Hillsboro Holiday Rentals

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Our top choices for Hillsboro holiday rentals

❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.8 out of 10, Exceptional, (77 reviews)
"Cozy home, great location, and kind and helpful host. Would like to stay again. "
United States
Matthew S.
The price is AU$201
includes taxes & fees
29 June - 30 June
❤️ 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, (115 reviews)
"Good stay. Would visit again. "
United States
Lonnie F.
The price is AU$286
includes taxes & fees
11 June - 12 June
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (146 reviews)
"Love the place will book again"
United States
WAYNE M.
The price is AU$359
includes taxes & fees
7 June - 8 June
Charming "Cream of the Crop" Cape ~❤️of Middletown

~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, (90 reviews)
"The host had great communication and the place was exactly as pictured! "
United States
Colleen J.
The price is AU$509
includes taxes & fees
8 June - 9 June
~Family & Pet Friendly Mountain Retreat~ Steam Shower~ 5 minutes from lake.

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 AU$467
includes taxes & fees
7 June - 8 June
Antietam Creek - Quiet 2 Bedroom Cabin

Cabin at the Gap | You Won't Believe the View!

Cabin at the Gap | You Won't Believe the View!
Harpers Ferry
The price is AU$482
includes taxes & fees
8 June - 9 June
Cabin at the Gap | You Won't Believe the View!

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
9.8 out of 10, Exceptional, (201 reviews)
"We enjoyed our stay and the location was excellent"
United States
Barbara W.
The price is AU$248
includes taxes & fees
7 June - 8 June
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

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)
"Tim is a great host. The cottage was clean, comfortable and perfectly located. Perfect place to stay for a weekend getaway to Middleburg!"
United States
Alexander B.
The price is AU$551
includes taxes & fees
7 June - 8 June
18th Century Stone Cottage minutes from historic Middleburg

Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (37 reviews)
"Very welcoming, the house was way more than expected. My family and I didn't want to leave."
United States
Shanna B.
The price is AU$503
includes taxes & fees
9 June - 10 June
Antietam Look Out - Incredible Sunset Views!

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, (62 reviews)
"Host was welcoming and place was as described and in very clean condition. "
United States
Junaid B.
The price is AU$254
includes taxes & fees
11 June - 12 June
Cozy Getaway near Harper`s Ferry, C&O & Potomac

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (35 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 AU$428
includes taxes & fees
9 June - 10 June
Leesburg Hideaway- King Bed + Private Backyard

Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (23 reviews)
"Great view, very secluded"
United States
Matt s.
The price is AU$545
includes taxes & fees
22 June - 23 June
Cottage w/ Hot Tub and 100-Mile Valley Views!

Historic Getaway near C&O Canal, hiking and biking

Historic Getaway near C&O Canal, hiking and biking
Brunswick
9.8 out of 10, Exceptional, (6 reviews)
"Clean, great location, and charming/updated space. Highly recommend! Host was super communicative and helpful!! "
United States
Kaitlin L.
The price is AU$353
includes taxes & fees
7 June - 8 June
Historic Getaway near C&O Canal, hiking and biking

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, (64 reviews)
"The Host Heather have the most beautiful personality. She was very helpful. Told us the history of the home which we was able to appreciate everything about this beautiful home."
United States
Samira A.
The price is AU$359
includes taxes & fees
9 June - 10 June
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

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 AU$283
includes taxes & fees
7 June - 8 June
Beautiful, Historic, Hiking, Biking and C&O Canal

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 AU$596
includes taxes & fees
25 June - 26 June
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Near Loudoun Wine Trail: Apt w/ Restaurant On-site

Near Loudoun Wine Trail: Apt w/ Restaurant On-site
3.0 star property
Hamilton
The price is AU$494
includes taxes & fees
7 June - 8 June
Near Loudoun Wine Trail: Apt w/ Restaurant On-site

Forest chalet w/ hot tub & BBQ grill

Forest chalet w/ hot tub & BBQ grill
Harpers Ferry
9.2 out of 10, Wonderful, (33 reviews)
"Very nice cabin. Close to Harpers Ferry. Comfortable"
United States
Dianne A.
The price is AU$465
includes taxes & fees
28 June - 29 June
Forest chalet w/ hot tub & BBQ grill

Woodsy Retreat with a Hot Tub and Seasonal Views!

Woodsy Retreat with a Hot Tub and Seasonal Views!
Harpers Ferry
9.8 out of 10, Exceptional, (26 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
The price is AU$482
includes taxes & fees
8 June - 9 June
Woodsy Retreat with a Hot Tub and Seasonal Views!

super cosy cottage with high speed internet!

super cosy cottage with high speed internet!
Middleburg
9.4 out of 10, Exceptional, (14 reviews)
"Lovely setting in horse country with nice amenities "
United States
Christopher v.
The price is AU$457
includes taxes & fees
8 June - 9 June
super cosy cottage with high speed internet!
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

Everything you need to know about Hillsboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hillsboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hillsboro holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Hillsboro holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillsboro. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hillsboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hillsboro holiday rentals we have selected for you start as low as AU$201 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Hillsboro rentals

At Expedia, we put the best Hillsboro holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Hillsboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hillsboro holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hillsboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath: This holiday home rental outside of Hillsboro is located in the city centre, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Hillsboro?

Explore the area and family-friendly sights such as Hill High Country Store, 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.