Hillsboro Vacation Rentals

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Our top choices for Hillsboro vacation rentals

❤️ 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 CA $89
CA $183 total
includes taxes & fees
Jun 1 - Jun 2
❤️ Secluded 1940s Romantic Tiny House on the River

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 CA $103
CA $275 total
includes taxes & fees
May 19 - May 20
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

~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 CA $230
CA $501 total
includes taxes & fees
May 19 - May 20
~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake!

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 CA $117
CA $334 total
includes taxes & fees
May 20 - May 21
Charming "Cream of the Crop" Cape ~❤️of Middletown

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 CA $309
CA $544 total
includes taxes & fees
May 19 - May 20
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

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 CA $275
CA $459 total
includes taxes & fees
May 19 - May 20
Antietam Creek - Quiet 2 Bedroom Cabin

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 CA $186
CA $424 total
includes taxes & fees
May 20 - May 21
Leesburg Hideaway- King Bed + Private Backyard

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 CA $199
CA $242 total
includes taxes & fees
May 19 - May 20
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

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 CA $266
CA $461 total
includes taxes & fees
May 21 - May 22
Secluded cabin w/hot tub & deck, dog-friendly

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 CA $159
CA $276 total
includes taxes & fees
May 20 - May 21
Beautiful, Historic, Hiking, Biking and C&O Canal

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 CA $186
CA $417 total
includes taxes & fees
May 25 - May 26
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

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 CA $136
CA $248 total
includes taxes & fees
May 20 - May 21
Cozy Getaway near Harper`s Ferry, C&O & Potomac

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 CA $264
CA $467 total
includes taxes & fees
May 25 - May 26
Charming Cabin in the Woods with River Access

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 CA $378
CA $543 total
includes taxes & fees
Jun 7 - Jun 8
18th Century Stone Cottage minutes from historic Middleburg

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 CA $170
CA $279 total
includes taxes & fees
May 19 - May 20
The Carriage House at Carrot Top Cottage

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 CA $280
CA $546 total
includes taxes & fees
May 20 - May 21
Cottage on King | Charming Historic Leesburg Home

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 CA $138
CA $494 total
includes taxes & fees
May 20 - May 21
Antietam Look Out - Incredible Sunset Views!

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 CA $138
CA $502 total
includes taxes & fees
May 25 - May 26
Lake View Retreat - Cottage Near a Peaceful Lake!

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 CA $249
CA $476 total
includes taxes & fees
May 25 - May 26
Cozy cabin w/hot tub & game room

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 CA $168
CA $552 total
includes taxes & fees
Jun 1 - Jun 2
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

Find out more about Hillsboro

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Hillsboro. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Hillsboro?

Yes, there are vacation rentals near popular points of interest in Hillsboro, or you can choose a secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Hillsboro?

Enchanting Cottage, walk to Downtown Harpers Ferry: Visitors like this Hillsboro vacation home rental. It is located in the city center 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 larger area, you’ll find Doukenie Winery and Breaux Vineyards.

What are vacation rentals like in Hillsboro?

Vacation rentals are private accommodations you can stay in for a few days or a quick weekend in Hillsboro. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family trip or a small group gathering.