A wooden bridge over a gravel path, surrounded by trees and a stone wall, leading to a building with a spire.

Jefferson County Holiday Rentals

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Our top choices for Jefferson County holiday rentals

A living room with a dining table, chairs, a sofa, and a television.

1. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"Great location and home base for visiting Shepherdstown, Harpers Ferry, and Sharpsburg. Perfect for a couple."
United States
Virginia W.
The price is HK$942
HK$1,738 total
includes taxes & fees
18 Oct - 19 Oct
Quaint Mini Cottage in Shepherdstown - Walking Distance
A covered outdoor seating area with wicker furniture and a table, overlooking a parking lot and a building with a sign reading "1799 INN".

2. Best location! The Pullman Apt @ historic 1799 Inn

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.2 out of 10, Wonderful, (60 reviews)
"Location is unbeatable- but bring ear plugs for the train whistling through the night."
United States
Karla
The price is HK$1,065
HK$1,798 total
includes taxes & fees
15 Nov - 16 Nov
Best location! The Pullman Apt @ historic 1799 Inn
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

3. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (87 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
The price is HK$325
HK$838 total
includes taxes & fees
25 Oct - 26 Oct
❤️ Secluded 1940s Romantic Tiny House on the River
A spacious room with a large dining table, white chairs, and a ceiling fan.

4. Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake.

Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake.
Harpers Ferry
10.0 out of 10, Exceptional, (109 reviews)
"It was very clean, comfortable and well supplied with everything you would need. Beautiful scenery."
United States
John B.
The price is HK$1,507
HK$3,091 total
includes taxes & fees
9 Nov - 10 Nov
Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake.
A bedroom with a bed, a chair, a nightstand, a ceiling fan, and a window with curtains.

5. Schilling House

Schilling House
3.0 star property
Bolivar
The price is HK$2,150
HK$2,693 total
includes taxes & fees
19 Oct - 20 Oct
Schilling House
A wooden deck with two Adirondack chairs and a table overlooking a lake with trees and hills in the background.

6. Charming Cabin in the Woods with River Access

Charming Cabin in the Woods with River Access
Shepherdstown
9.6 out of 10, Exceptional, (55 reviews)
"Nice little place. Hosts were very responsive."
United States
Miki M.
The price is HK$1,157
HK$2,197 total
includes taxes & fees
12 Nov - 13 Nov
Charming Cabin in the Woods with River Access
A cozy living room with wooden walls, a flat-screen TV, a fireplace, and comfortable seating.

7. Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Harpers Ferry
9.2 out of 10, Wonderful, (55 reviews)
"Rental was exactly as advertised and in a great location within walking distance of a lot of great spots to check out."
United States
Sarah D.
The price is HK$1,138
HK$1,993 total
includes taxes & fees
25 Oct - 26 Oct
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

8. New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct

New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
Bolivar
9.8 out of 10, Exceptional, (50 reviews)
"Great location and incredibly well appointed!"
United States
Sarah M.
The price is HK$1,052
HK$2,282 total
includes taxes & fees
18 Oct - 19 Oct
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
A hot tub outside a building with a view of autumn trees.

9. 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 HK$785
HK$2,689 total
includes taxes & fees
21 Oct - 22 Oct
Woodsy Retreat with a Hot Tub and Seasonal Views!
A two-story house with a porch, green shutters, and a red roof.

10. Enchanting Cottage, walk to Downtown Harpers Ferry

Enchanting Cottage, walk to Downtown Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (58 reviews)
"Great place in historic Harper’s ferry. Only negative thing I can say is the parking is not ideal"
United States
Brett D.
The price is HK$1,613
HK$3,045 total
includes taxes & fees
21 Oct - 22 Oct
Enchanting Cottage, walk to Downtown Harpers Ferry
A modern kitchen with stainless steel appliances, a dining area with a round table, and a spiral staircase leading to a living area with a sofa and a coffee table.

