Stephenson Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Stephenson holiday rentals

A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

1. Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Winchester Historic District
8.8 out of 10, Excellent, (5 reviews)
"The unit is very nice, exactly as described, The bed are comfortable and everything was fine. The location is excellent very near to historical sights and downtown shopping district."
United States
Timothy B.
The price is NZ$447
includes taxes & fees
19 Nov - 20 Nov
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A backyard patio with a stone-tiled floor, a wooden table with chairs, a barbecue grill, and a wooden fence.

2. Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.8 out of 10, Exceptional, (11 reviews)
"The property was exceptional and very comfortable. We enjoyed the amenities. We would book it for future trips again."
United States
Carolyn F.
The price is NZ$580
includes taxes & fees
15 Nov - 16 Nov
Cameron Charmer pristine downtown apt with double master suites
A modern apartment with a spiral staircase, a living area with a dark-colored sofa, a coffee table, and a kitchen in the background.

3. Executive Suites

Executive Suites
3.0 star property
Winchester
The price is NZ$518
includes taxes & fees
15 Nov - 16 Nov
Executive Suites
A hot tub in front of a wooden cabin with a tree in the background.

4. Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
Stephens City
10.0 out of 10, Exceptional, (15 reviews)
"This tiny house was an absolute dream to stay at! Jen is very attentive to detail- everything from the decor to the thoughtful welcome basket and supplying a feed bucket for the farm animals was perfection. My kids requested our next vacation just be there instead! "
United States
Laura H.
The price is NZ$315
includes taxes & fees
15 Dec - 16 Dec
Luxury tiny home farm stay on historic property with hot tub in Stephens City
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 living room with a sofa, coffee table, and lamps. There is a bookshelf and a framed picture on the wall.

6. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.0 out of 10, Wonderful, (22 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
The price is NZ$554
includes taxes & fees
15 Nov - 16 Nov
Nostalgia Lane in the heart of the city
A wooden deck with a ceiling fan, white door, and windows.

7. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (51 reviews)
"It was great and beautiful place to staying. Thanks for hospitality"
United States
Onon
The price is NZ$381
includes taxes & fees
22 Nov - 23 Nov
Mountain View Bungalow in Front Royal
A wooden deck with a glass enclosure, two chairs, and a view of trees.

8. 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, (112 reviews)
"Absolutely charming cabin - clean, comfortable and with lovely amenities."
United States
Diane S.
The price is NZ$534
includes taxes & fees
2 Dec - 3 Dec
Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake.
A hot tub with a wooden deck, a wooden cabin with large windows, and a deck chair.

9. Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly

Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
Gerrardstown
9.0 out of 10, Wonderful, (12 reviews)
"We had a fabulous time and highly recommend this rental."
United States
Amber H.
The price is NZ$615
includes taxes & fees
17 Nov - 18 Nov
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
A hot tub with a stone exterior wall, surrounded by trees and a red chair.

10. Stone chalet w/ views & hot tub

Stone chalet w/ views & hot tub
Gerrardstown
9.0 out of 10, Wonderful, (45 reviews)
"Lovely, cozy cabin. Hot tub was very relaxing. Overall a wonderful place to stay."
United States
Michael H.
The price is NZ$650
includes taxes & fees
7 Dec - 8 Dec
Stone chalet w/ views & hot tub
A hotel entrance with a sign, a wicker chair, a wooden lattice, and a white door.

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

Best location! The Pullman Apt @ historic 1799 Inn
Harpers Ferry
9.2 out of 10, Wonderful, (62 reviews)
"Location is unbeatable- but bring ear plugs for the train whistling through the night."
United States
Karla
The price is NZ$391
includes taxes & fees
15 Nov - 16 Nov
Best location! The Pullman Apt @ historic 1799 Inn
A forested campsite with Adirondack chairs, a fire pit, and a stone firewood stack.

12. Hidden Creekside retreat near 5 national parks, including Harpers Ferry

Hidden Creekside retreat near 5 national parks, including Harpers Ferry
Martinsburg
10.0 out of 10, Exceptional, (14 reviews)
"Wonderful location and property."
United States
Helen F.
The price is NZ$471
includes taxes & fees
15 Nov - 16 Nov
Hidden Creekside retreat near 5 national parks, including Harpers Ferry
A lakeside deck with red Adirondack chairs and a fire pit.

