Round Hill Holiday Rentals

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Holiday Rentals in Round Hill

The Lodge at Stoneleigh

10.0 out of 10, Exceptional, (7)
"Great house; perfect for family with lots of activities in the area as well."
The Lodge at Stoneleigh

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (36)
"Adorable cottage. Well appointef"
The price is AU$623
includes taxes & fees
17 Feb - 18 Feb
18th Century Stone Cottage minutes from historic Middleburg

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (53)
"The cabin was perfect for a few days of writing and reflecting! Everything was very clean and it was easy communicating with the owner. The house is not "secluded" as there are neighboring houses on two sides and if I hadn't brought an ax/saw to cut my own dry wood enjoying a fire wouldn't have been possible. But overall a lovely stay and I look forward to going again!"
The price is AU$176
includes taxes & fees
24 Feb - 25 Feb
❤️ Secluded 1940s Romantic Tiny House on the River

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

9.8 out of 10, Exceptional, (244)
"Our group had an amazing stay at the Bear Chase Manor! The house has great common space areas and the pool was a huge hit with everyone. We also loved the convenience of being next to the brewery along with the incredible views of nature. Can't wait to have the opportunity to stay here again!"
Breathtaking views with an indoor private pool, come escape with us

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (43)
"We had an excellent stay at Jill’s VRBO! The home was spacious and clean, perfect for a relaxing weekend away. The location also is ideal for going to wineries near Leesburg and Middleburg. And Jill was a very attentive host— she made sure that someone was there to remove the snow from the driveway and responded to any messages we sent promptly."
Trailside Retreat in breathtaking Western Loudoun

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

10.0 out of 10, Exceptional, (79)
"My husband and I had a lovely stay in this cabin for Thanksgiving. We had everything we needed to cook our Thanksgiving meal, stay cozy, and enjoy the views around the cabin. Thank you!"
Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!

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 AU$571
includes taxes & fees
25 Feb - 26 Feb
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

Cute cabin retreat near Shenandoah National Park and pet friendly!

9.2 out of 10, Wonderful, (10)
"Fun location near tons of wineries, bowling, trails, and mountain living. Place is really nice with a grill, solo stove, kfantastic kitchen"
Cute cabin retreat near Shenandoah National Park and pet friendly!

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.8 out of 10, Exceptional, (90)
"We had a wonderful stay at the Riverside cabin. With a beautiful view, perfect deck for reading, and a quiet house to get away in. So close to town and activities provided for a wonderful getaway. "
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (17)
"Great experience. Cabin is as shown, very comfortable, easy access. 10 min to Shepherdstown, lots of great restaurants and shops there. Our dates ended up being over the severe cold/snow in January 2025, so we didn't do much hiking or anything on the river, but it was a lovely environment, very peaceful and cozy. Owners were super responsive when needed and very easy to work with. Would definitely go back in nicer weather! "
Charming Cabin in the Woods with River Access

Cozy Mountain Cabin w/ Steam Shower. Great for Couples!

10.0 out of 10, Exceptional, (54)
"The cabin was very nice and quaint. We had a nice stay. The view from the sunroom is great amazing. The place is very cozy and made for a great night away. "
The price is AU$478
includes taxes & fees
24 Feb - 25 Feb
Cozy Mountain Cabin w/ Steam Shower. Great for Couples!

Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

10.0 out of 10, Exceptional, (25)
"What a great home. The host obviously took the extra steps to make sure guests are comfortable and well cared for. Very cozy!"
The price is AU$439
includes taxes & fees
23 Feb - 24 Feb
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

White House Inn - Historic Home in Harpers Ferry!

10.0 out of 10, Exceptional, (28)
"We very much enjoyed our stay at this property. Walking distance to Harper's ferry attractions and plenty of room for 5 adults to spread out. We anticipate renting this property in the future for more ladies weekends!"
The price is AU$645
includes taxes & fees
17 Feb - 18 Feb
White House Inn - Historic Home in Harpers Ferry!

