Photo by Michael Kercsmar

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Hillsboro cottages

A modern building with large windows, a deck, and a stone wall.

1. 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, (29 reviews)
"Property was a great location for all we wanted to do during our vacation. The beach area was the perfect retreat for some relaxation after long days of hiking. Area is beautiful, house was comfortable (slept like a baby), and we had a great stay. Would definitely stay again."
United States
Rebecca N.
The price is NZ$872
includes taxes & fees
19 Nov - 20 Nov
Woodsy Retreat with a Hot Tub and Seasonal Views!
A wooden deck with a red umbrella, two chairs, and a table overlooking a calm lake surrounded by autumn foliage.

2. Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (29 reviews)
"With bedrooms and sitting rooms on 3 floors, our 3-generation family enjoyed having space to gather together as well as space for time apart. The decks allowed for additional places to enjoy the beautiful surroundings. Lake access was great for swimming and kayaking."
United States
Lindy K.
The price is NZ$992
includes taxes & fees
18 Nov - 19 Nov
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
A hot tub with a view of a forested landscape during sunset.

3. 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, (29 reviews)
"My husband and I went for a short trip. The communication was great and the house was perfect! We spent most of our time in the hot tub checking out the amazing view."
United States
Keri L.
The price is NZ$937
includes taxes & fees
23 Nov - 24 Nov
Cottage w/ Hot Tub and 100-Mile Valley Views!
A hot tub on a deck with a view of a lake and forest.

4. Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
9.8 out of 10, Exceptional, (42 reviews)
"The property was absolutely beautiful. The view of the lake was so pretty. Communication with the host was wonderful very informative. Very cozy and the house was beautiful inside."
United States
Tara G.
The price is NZ$954
includes taxes & fees
18 Nov - 19 Nov
Peaceful Lakefront Cottage with Mountain Views!
A spacious attic bedroom with a sloped ceiling, a large window, and a view of the outdoors.

5. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (27 reviews)
"Absolutely adorable, perfect location and well appointed. Would absolutely stay here again. Highly recommend and maybe if you’re lucky you’ll meet the little black cat who visited us!!"
United States
Abigail
The price is NZ$404
includes taxes & fees
16 Nov - 17 Nov
Quaint Mini Cottage in Shepherdstown - Walking Distance
A house with a stone foundation, a porch with a covered area, and a well-maintained lawn.

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

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
10.0 out of 10, Exceptional, (28 reviews)
"Fun place to stay!!!"
United States
Theresa R.
The price is NZ$671
includes taxes & fees
16 Nov - 17 Nov
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
A stone wall, a green house, a white door, and a table with chairs.

7. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (55 reviews)
"Very clean and convenient for seeing Harpers Ferry"
United States
Rich C.
The price is NZ$378
includes taxes & fees
16 Nov - 17 Nov
The Carriage House at Carrot Top Cottage
A patio with stone flooring, a round table, and metal chairs.

8. 18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg
Middleburg
10.0 out of 10, Exceptional, (68 reviews)
"A quaint cottage in a beautiful location!"
United States
Mary H.
The price is NZ$703
includes taxes & fees
16 Nov - 17 Nov
18th Century Stone Cottage minutes from historic Middleburg
A covered outdoor area with a concrete walkway, a parked car, and a grassy lawn with trees in the background.

9. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
3.0 star property
Shepherdstown
The price is NZ$643
includes taxes & fees
19 Nov - 20 Nov
Walk to Stores: Home in Historic Shepherdstown!
A two-story house with a covered porch and a wooden fence.

10. Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (36 reviews)
"We enjoyed our stay here so much and when we go back to Harper’s Ferry we hope to stay in the same place again"
United States
Zachary S.
The price is NZ$589
includes taxes & fees
18 Nov - 19 Nov
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
A two-story house with a porch and a front door.

11. Renovated 3B/3B Home | Downtown | Private Fire Pit

Renovated 3B/3B Home | Downtown | Private Fire Pit
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (44 reviews)
"Great location, would stay again."
United States
Eric D S.
The price is NZ$1,004
includes taxes & fees
16 Nov - 17 Nov
Renovated 3B/3B Home | Downtown | Private Fire Pit
A stone house with a white picket fence, a front porch, and potted plants.

12. Cottage w/ Furnished Patio & Garden: Dtwn Leesburg

Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (7 reviews)
"Great location to town of leesburg and can walk to restaurants and shops. Big kitchen and nice outdoor space. "
United States
Corky F.
The price is NZ$1,178
includes taxes & fees
22 Nov - 23 Nov
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
A hot tub under a wooden pergola with a grassy yard and trees in the background.

13. Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
9.4 out of 10, Exceptional, (40 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
United States
Felice N.
The price is NZ$978
includes taxes & fees
18 Nov - 19 Nov
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
A two-story house with a porch, a front door, and a number '190' sign.

14. Enchanting Victorian Cottage Just Steps From All the Major Sites in Harpers Ferry, WV

Enchanting Victorian Cottage Just Steps From All the Major Sites in Harpers Ferry, WV
Harpers Ferry
The price is NZ$980
includes taxes & fees
17 Nov - 18 Nov
Enchanting Victorian Cottage Just Steps From All the Major Sites in Harpers Ferry, WV
A view of a park with trees, a bridge, and a body of water.

15. Historic Stone Cottage with Hot Tub and Hammock, Minutes from Downtown Harpers Ferry, West Virginia

Historic Stone Cottage with Hot Tub and Hammock, Minutes from Downtown Harpers Ferry, West Virginia
Bolivar
The price is NZ$1,226
includes taxes & fees
1 Dec - 2 Dec
Historic Stone Cottage with Hot Tub and Hammock, Minutes from Downtown Harpers Ferry, West Virginia
A stone house with a white picket fence, a front porch, and potted plants.

16. Cottage w/ Furnished Patio & Garden: Dtwn Leesburg

Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
3.0 star property
Leesburg's Old and Historic District
The price is NZ$1,229
includes taxes & fees
22 Nov - 23 Nov
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
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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Learn more about Hillsboro

This tiny historic village charms visitors with its stone buildings and the Old Stone School's cultural events. Book a tasting at one of the nearby Loudoun County wineries or explore the quaint shops along Charles Town Pike.

See all hotels in Hillsboro
A stone building with a green roof and a covered patio area with outdoor seating.
Photo by Michael Kercsmar
Open Photo by Michael Kercsmar

Top reviews in Hillsboro

A hotel with a prominent "HOME" sign, outdoor seating area, and a covered entrance.
Home2 Suites by Hilton Charles Town

Home2 Suites by Hilton Charles Town

Home2 Suites by Hilton Charles Town
Charles Town

10/10 Excellent

Easy access to grocey shopping and plenty of options for eating out within no more than a 5 minute walk. The staff were amazing and helped us with every question we had.
Australia
Michael
Reviewed March 17, 2026
Home2 Suites by Hilton Charles Town

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