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Compare 206 Vacation Homes in Hillsboro with updated reviews, rates, and availability.

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
View of High Street in Downtown Harpers Ferry from front porch
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
10.0 out of 10, Exceptional, (101)
"Great location, loved the "
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Charles Town Home w/ Private Pool & Hot Tub
Charles Town Vacation Rental | 5BR | 3.5BA | Stairs Required | 5,600 Sq Ft
Charles Town Home w/ Private Pool & Hot Tub
10.0 out of 10, Exceptional, (33)
"This property is like a self-contained vacation getaway with everything. The house has a mini movie theater, pool table, ping pong table, and tons of games. And the pool with the water slide is AMAZING. Add the gas-powered charcoal fire pit was great for an evening campfire and roasting marshmallows. Everyone had a BLAST. The management company and owner are also EXTREMELY helpful and responsive. Only minor issues worth mentioning are that the listing says there are two pull-out coaches which...
Charles Town Home w/ Private Pool & Hot Tub
Breathtaking views with an indoor private pool, come escape with us
Exterior
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (235)
"We were so excited to see that the Bear Chase Manor was available for the weekend of my daughter’s wedding. We knew this house would allow our family to enjoy the beautiful views and build lifelong memories. It was the perfect house for our special weekend. I highly recommend this house! "
Breathtaking views with an indoor private pool, come escape with us
Harpers Ferry Luxury, Spa Bathroom, Movie Room
Bathroom
Harpers Ferry Luxury, Spa Bathroom, Movie Room
9.4 out of 10, Exceptional, (13)
"Perfect getaway! The place was spotless, and the movie room was our favorite spot. We loved the design of the house and the town has so much charm. Can't wait to come back!"
Harpers Ferry Luxury, Spa Bathroom, Movie Room
Terra Alta - Incredible River Views and Hot Tub!
Soak in the tub while enjoying the beautiful view of the river below!
Terra Alta - Incredible River Views and Hot Tub!
9.8 out of 10, Exceptional, (50)
"I recommend this house for the Harpers Ferry location. Four spacious bedrooms, three bathrooms, hot tub, and games."
Terra Alta - Incredible River Views and Hot Tub!
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Living Room
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
9.8 out of 10, Exceptional, (76)
"This home is in a great location for visiting all of the historic areas and excellent wineries. It has all of the comforts of home AND with an amazing view. The home is picture perfect - warm and welcoming and wonderfully decorated. We look forward to returning again."
The price is AED 533
AED 813 total
includes taxes & fees
24 Sep - 25 Sep
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
WV Cozy Cabin Summit Point Races
Exterior
WV Cozy Cabin Summit Point Races
9.8 out of 10, Exceptional, (18)
"no issues, had a great time"
WV Cozy Cabin Summit Point Races
Townhome in Leesburg Historic District!
Leesburg Vacation Rental | 2BR | 1BA | 1,000 Sq Ft | Steps Required
Townhome in Leesburg Historic District!
10.0 out of 10, Exceptional, (16)
"Lovely property and well appointed. Close to bars and restaurants and lovely outside area"
Townhome in Leesburg Historic District!
Charming 3-Bedroom Home in Harpers Ferry Historic District: Walk to Attractions!
Exterior
Charming 3-Bedroom Home in Harpers Ferry Historic District: Walk to Attractions!
10.0 out of 10, Exceptional, (9)
"We had a nice weekend and enjoyed your place, very comfortable and clean!"
Charming 3-Bedroom Home in Harpers Ferry Historic District: Walk to Attractions!
Cozy home near Casino, Breweries, Historical attractions, National Park & more
The Wilt House! Cozy, quaint vintage cape cod. Walk to Charles Town and Casino
Cozy home near Casino, Breweries, Historical attractions, National Park & more
10.0 out of 10, Exceptional, (19)
"Beautiful home will def get again"
Cozy home near Casino, Breweries, Historical attractions, National Park & more
Renovated WV Schoolhouse: History Buff’s Heaven!
Kearneysville Vacation Rental | 1BR | 1BA | Single Story | 3 Steps Required
Renovated WV Schoolhouse: History Buff’s Heaven!
10.0 out of 10, Exceptional, (42)
"Very unique and nostalgic!"
Renovated WV Schoolhouse: History Buff’s Heaven!
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Living room
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
9.8 out of 10, Exceptional, (112)
"Beautiful home that has an antique feel with modern convenience. The host was very attentive and helpful. The area is gorgeous and steeped in history, with lots to see and do."
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Charming "Cream of the Crop" Cape ~❤️of Middletown
Exterior
Charming "Cream of the Crop" Cape ~❤️of Middletown
10.0 out of 10, Exceptional, (109)
"It is exactly as described. Comfortable, convenient to all of places that we needed to go while in Middletown. If family matters again require a visit to the area, we will definitely book again."
