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Stephenson Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Stephenson vacation 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.
$232 nightly
The price is $263
Oct 19 - Oct 20
Total with taxes and fees
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A two-story house with a front porch, a mailbox, and a number plate.

2. Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.6 out of 10, Exceptional, (10 reviews)
"The property was exceptional and very comfortable. We enjoyed the amenities. We would book it for future trips again."
United States
Carolyn F.
$310 nightly
The price is $351
Oct 19 - Oct 20
Total with taxes and fees
Cameron Charmer pristine downtown apt with double master suites
A deck with outdoor seating and a lake view.

3. 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, (13 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.
$234 nightly
The price is $260
Oct 22 - Oct 23
Total with taxes and fees
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
A spacious living area with a stone wall, a fireplace, a blue sofa, and a kitchen with wooden cabinets and a large window.

4. Fireplace, Wraparound Deck, & WiFi at Chalet Cabin

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Gerrardstown
7.8 out of 10, Good, (24 reviews)
"Nice relaxing place. Enjoyed it very much."
United States
Scott K.
$299 nightly
The price is $323
Oct 25 - Oct 26
Total with taxes and fees
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
A living room with a dining table, chairs, a sofa, and a television.

5. 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.
$211 nightly
The price is $235
Oct 20 - Oct 21
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
A dining area with a white table and bench, a hanging light fixture, and a door leading to another room.

6. WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Old Town Winchester
9.0 out of 10, Wonderful, (10 reviews)
"Great location…"
United States
John P.
$330 nightly
The price is $374
Oct 19 - Oct 20
Total with taxes and fees
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Forest Haven is beautiful at night

7. Forest 2BR chalet w/ hot tub & backyard

Forest 2BR chalet w/ hot tub & backyard
Gerrardstown
9.6 out of 10, Exceptional, (5 reviews)
"Just an overnight stay. On our way back home from northern New York. The place was nice. It is peaceful sitting on the deck. The check in process was a little tedious with various emails and downloads required. The Backstep is a little sketchy. Be careful walking in. Overall the place was nice"
United States
John Z.
$305 nightly
The price is $340
Oct 22 - Oct 23
Total with taxes and fees
Forest 2BR chalet w/ hot tub & backyard
A house with a well-lit entrance, a small garden, and a gravel driveway.

8. 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, (24 reviews)
"Nice place to stay. Could use some privacy."
United States
Arnold A.
$235 nightly
The price is $261
Oct 20 - Oct 21
Total with taxes and fees
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
A living room with a sofa, armchair, coffee table, and a television.

9. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
8.8 out of 10, Excellent, (21 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
$295 nightly
The price is $334
Oct 19 - Oct 20
Total with taxes and fees
Nostalgia Lane in the heart of the city
Grab a towel and relax in the hot tub

10. Stone chalet w/ views & hot tub

Stone chalet w/ views & hot tub
Gerrardstown
9.0 out of 10, Wonderful, (44 reviews)
"Lovely, cozy cabin. Hot tub was very relaxing. Overall a wonderful place to stay."
United States
Michael H.
$353 nightly
The price is $382
Oct 19 - Oct 20
Total with taxes and fees
Stone chalet w/ views & hot tub
A living room with a TV, two sofas, a coffee table, and a large plant.

11. 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.
$385 nightly
The price is $417
Nov 9 - Nov 10
Total with taxes and fees
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
A spacious living area with a fireplace, a sofa, and a coffee table.

12. 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.
$342 nightly
The price is $381
Oct 21 - Oct 22
Total with taxes and fees
Aslan's How - Cabin with Valley Views & Hot Tub!
A room with a large window overlooking a forested area.

13. 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.
$354 nightly
The price is $394
Oct 28 - Oct 29
Total with taxes and fees
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
A natural setting with a body of water, trees, and a sandy area.

14. Fox Burrow @ Timber Ridge Retreat

Fox Burrow @ Timber Ridge Retreat
Berkeley Springs
10.0 out of 10, Exceptional, (2 reviews)
$210 nightly
The price is $221
Oct 19 - Oct 20
Total with taxes and fees
Fox Burrow @ Timber Ridge Retreat
A wooden deck with white railings and a covered porch area.

15. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (46 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
$201 nightly
The price is $224
Oct 21 - Oct 22
Total with taxes and fees
Mountain View Bungalow in Front Royal
A cabin with a stone fire pit and white Adirondack chairs, surrounded by trees and a view of the sunset.

16. Rebels Rest - Cabin with Enchanting Sunset Views!

Rebels Rest - Cabin with Enchanting Sunset Views!
Harpers Ferry
9.8 out of 10, Exceptional, (42 reviews)
"Enjoyed our visit. House was well-appointed and had an amazing view from back deck."
United States
Kathy V.
$350 nightly
The price is $390
Nov 3 - Nov 4
Total with taxes and fees
Rebels Rest - Cabin with Enchanting Sunset Views!
A spacious room with a large dining table, white chairs, and a ceiling fan.

17. ~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.
$327 nightly
The price is $364
Oct 21 - Oct 22
Total with taxes and fees
~Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake
A spacious living area with a high ceiling, a fireplace, and a kitchen in the background.

18. 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, (46 reviews)
"We had a great stay!"
United States
Olivia T.
$351 nightly
The price is $391
Oct 21 - Oct 22
Total with taxes and fees
Secluded Cabin a Stone's Throw From the A.T.!
A cozy cabin interior with a wooden interior, a sofa, a table, and a view through large windows.

19. 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.
$338 nightly
The price is $376
Oct 26 - Oct 27
Total with taxes and fees
Blue Ridge Getaway - Sunset Views, A.T. Access
A hot tub on a wooden deck with a red umbrella, surrounded by greenery and a clear sky.

20. Modern w Mountain Views, Hot Tub, Deck & Fire Pit

Modern w Mountain Views, Hot Tub, Deck & Fire Pit
Berkeley Springs
9.4 out of 10, Exceptional, (15 reviews)
"Beautiful get away"
United States
Brett R.
$271 nightly
The price is $292
Oct 19 - Oct 20
Total with taxes and fees
Modern w Mountain Views, Hot Tub, Deck & Fire Pit
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 Stephenson Hotel Reviews

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Location is excellent. Walking distance to restaurants, coffee shops and bars as well as historical sites. Staff is always excellent, neatly dressed, well spoken and professional. The property is an architectural gem. The lobby, bar and general interior details like the interior woodwork, floors, elevators and mail chutes are remarkable. Best shower ever! Go to Knead Bread for breakfast. It would be a standout in any major city."
Paul 1-night trip
Posted 17 hours ago
The George Washington Hotel, A Wyndham Grand Hotel

Find out more about Stephenson

Everything you need to know about Stephenson vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Stephenson vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Stephenson vacation 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 low season months. For more hustle and bustle, you may prefer to visit Stephenson in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $218 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Stephenson rentals

At Expedia, we put the best Stephenson vacation 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 vacation.

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 vacation rentals in Stephenson?

Yes, we have vacation rentals in Stephenson close to Frederick County Fairgrounds, or you can go with a secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Stephenson?

Blue Ridge Beauty Home Dog Friendly, Walk to Rivers, A.T. Trail, & HF. NEW LVP: Visitors like this Stephenson vacation home rental. It is located in the mountains and has a patio, a barbecue grill, 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 vacation rentals like in Stephenson?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Stephenson. Vacation rentals offer extras such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family gatherings.