Walk to Potomac River and downtown Harpers Ferry

10.0 out of 10, Exceptional, (111)
"The house was a perfect size for my group of 10. We stayed for my birthday weekend and the house was very stocked with cleaning supplies, sheets, pillows, towels, etc. Michael was very responsive and even sent a huge list of recommendations in the area. If I'm ever in the area again, I will definitely be staying here!!!"
Walk to Potomac River and downtown Harpers Ferry

Front Royal Hilltop Cabin w/ Panoramic Views!

10.0 out of 10, Exceptional, (30)
"Five of us really enjoyed our weekend. Beautiful home with a great views. Greg made sure we had everything we needed. Would love to stay again. "
Front Royal Hilltop Cabin w/ Panoramic Views!

Happy Harbor | Mtn + Riverside w/ Game Room + Water Hole!

8.8 out of 10, Excellent, (21)
"Our large family loved coming together at this beautiful home! We enjoyed sitting around the large kitchen and beautiful living room while the teens and kids enjoyed the game room and the basketball area. We also loved having a large property to explore"
Happy Harbor | Mtn + Riverside w/ Game Room + Water Hole!

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

2.0 star property
10.0 out of 10, Exceptional, (4)
"What a great stay. "
The price is AU$604
includes taxes & fees
20 Feb - 21 Feb
Aslan's How - Cabin with Valley Views & Hot Tub!

Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly

10.0 out of 10, Exceptional, (33)
"Great house! Lots of room and cozy. Even saw some deer! Highly recommend!"
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly

Best location! The Pullman Apt @ historic 1799 Inn

9.6 out of 10, Exceptional, (29)
"Did everything I wanted to do in Harpers Ferry hiked the Maryland Heights Trail explore the town and watched the trains pass by "
The price is AU$282
includes taxes & fees
23 Feb - 24 Feb
Best location! The Pullman Apt @ historic 1799 Inn

Gruner Bungalow at Otium Cellars

9.8 out of 10, Exceptional, (93)
"It's was great. We visited family in the area. And had our family Christmas together at this place. We played ping pong and pool when we where there. Great location for dogs. Plenty of space to run and play. The house was great as well. Plenty of space for everyone."
Gruner Bungalow at Otium Cellars
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 Round Hill you may be interested in

Lansdowne Resort and Spa

4.0 star property
8.6 out of 10, Excellent, (1002)
"Wonderful"
The price is AU$364
includes taxes & fees
20 Feb - 21 Feb
Lansdowne Resort and Spa

Salamander Resort And Spa

5.0 star property
9.2 out of 10, Wonderful, (338)
"Salamander is living up to its reputation for being elegant and upscale. But it's the staff, the food, and the overall excellent working conditions of everything that make this a wonderful place to stay."
The price is AU$1,069
includes taxes & fees
17 Feb - 18 Feb
Salamander Resort And Spa

La Quinta Inn & Suites by Wyndham Winchester

2.5 star property
9.2 out of 10, Wonderful, (1815)
"Clean comfortable room. Great hot breakfast."
The price is AU$172
includes taxes & fees
18 Feb - 19 Feb
La Quinta Inn & Suites by Wyndham Winchester
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

Are there holiday rentals in Round Hill?

Yes, there are holiday rentals in Round Hill close to Hill High Country Store, or you can select a more secluded option if you're looking for a relaxing stay. Round Hill is known for its golf courses and art.

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

Riverside cottage, minutes from historic Harpers Ferry! Private river access!: This holiday home rental outside of Round Hill offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Round Hill?

Choose from 6 Expedia holiday rentals in Round Hill for a memorable holiday.

What can I see and do in Round Hill?

Hill High Country Store and K & S Pewter are a couple of the family-friendly sights, whereas cultural attractions include Round Hill Arts Center. Stoneleigh Golf and Country Club and Bogati Bodega & Winery are other places to visit while you're in town.

What are holiday rentals like in Round Hill?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Round Hill. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you a great travel experience. 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 a family trip.