The price is AED 547
AED 1,149 total
includes taxes & fees
29 Sep - 30 Sep
Charming "Cream of the Crop" Cape ~❤️of Middletown
Spacious Riverview Escape: Just Half Mile to Harpers Ferry National Park Center
Property grounds
Spacious Riverview Escape: Just Half Mile to Harpers Ferry National Park Center
9.8 out of 10, Exceptional, (8)
"This is an immaculately clean property at the end of the road with no traffic. All new appliances. Located between historic old town and adventure outing companies. Great back deck. Highly recommend!"
Spacious Riverview Escape: Just Half Mile to Harpers Ferry National Park Center
Enchanting Cottage, walk to Downtown Harpers Ferry
Enchanting Cottage, walk to Downtown Harpers Ferry
10.0 out of 10, Exceptional, (33)
"The cottage was very quaint. Peaceful. Walked to Harper's Ferry. Did some hiking. When into Charles Town to antique shop. Went to the Harper's Ferry Brewery."
The price is AED 967
AED 1,544 total
includes taxes & fees
22 Oct - 23 Oct
Enchanting Cottage, walk to Downtown Harpers Ferry
*Daley's Doll House At Antietam*
HOUSE - front of this cute little one bedroom, one bath dollhouse.
*Daley's Doll House At Antietam*
9.8 out of 10, Exceptional, (91)
"The Dollhouse was perfect for us & our 2 pups! Comfortable and really close to all the Civil War sites. The Antietam Creek Winery is really close & well worth the visit especially on live entertainment nights."
*Daley's Doll House At Antietam*
Trouvaille House Suite #3 “Klimt” Suite
Klimt Suite
Trouvaille House Suite #3 “Klimt” Suite
9.8 out of 10, Exceptional, (26)
"Instructions were clear and host was quick with responses. The place was clean and quiet. And who doesn't like Harpers Ferry?"
The price is AED 643
AED 1,002 total
includes taxes & fees
13 Oct - 14 Oct
Trouvaille House Suite #3 “Klimt” Suite
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
Property grounds
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
10.0 out of 10, Exceptional, (87)
"My family has stayed at Yellowwood in the past and had an excellent experience. We returned again this time and had another great experience. The owner and property manager are responsive and pleasant to deal with. The house is perfect for a family. The location is excellent for anyone interested in visiting Middleburg or the surrounding area. Stronly recommended. "
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
Family Retreat w/ Deck Near Appalachian Trail!
Berryville Vacation Rental | 4BR | 3.5BA | 4,384 Sq Ft | 1 Exterior Step
Family Retreat w/ Deck Near Appalachian Trail!
10.0 out of 10, Exceptional, (34)
"The property description and photographs are accurate, and the hostess, Kathryn, is tremendous! This is the second stay for my wife and I, our two adult children, my mother- and father-in-law, and our three Australian Shepherds. Although hot weather and frequent thunderstorms limited outdoor activities and excursions last summer, we had such a pleasant time relaxing and enjoying the property's indoor amenities that we decided to come back again this year. With fantastic weather the entire...
Family Retreat w/ Deck Near Appalachian Trail!
Elegant Middleburg Manor with 3 Bedrooms 2 Baths
Exterior
Elegant Middleburg Manor with 3 Bedrooms 2 Baths
10.0 out of 10, Exceptional, (40)
"Property is a very short distance to downtown Middleburg. Cute and clean property. property manager responds quickly to questions. Wifi is not very fast so if this is important to you you may want to connect with property manager to determine if it will meet your needs. "
Elegant Middleburg Manor with 3 Bedrooms 2 Baths
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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 Hillsboro

Breathtaking views with an indoor private pool, come escape with us
Exterior
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (235)
"We were so excited to see that the Bear Chase Manor was available for the weekend of my daughter’s wedding. We knew this house would allow our family to enjoy the beautiful views and build lifelong memories. It was the perfect house for our special weekend. I highly recommend this house! "
Breathtaking views with an indoor private pool, come escape with us
RIVERKEEPER INN, Waterfront Property on the Potomac River
Private Waterfront Deck with swing goes with rental
RIVERKEEPER INN, Waterfront Property on the Potomac River
9.2 out of 10, Wonderful, (111)
"We had a wonderful weekend! Everything was perfect. Great human hosts and dog host! Thank you!"
RIVERKEEPER INN, Waterfront Property on the Potomac River
❤️ Secluded 1940s Romantic Tiny House on the River
❤️ Secluded 1940s Romantic Tiny House on the River
10.0 out of 10, Exceptional, (43)
"Absolutely amazing 😍😍"
The price is AED 162
AED 403 total
includes taxes & fees
14 Oct - 15 Oct
❤️ Secluded 1940s Romantic Tiny House on the River
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.