Hillsboro Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Hillsboro holiday rentals

Exterior

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (74 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is HK$522
HK$1,057 total
includes taxes & fees
26 May - 27 May
❤️ Secluded 1940s Romantic Tiny House on the River
Interior

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
9.6 out of 10, Exceptional, (114 reviews)
"Good stay. Would visit again. "
United States
Lonnie F.
The price is HK$587
HK$1,544 total
includes taxes & fees
19 May - 20 May
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Dining

~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!

~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!
Harpers Ferry
10.0 out of 10, Exceptional, (88 reviews)
"The host had great communication and the place was exactly as pictured! "
United States
Colleen J.
The price is HK$1,309
HK$2,842 total
includes taxes & fees
19 May - 20 May
~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!
Exterior

Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (145 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is HK$666
HK$1,876 total
includes taxes & fees
19 May - 20 May
Charming "Cream of the Crop" Cape ~❤️of Middletown
Interior

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

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
9.8 out of 10, Exceptional, (16 reviews)
"GREAT stay…loved the location, the hot tub, the amenities, and the host."
United States
Domenic E.
The price is HK$1,762
HK$3,098 total
includes taxes & fees
19 May - 20 May
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Property grounds

Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (89 reviews)
"Did a small girls night here and we had the best time! Out there and quiet for a get away and plenty to do inside for colder weather we loved the bookshelf full of board games and books and the piano to tinker around on! The gas fireplace kept the whole place cranking with heat no problems Definitely would stay here again!"
United States
Kandy T.
The price is HK$1,566
HK$2,582 total
includes taxes & fees
19 May - 20 May
Antietam Creek - Quiet 2 Bedroom Cabin
Smart TV, books, computer monitors

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (34 reviews)
"Adorable, comfy, private & well appointed. Well cleared of snow for our arrival after a difficult snow/ice storm. Comfortable mattress was a bonus. We enjoyed our stay! "
United States
Amy M.
The price is HK$1,233
HK$2,607 total
includes taxes & fees
20 May - 21 May
Leesburg Hideaway- King Bed + Private Backyard
Exterior

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Sharpsburg
9.6 out of 10, Exceptional, (200 reviews)
"We enjoyed our stay and the location was excellent"
United States
Barbara W.
The price is HK$1,135
HK$1,370 total
includes taxes & fees
19 May - 20 May
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Interior

Secluded cabin w/hot tub & deck, dog-friendly

Secluded cabin w/hot tub & deck, dog-friendly
Harpers Ferry
9.2 out of 10, Wonderful, (33 reviews)
"Enjoyed the levels, hot tub, porch to get outside with my coffee, pet strolling area marvelous and washer/dryer."
United States
tracey b.
The price is HK$1,483
HK$2,585 total
includes taxes & fees
19 May - 20 May
Secluded cabin w/hot tub & deck, dog-friendly
Exterior

Beautiful, Historic, Hiking, Biking and C&O Canal

Beautiful, Historic, Hiking, Biking and C&O Canal
Brunswick
10.0 out of 10, Exceptional, (24 reviews)
"The host was extremely welcoming and kind to us. We spent a week here and loved our stay. We are so grateful to have been able to stay here with Kim and Todd. "
United States
Christina H.
The price is HK$904
HK$1,556 total
includes taxes & fees
20 May - 21 May
Beautiful, Historic, Hiking, Biking and C&O Canal
Fridge, microwave, oven, stovetop

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Jefferson
9.8 out of 10, Exceptional, (63 reviews)
"The beds were incredibly comfortable. Great house. Great location. "
United States
Julie B.
The price is HK$1,057
HK$2,274 total
includes taxes & fees
26 May - 27 May
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Exterior detail

Cozy Getaway near Harper`s Ferry, C&O & Potomac

Cozy Getaway near Harper`s Ferry, C&O & Potomac
Brunswick
9.8 out of 10, Exceptional, (60 reviews)
"Host was welcoming and place was as described and in very clean condition. "
United States
Junaid B.
The price is HK$775
HK$1,403 total
includes taxes & fees
20 May - 21 May
Cozy Getaway near Harper`s Ferry, C&O & Potomac
Property grounds

Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (44 reviews)
"Loved the place and area."
United States
Steve R.
The price is HK$1,506
HK$2,644 total
includes taxes & fees
25 May - 26 May
Charming Cabin in the Woods with River Access
Exterior

18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (60 reviews)
"Loved out stay! "
United States
Emilee
The price is HK$2,153
HK$3,109 total
includes taxes & fees
19 May - 20 May
18th Century Stone Cottage minutes from historic Middleburg
1 bedroom, WiFi, bed sheets

The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (47 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
The price is HK$970
HK$1,570 total
includes taxes & fees
25 May - 26 May
The Carriage House at Carrot Top Cottage
Exterior

Cottage on King | Charming Historic Leesburg Home

Cottage on King | Charming Historic Leesburg Home
Leesburg's Old and Historic District
9.6 out of 10, Exceptional, (70 reviews)
"Great location and very comfortable house. Beautiful place to stay, we loved sitting on the porch in the morning with coffee"
United States
Fern
The price is HK$1,585
HK$3,092 total
includes taxes & fees
20 May - 21 May
Cottage on King | Charming Historic Leesburg Home
Interior

Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (36 reviews)
"Great communication, very clean, beautiful views!"
United States
Lorie K.
The price is HK$783
HK$2,789 total
includes taxes & fees
20 May - 21 May
Antietam Look Out - Incredible Sunset Views!
Exterior

Lake View Retreat - Cottage Near a Peaceful Lake!

Lake View Retreat - Cottage Near a Peaceful Lake!
Harpers Ferry
9.6 out of 10, Exceptional, (22 reviews)
"The house had wonderful spaces to use for our weekend getaway!"
United States
Jessame P.
The price is HK$783
HK$2,700 total
includes taxes & fees
28 May - 29 May
Lake View Retreat - Cottage Near a Peaceful Lake!
Outdoor dining

Cozy cabin w/hot tub & game room

Cozy cabin w/hot tub & game room
Harpers Ferry
9.0 out of 10, Wonderful, (65 reviews)
"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"
United States
Chelsey-Ann
The price is HK$1,416
HK$2,688 total
includes taxes & fees
25 May - 26 May
Cozy cabin w/hot tub & game room
TV, fireplace

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Keedysville
9.8 out of 10, Exceptional, (67 reviews)
"Great home "
United States
January D.
The price is HK$971
HK$3,095 total
includes taxes & fees
1 Jun - 2 Jun
Sunny Streams Cabin - Sunset Views w/ a 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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Top Hillsboro Hotel Reviews

Best Western Leesburg Hotel & Conference Center

Best Western Leesburg Hotel & Conference Center

10/10 Excellent
"Great staff and accommodations for the evening."
Sharette 1-night trip
Posted 2 hours ago
Best Western Leesburg Hotel & Conference Center

Find out more about Hillsboro

Search for holiday rentals in Hillsboro on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillsboro using one of the methods below:

  • View our selection of featured holiday rentals in Hillsboro
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  • Enter your travel dates to view the best deals on holiday rentals in Hillsboro while they last

Look no further and take a look at our great range of rental properties in Hillsboro!

Frequently asked questions

Can I find holiday rentals in Hillsboro?

Yes, there are holiday rentals close to the most popular sights in Hillsboro, or you can select a more secluded option if you're looking for a relaxing stay.

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

Enchanting Cottage, walk to Downtown Harpers Ferry: This holiday home rental outside of Hillsboro is located in the city centre, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

What can I see and do in Hillsboro?

Explore the area and family-friendly sights such as John Brown Wax Museum, or get out into nature at a spot like Shenandoah Lake Beach. In the wider area, you’ll find Doukenie Winery and Breaux Vineyards.

What are holiday rentals like in Hillsboro?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Hillsboro. Holiday rentals offer amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for families.