13. Log Cabin w/ Hot Tub & Waterfront Patio!

Log Cabin w/ Hot Tub & Waterfront Patio!
Harpers Ferry
9.6 out of 10, Exceptional, (32 reviews)
"Beautiful, well managed property. Quiet lake, rustic log cabin feel with modern amenities."
United States
Andrew A.
The price is NZ$807
includes taxes & fees
3 Dec - 4 Dec
Log Cabin w/ Hot Tub & Waterfront Patio!
A wooden staircase leading to a lofted area with a sign reading "Station" and a "Laundry" sign above a door.

14. Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Martinsburg
9.8 out of 10, Exceptional, (25 reviews)
"Nice place to stay. Could use some privacy."
United States
Arnold A.
The price is NZ$460
includes taxes & fees
18 Nov - 19 Nov
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
A cozy outdoor seating area with a sofa and a fire pit, wooden deck, and a glass door leading to an interior space.

15. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.6 out of 10, Exceptional, (14 reviews)
"Great place to stay to catch the northern entrance to Shenandoah. Comfortable beds, great furniture, and easy drive to Front Royal for dining. "
United States
Scott M.
The price is NZ$774
includes taxes & fees
24 Nov - 25 Nov
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
A wooden door leading into a room with a wooden floor, a small round table with a pink pot of flowers, and a window with curtains.

16. 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, (59 reviews)
"Great location, with some beautiful walks through town and to the rivers."
United States
Michael
The price is NZ$401
includes taxes & fees
15 Nov - 16 Nov
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
A wooden deck with a white railing, two Adirondack chairs, and a small table.

17. Secluded Cabin a Stone's Throw From the A.T.!

Secluded Cabin a Stone's Throw From the A.T.!
Harpers Ferry
10.0 out of 10, Exceptional, (48 reviews)
"We had a great stay!"
United States
Olivia T.
The price is NZ$898
includes taxes & fees
3 Dec - 4 Dec
Secluded Cabin a Stone's Throw From the A.T.!
A hot tub with a view of a forest and distant landscape.

18. Aslan's How - Cabin with Valley Views & Hot Tub!

Aslan's How - Cabin with Valley Views & Hot Tub!
Harpers Ferry
9.8 out of 10, Exceptional, (13 reviews)
"Overall, the cabin was very nice and provided a quiet getaway with relatively easy access to surrounding accommodations, including activities and restaurants."
United States
Tracy H.
The price is NZ$869
includes taxes & fees
19 Nov - 20 Nov
Aslan's How - Cabin with Valley Views & Hot Tub!
A modern house with a large window, a covered porch, and outdoor seating.

19. Chalet w/Hot Tub, Deck, Game Room & EV Charger

Chalet w/Hot Tub, Deck, Game Room & EV Charger
Stephens City
10.0 out of 10, Exceptional, (11 reviews)
"A wonderful place to relax and enjoy being with family or friends, with lots of room for the dogs to run and play!"
United States
Laura V.
The price is NZ$693
includes taxes & fees
30 Nov - 1 Dec
Chalet w/Hot Tub, Deck, Game Room & EV Charger
An outdoor deck with a sofa and chairs, wooden railings, and a view of a lake surrounded by trees.

20. 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 NZ$838
includes taxes & fees
3 Dec - 4 Dec
Cozy Cabin | Lakefront, Hot Tub, Outdoor Sauna
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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Find out more about Stephenson

Everything you need to know about Stephenson 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 Stephenson 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 Stephenson holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Stephenson holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stephenson. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stephenson 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 Stephenson holiday rentals we have selected for you start as low as NZ$304 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Stephenson rentals

At Expedia, we put the best Stephenson 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 Stephenson 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 Stephenson 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 Stephenson. 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 Stephenson?

Yes, there are holiday rentals in Stephenson close to Frederick County Fairgrounds, 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 Stephenson has to offer?

Blue Ridge Beauty Home Dog Friendly, Walk to Rivers, A.T. Trail, & HF. NEW LVP: This holiday home rental outside of Stephenson is located in the mountains, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Stephenson?

While exploring the area, visit family-friendly sights like Shenandoah Valley Discovery Museum, or get outside and enjoy nature at Jim Barnett Park. Other places in town to visit include Frederick County Fairgrounds and Red Bud Run.

What are holiday rentals like in Stephenson?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Stephenson. Holiday rentals offer extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.