ridge Getaway - Sunset Views, A.T. Access

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

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
9.8 out of 10, Exceptional, (64 reviews)
"Comfortable, clean, welcoming, wonderful hot tub, great view from the porch!"
United States
Carol M.
The price is HK$779
HK$2,837 total
includes taxes & fees
13 Jan - 14 Jan
Blue Ridge Getaway - Sunset Views, A.T. Access
Terrace/patio
Woodsy Retreat with a Hot Tub and Seasonal Views!

Woodsy Retreat with a Hot Tub and Seasonal Views!

Woodsy Retreat with a Hot Tub and Seasonal Views!
Harpers Ferry
9.8 out of 10, Exceptional, (24 reviews)
"I highly recommend this cabin stay! It has absolutely everything you could need. Super clean and in a great area. Will definitely stay again if we get the chance."
United States
Claudia F.
The price is HK$779
HK$2,646 total
includes taxes & fees
13 Jan - 14 Jan
Woodsy Retreat with a Hot Tub and Seasonal Views!
Smart TV
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Harpers Ferry
10.0 out of 10, Exceptional, (16 reviews)
"Great location. Great house. Could not have asked for more. "
United States
A. Bland and D. T.
The price is HK$779
HK$2,929 total
includes taxes & fees
15 Jan - 16 Jan
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Smart TV, fireplace
Secluded Cabin a Stone's Throw From the A.T.!

Secluded Cabin a Stone's Throw From the A.T.!

Secluded Cabin a Stone's Throw From the A.T.!
Harpers Ferry
10.0 out of 10, Exceptional, (34 reviews)
"Great property to stay at. Very comfortable, quiet, and secluded. Would recommend this property to anyone. "
United States
Leonardf B.
The price is HK$779
HK$2,929 total
includes taxes & fees
15 Jan - 16 Jan
Secluded Cabin a Stone's Throw From the A.T.!
Terrace/patio
Rebels Rest - Cabin with Enchanting Sunset Views!

Rebels Rest - Cabin with Enchanting Sunset Views!

Rebels Rest - Cabin with Enchanting Sunset Views!
Harpers Ferry
9.8 out of 10, Exceptional, (31 reviews)
"Beautiful Sunsets, older cabin, not too steep of a drive up, outside deck is nice and fire pit area out front! Harper’s Ferry Area is cute and full of history! Be in shape to hike and climb while you are here, especially if you plan on doing a ghost walk after walking the town all day! 5 friends girls trip was great! "
United States
Teresa R.
The price is HK$779
HK$2,933 total
includes taxes & fees
15 Jan - 16 Jan
Rebels Rest - Cabin with Enchanting Sunset Views!
Outdoor spa tub
Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (20 reviews)
"Great view, very secluded"
United States
Matt s.
The price is HK$795
HK$2,961 total
includes taxes & fees
26 Jan - 27 Jan
Cottage w/ Hot Tub and 100-Mile Valley Views!
Outdoor spa tub
Cute cabin retreat near Shenandoah National Park and pet friendly!

Cute cabin retreat near Shenandoah National Park and pet friendly!

Cute cabin retreat near Shenandoah National Park and pet friendly!
Linden
9.4 out of 10, Exceptional, (13 reviews)
"Fun location near tons of wineries, bowling, trails, and mountain living. Place is really nice with a grill, solo stove, kfantastic kitchen"
United States
Bret L.
The price is HK$954
HK$2,643 total
includes taxes & fees
20 Jan - 21 Jan
Cute cabin retreat near Shenandoah National Park and pet friendly!
Exterior
Private A-Frame Near Harpers Ferry - Sauna, Fire Pit, 3BR/3BA, Pet-Friendly

Private A-Frame Near Harpers Ferry - Sauna, Fire Pit, 3BR/3BA, Pet-Friendly

Private A-Frame Near Harpers Ferry - Sauna, Fire Pit, 3BR/3BA, Pet-Friendly
2.0 star property
Harpers Ferry
10.0 out of 10, Exceptional, (2 reviews)
"Very clean, great amenities, comfortable!"
United States
James
The price is HK$1,247
HK$3,913 total
includes taxes & fees
13 Jan - 14 Jan
Private A-Frame Near Harpers Ferry - Sauna, Fire Pit, 3BR/3BA, Pet-Friendly
Terrace/patio
Historic Bluemont Village Home

Historic Bluemont Village Home

Historic Bluemont Village Home
Bluemont
10.0 out of 10, Exceptional, (39 reviews)
"This was one of the best VRBO experiences I’ve had! Communication with the host was exceptional, and the home itself was gorgeous. It’s clear they have put a lot of thought into make this house a perfect getaway — it is beautifully decorated and has all the comforts of home. We will definitely stay here again!"
United States
Mary S.
The price is HK$1,228
HK$3,337 total
includes taxes & fees
13 Jan - 14 Jan
Historic Bluemont Village 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

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

10/10 Excellent
"C'était propre et tranquille"
Carole 1-night trip
Posted 23 hours 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:

  • 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?

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry: This holiday home rental outside of Upperville is located in the mountains, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.