Holiday Rentals in Upperville

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Holiday Rentals in Upperville

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

9.8 out of 10, Exceptional, (240)
"Great place to relax & enjoy! We loved the pool & hot tub as well abundant indoor/outdoor space. There was a musty smell that lingered on all my clothes and I stayed in the very top floor master & put my clothes in dresser and closet. You may need a dehumidifier in that closet…."
Breathtaking views with an indoor private pool, come escape with us

The Oculus - Huge Cabin with a Hot Tub!

9.8 out of 10, Exceptional, (15)
"Rustic."
The Oculus - Huge Cabin with a Hot Tub!

Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

10.0 out of 10, Exceptional, (51)
"Comfy cabin with everything topline. Loved the sunroom and the steam shower. Daily watching deer feed and stroll through the yard below. Gus wasn’t happy about it but he still watched through floor to ceiling windows."
The price is €296
includes taxes & fees
11 Dec - 12 Dec
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

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

9.8 out of 10, Exceptional, (46)
"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 €374
includes taxes & fees
12 Dec - 13 Dec
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!

10.0 out of 10, Exceptional, (76)
"Whisky Hill is an amazing cabin. My husband and I enjoyed our stay. Everything was clean, and had everything we needed. It was not difficult at all to find. We thoroughly enjoyed our time and can’t wait to be back. It was a great find!! Highly recommend if coming to the Linden area. "
Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!

Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!

9.8 out of 10, Exceptional, (19)
"My friends and I always choose a new cabin for our annual fall getaway. We've not had a bad experience yet. Mountain Mama's Woodpecker Woods did not disappoint, either! Comfortable, warm, clean, spacious log cabin. It had everything we needed. In fact, it was so relaxing, we never made it to the hot tub. We did visit Harper's Ferry Park and enjoyed walking the hiking trail to the downtown area. :-) We especially loved the close proximity to the Washington, DC Metro area. If there was anything...
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (32)
"Nice place! Clean, beautiful, and located just two miles from town. "
The price is €386
includes taxes & fees
9 Dec - 10 Dec
18th Century Stone Cottage minutes from historic Middleburg

Hot Tub, Poker Table, River Access & Kayaks and Wineries

9.6 out of 10, Exceptional, (17)
"My extended family met in Harper’s Ferry for a hiking weekend, and this was a perfect home base! Enough room for 8 of us plus dogs, and a beautiful outdoor space. We will definitely be back!"
The price is €408
includes taxes & fees
2 Dec - 3 Dec
Hot Tub, Poker Table, River Access & Kayaks and Wineries

Beautifully Restored Log Cabin in Bluemont, VA

10.0 out of 10, Exceptional, (34)
"This was a very beautiful place to stay. The host was extremely communicative and made sure I knew she was available if needed. I enjoyed the history of the cabin and the information provided about it. I would highly recommend staying here for anyone looking for a cozy place to stay. "
Beautifully Restored Log Cabin in Bluemont, VA

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

9.8 out of 10, Exceptional, (25)
"Hiking, playing in the creek, S'mores by the fire pit, enjoying meals on the porch all add up to fun memories. We enjoyed our stay. "
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

Gruner Bungalow at Otium Cellars

9.8 out of 10, Exceptional, (87)
"This was our third time staying at this beautiful property for our strategic planning session, and once again, it was a fantastic experience. The house is always spotless, spacious, and beautifully decorated, making it feel like a true home away from home. The host provided delicious meals throughout our stay, which added an extra level of convenience and enjoyment. Each meal was thoughtfully prepared and absolutely delicious—perfect for keeping our team energized and focused. The peaceful...
Gruner Bungalow at Otium Cellars

Quiet Retreat in the Woods- HOT TUB, Arcade, Fire Pit

9.2 out of 10, Wonderful, (10)
"Week with elderly family members and this home was a good spot to rest and relax. Upon arrival, house was neat and clean. Well stocked with cooking items. Nice layout. Good central locations for day trip options. Overall I would recommend this home. "
Quiet Retreat in the Woods- HOT TUB, Arcade, Fire Pit

Rustic Log Cabin with Private Dock on the Lake!

