Default HTG hotel image

Stephenson Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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.
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
9.8 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 AED 727
AED 1,290 total
includes taxes & fees
20 Oct - 21 Oct
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.
The price is AED 92
AED 911 total
includes taxes & fees
22 Oct - 23 Oct
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.
The price is AED 500
AED 1,186 total
includes taxes & fees
25 Oct - 26 Oct
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.
The price is AED 485
AED 863 total
includes taxes & fees
20 Oct - 21 Oct
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.
The price is AED 753
AED 1,373 total
includes taxes & fees
29 Oct - 30 Oct
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.
The price is AED 591
AED 1,248 total
includes taxes & fees
22 Oct - 23 Oct
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.
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.
The price is AED 680
AED 1,228 total
includes taxes & fees
29 Oct - 30 Oct
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.
The price is AED 731
AED 1,427 total
includes taxes & fees
9 Nov - 10 Nov
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.
The price is AED 853
AED 1,533 total
includes taxes & fees
9 Nov - 10 Nov
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.
The price is AED 367
AED 1,398 total
includes taxes & fees
21 Oct - 22 Oct
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.
The price is AED 367
AED 1,447 total
includes taxes & fees
28 Oct - 29 Oct
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)
The price is AED 311
AED 813 total
includes taxes & fees
21 Oct - 22 Oct
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.
The price is AED 496
AED 822 total
includes taxes & fees
21 Oct - 22 Oct
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.
The price is AED 397
AED 1,431 total
includes taxes & fees
3 Nov - 4 Nov
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, (111 reviews)
"It was very clean, comfortable and well supplied with everything you would need. Beautiful scenery."
United States
John B.
The price is AED 621
AED 1,336 total
includes taxes & fees
21 Oct - 22 Oct
~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.
The price is AED 367
AED 1,435 total
includes taxes & fees
21 Oct - 22 Oct
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.
The price is AED 389
AED 1,384 total
includes taxes & fees
26 Oct - 27 Oct
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.
The price is AED 549
AED 1,071 total
includes taxes & fees
21 Oct - 22 Oct
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Stephenson Hotel Reviews

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

8/10 Good
"Room was comfortable. Staff very helpful. Property was a bit shabby."
Michael 2-night trip
Posted 3 hours ago
Travelodge by Wyndham Winchester

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.