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

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (34 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 HK$1,528
HK$2,664 total
includes taxes & fees
12 Nov - 13 Nov
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
A deck with outdoor seating and a lake view.

12. Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Harpers Ferry
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay and it was so nice for our dog as well. The Mountain Lake Cub had a doggy beach day on Saturday morning and it was a super fun experience. The host was friendly and responsive!"
United States
Dawn S.
The price is HK$314
HK$2,096 total
includes taxes & fees
22 Oct - 23 Oct
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
A bedroom with a bed, a table, and a view of the outdoors.

13. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (54 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
The price is HK$1,093
HK$1,724 total
includes taxes & fees
16 Nov - 17 Nov
The Carriage House at Carrot Top Cottage
A cylindrical metal building with a lit entrance, surrounded by trees.

14. Wild And Wonderful Silos

Wild And Wonderful Silos
Harpers Ferry
8.2 out of 10, Very good, (34 reviews)
"Cozy & Charming! Love the location! Really enjoyed our stay in the "Tiny House Silo!""
United States
Stephanie B.
The price is HK$1,530
HK$2,664 total
includes taxes & fees
3 Nov - 4 Nov
Wild And Wonderful Silos
A cozy cabin interior with a wooden interior, a sofa, a table, and a view through large windows.

15. Blue Ridge Getaway - Sunset Views, A.T. Access

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
9.8 out of 10, Exceptional, (78 reviews)
"Great stay! Wonderful property!"
United States
Thomas W.
The price is HK$895
HK$3,045 total
includes taxes & fees
26 Oct - 27 Oct
Blue Ridge Getaway - Sunset Views, A.T. Access
A covered outdoor area with wicker furniture, a ceiling fan, and a view of a lake and forest.

16. Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
9.8 out of 10, Exceptional, (42 reviews)
"Clean house. Host was able to accessible. Hot tub worked and clean. Kitchen had everything we needed. Great place to stay and relax"
United States
Lisa h.
The price is HK$902
HK$3,326 total
includes taxes & fees
4 Nov - 5 Nov
Peaceful Lakefront Cottage with Mountain Views!
A hot tub with a view of a forested landscape during sunset.

17. 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, (28 reviews)
"The property was so nice with a beautiful view. We had a great time! Highly recommend this property."
United States
Anonymous traveller
The price is HK$926
HK$3,189 total
includes taxes & fees
29 Oct - 30 Oct
Cottage w/ Hot Tub and 100-Mile Valley Views!
A wooden interior with a dining table set for four, a fireplace, and large windows offering a view of the outdoors.

18. Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna

Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
Harpers Ferry
9.8 out of 10, Exceptional, (49 reviews)
"Very relaxing great time."
United States
Alfred A.
The price is HK$1,051
HK$3,145 total
includes taxes & fees
4 Nov - 5 Nov
Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
A room with a large window overlooking a forested area.

19. Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Harpers Ferry
9.6 out of 10, Exceptional, (22 reviews)
"We had a wonderful stay. The communication and the guestbook were wonderful. The view was gorgeous and the property was clean and comfortable. "
United States
Kaitlyn C.
The price is HK$793
HK$3,101 total
includes taxes & fees
28 Oct - 29 Oct
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
A forested area with a metal railing and a paved path.

20. Mountain Cabin in the Woods, Near Wineries & More!

Mountain Cabin in the Woods, Near Wineries & More!
Harpers Ferry
8.8 out of 10, Excellent, (36 reviews)
"House was cute with a great location! Very comfortable and host was very responsive!"
United States
Lisa P.
The price is HK$1,109
HK$1,950 total
includes taxes & fees
19 Oct - 20 Oct
Mountain Cabin in the Woods, Near Wineries & More!
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 Jefferson County Hotel Reviews

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent
"Loved our stay, it was well priced and had everything we needed!"
Christopher 1-night trip
Posted 6 hours ago
Microtel Inn & Suites by Wyndham Winchester