9.8 out of 10, Exceptional, (11)
"Amazing location!!! 18 minutes from a cluster of wineries; quiet and relaxing. Definitely will be visiting again "
Rustic Log Cabin with Private Dock on the Lake!

Bear Chase Cottage

10.0 out of 10, Exceptional, (30)
"Everything about the Cottage was amazing. Not sure when it was built/remodeled, but it seemed brand new! The size was perfect for a small friend group bday getaway. The location is ideal. Can’t wait to go back. "
Bear Chase Cottage

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

10.0 out of 10, Exceptional, (47)
"Our stay was perfect "
The price is €510
includes taxes & fees
1 Dec - 2 Dec
Blue Ridge Getaway - Sunset Views, A.T. Access

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (36)
"My wife and I really enjoyed our stay in Paris. William was the perfect host and provided us detailed information prior to our arrival. Everything we needed was provided to us in the cottage. The location was perfect to access Sky Meadows State Park and several wineries. We enjoyed the extra amenities, such as the backyard fire pit, loft media room, and the grill. "
The price is €296
includes taxes & fees
12 Dec - 13 Dec
Historical cottage in the town of Paris

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

9.8 out of 10, Exceptional, (17)
"We were charmed by the house and pleased with all the amenities. We would definitely stay there again. "
Secluded Cabin a Stone's Throw From the A.T.!

Rebels Rest - Cabin with Enchanting Sunset Views!

9.8 out of 10, Exceptional, (27)
"It was as advertised. The house had everything needed for an enjoyable stay"
Rebels Rest - Cabin with Enchanting Sunset Views!

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (44)
"Perfect. No complaints at all. Thank you again. "
The price is €315
includes taxes & fees
17 Dec - 18 Dec
Cottage on King | Charming Historic Leesburg Home

Insta Worthy Mountain Views and Hot Tub

10.0 out of 10, Exceptional, (8)
"This mountain house is absolute beauty! It is beyond gorgeous. The view is spectacular, the sunset is breathtaking. You have a 180 degrees view of West VA. The house itself is stunning, plenty of rooms to move around with our group of 15. We enjoyed the jacuzzi while admiring the beautiful sunset. The kids had fun roasting marshmallows while Eagles are flying up above them. Thank you for sharing this Eagle’s Nest home. 😊"
The price is €971
includes taxes & fees
2 Dec - 3 Dec
Insta Worthy Mountain Views and Hot Tub
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 types of properties in Upperville you may be interested in

La Quinta Inn & Suites by Wyndham Winchester

2.5 star property
9.2 out of 10, Wonderful, (1748)
"We’ve stayed here multiple times as it is a half way point on our bi-annual roadtrip to visit family. Easy access to highway, restaurants (dining and takeout), and the staff is great."
The price is €95
includes taxes & fees
1 Dec - 2 Dec
La Quinta Inn & Suites by Wyndham Winchester

Lansdowne Resort and Spa

4.0 star property
8.6 out of 10, Excellent, (964)
"Everything was excellent from start to finish. The staff was very friendly as always and our rooms were clean and spacious. We will come back again next year."
The price is €212
includes taxes & fees
22 Dec - 23 Dec
Lansdowne Resort and Spa

Salamander Resort And Spa

5.0 star property
9.2 out of 10, Wonderful, (322)
"Lovely, pretty and toney hotel with a spacious comfortable room. Service is friendly and very efficient. Nice expansive grounds. But dining options in this large hotel are limited and there is that annoying resort fee tacked on the daily bill. Dining options in town are also not very expansive."
The price is €652
includes taxes & fees
17 Dec - 18 Dec
Salamander Resort And Spa
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.

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?

Breathtaking views with an indoor private pool, come escape with us: This holiday home rental outside of Upperville is located in the mountains, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 6 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 balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Upperville?

Choose from 4 Expedia holiday rentals in Upperville for a memorable holiday.

What can I see and do in Upperville?

Sky Meadows State Park and Upperville Park are a couple of lovely local spots to get outside and enjoy nature. Delaplane Cellars and Barrel Oak Winery 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.