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Compare 219 Vacation Homes in Round Hill with updated reviews, rates, and availability.

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

9.8 out of 10, Exceptional, (242)
"We thoroughly enjoyed the cozy lodge vibe and the different spaces it offered our group. The host, Leslie, was always available for any questions we had. She also had the place decorated for Christmas which warmed our hearts!! Thank you Bear Chase for a great weekend. "
Breathtaking views with an indoor private pool, come escape with us

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (52)
"Está bien hermosa la casa "
The price is SAR 1,044
SAR 2,437 total
includes taxes & fees
26 Dec - 27 Dec
Terra Alta - Incredible River Views and Hot Tub!

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (40)
"Lots of space for everyone, excellent pool and hot tub"
Charles Town Home w/ Private Pool & Hot Tub

Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

10.0 out of 10, Exceptional, (62)
"We were looking for the perfect place to stay during our week in hunt country- convenient to the farm where we kept our horses and the restaurants in Middleburg. This exceeded our expectations. This house has been lovingly restored and is beautifully decorated. Its cozy, traditional vibe meshes perfectly with its modern updates. There are thoughtful touches everywhere- from a large selection of coffees, to the working fireplace, and many more. The beds and bedding are super comfortable. We...
Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

10.0 out of 10, Exceptional, (95)
"The home was in excellent condition, clean, beautiful and overall lovely. Close to Middleburg, a delightful small town. We felt like we were in the country, but close to everything we wanted to do."
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

Charming 3-Bedroom Home in historic Harpers Ferry: No Pet or Cleaning Fees!

10.0 out of 10, Exceptional, (12)
"Harper’s Ferry is amazing and the property is in the heart of it. Walk to the historical sites or Trail store. Park and ride is less than 5 mins to catch train to DC. Home has a modernized restoration with beautiful aesthetics inside. Large deck with smokeless firepit. Back yard is gated for pups. Many thoughtful amenities. Professionally clean. Nice owners. 10/10"
Charming 3-Bedroom Home in historic Harpers Ferry: No Pet or Cleaning Fees!

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

9.8 out of 10, Exceptional, (88)
"Great year round location. Owners are nearby if issues occur. HIGHLY RECOMMENDED. "
The price is SAR 545
SAR 828 total
includes taxes & fees
26 Dec - 27 Dec
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

10.0 out of 10, Exceptional, (110)
"This property could not have been more quaint and peaceful. My husband, two dogs and I enjoyed the long weekend, walking the trails and taking in the history of Harper’s Ferry. I would highly recommend this property to anyone looking for a quiet getaway. The location could not be better for seeing the town on foot. The property was clean and so neatly appointed. Breathtaking views! "
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Walk to Potomac River and downtown Harpers Ferry

10.0 out of 10, Exceptional, (110)
"The house was amazing, great views and a great layout that allowed for us to hang as a group or have some privacy. Very convenient to everything we wanted to do; Harper’s Ferry, Ziplining (or rafting based on time of year), and the Brewery that we went to on the last night felt like it was almost walking distance. Definitely recommend and would stay again in a heartbeat. "
Walk to Potomac River and downtown Harpers Ferry

The PINK PEARL in Historic Leesburg

9.6 out of 10, Exceptional, (31)
"Loved the location and ability to sleep 8 people. Great for a weekend stay!"
The PINK PEARL in Historic Leesburg

Stunning House! Minutes From Shenandoah River

10.0 out of 10, Exceptional, (18)
"Lovely and well maintained home in a quiet neighborhood!"
Stunning House! Minutes From Shenandoah River

A 3-bedroom house just a 20-minute walk from historic Harpers Ferry.

10.0 out of 10, Exceptional, (1)
"Raisa's place was quaint and more than adequate. It was neat and had many interesting plants throughout the house. The backyard was great to have (especially being pet friendly). Access to Harper's Ferry was close by and very convenient. Recommend!"
A 3-bedroom house just a 20-minute walk from historic Harpers Ferry.

Cozy Country Getaway in the Heart of Upperville

10.0 out of 10, Exceptional, (7)
"Highly recommend this place."
Cozy Country Getaway in the Heart of Upperville

Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country

9.6 out of 10, Exceptional, (13)
"We had a small family gathering here around Christmas and we absolutely loved it! We immediately felt right at home. It is a gorgeous property, well appointed, and very comfortable. The game room was a huge hit with everyone. We're hoping to make it an annual tradition, hopefully for longer than one night next time!"
The price is SAR 1,762
SAR 2,111 total
includes taxes & fees
14 Jan - 15 January 2025
Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country

Romantic Stone Cottage Circa 1869-75 acres to Hike

9.2 out of 10, Wonderful, (5)
"Unfortunately we happened to stay when there was a wind storm in the county so we lost power, water and heat for the night. We texted the host to check on candles and/or flashlights but were told to “just use our phones”. (Not really an option when you’ve been traveling all day and phones are almost dead). The cottage is very rustic and not quite as comfortable as the pictures make it out to be. The bed is extremely firm so be aware if you have bad hips or back. There’s also glade plug ins in...
Romantic Stone Cottage Circa 1869-75 acres to Hike

Charming 4-bedroom Estate - A Historic Gem in Clarke County, VA

Charming 4-bedroom Estate - A Historic Gem in Clarke County, VA

Quaint Royal Cottage @ Historic Leesburg

2.0 star property
The price is SAR 939
SAR 1,966 total
includes taxes & fees
30 Dec - 31 Dec
Quaint Royal Cottage @ Historic Leesburg

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, (92)
"Wonderful Thanksgiving in a wonderful home with our family."
Gruner Bungalow at Otium Cellars

Pet-Friendly Retreat: Relax w/HotTub, Custom FirePit & Walk to Town/Trails!

10.0 out of 10, Exceptional, (11)
"We hosted Thanksgiving weekend at the house and it perfectly accommodated our large group as well as the varying ages (31-89). House is well organized and amenities were all as described. Plenty of dishwater and glasses for a large group although if you are hosting a large meal bring some disposable platters and a cocktail shaker. Few minutes drive to Purcellville which had plenty of options for live sports and other dinners. Beautifully decorated with plenty of space. Also nice to be at the...
Pet-Friendly Retreat: Relax w/HotTub, Custom FirePit & Walk to Town/Trails!
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 property types in Round Hill

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

9.8 out of 10, Exceptional, (242)
"We thoroughly enjoyed the cozy lodge vibe and the different spaces it offered our group. The host, Leslie, was always available for any questions we had. She also had the place decorated for Christmas which warmed our hearts!! Thank you Bear Chase for a great weekend. "
Breathtaking views with an indoor private pool, come escape with us

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (48)
"Excellent little cabin right on the river and close to DT Sheperdstown which is a great town."
The price is SAR 165
SAR 412 total
includes taxes & fees
30 Dec - 31 Dec
❤️ Secluded 1940s Romantic Tiny House on the River

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (52)
"Está bien hermosa la casa "
The price is SAR 1,044
SAR 2,437 total
includes taxes & fees
26 Dec - 27 Dec
Terra Alta - Incredible River 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.