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Stephenson Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

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
10.0 out of 10, Exceptional, (2 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 AU$364
includes taxes & fees
8 Sept - 9 Sept
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, (9 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 AU$486
includes taxes & fees
13 Sept - 14 Sept
Cameron Charmer pristine downtown apt with double master suites
A modern living room with a fireplace, a round coffee table, and a comfortable seating area.

3. Indigo Blue modern open vibe on tree lined street

Indigo Blue modern open vibe on tree lined street
Winchester Historic District
9.8 out of 10, Exceptional, (15 reviews)
"We had a great stay! The place was very clean and exactly as described. Michele communicated clearly and responded quickly, which made everything easy from check-in to check-out. The location was also perfect—very close to downtown and convenient to everything we wanted to do. We would definitely stay here again and highly recommend it to others!"
United States
Elaina R.
The price is AU$625
includes taxes & fees
12 Sept - 13 Sept
Indigo Blue modern open vibe on tree lined street

4. Stone chalet w/ views & hot tub

Stone chalet w/ views & hot tub
Gerrardstown
9.0 out of 10, Wonderful, (43 reviews)
"Lovely, cozy cabin. Hot tub was very relaxing. Overall a wonderful place to stay."
United States
Michael H.
The price is AU$414
includes taxes & fees
21 Sept - 22 Sept
Stone chalet w/ views & hot tub
A spacious living area with a stone wall, a fireplace, a blue sofa, and a kitchen with wooden cabinets and a large window.

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

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Gerrardstown
7.8 out of 10, Good, (20 reviews)
"Nice relaxing place. Enjoyed it very much."
United States
Scott K.
The price is AU$431
includes taxes & fees
13 Sept - 14 Sept
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin

6. 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 AU$457
includes taxes & fees
8 Sept - 9 Sept
Forest 2BR chalet w/ hot tub & backyard
A bedroom with a bed, two windows, a ceiling fan, a green armchair, a dresser, and a nightstand with a lamp.

7. 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 AU$452
includes taxes & fees
30 Sept - 1 Oct
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly
A hot tub outside a building with a view of autumn trees.

8. 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, (26 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
The price is AU$474
includes taxes & fees
8 Sept - 9 Sept
Woodsy Retreat with a Hot Tub and Seasonal Views!
A hot tub in front of a wooden cabin with a tree in the background.

9. 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, (13 reviews)
"The house was wonderfully situated and stocked for our needs. It is very well kept and decorated. We enjoyed our stay very much!"
United States
Shawn P.
The price is AU$258
includes taxes & fees
13 Sept - 14 Sept
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A deck with outdoor seating and a lake view.

10. 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
9.8 out of 10, Exceptional, (9 reviews)
"Had a wonderful stay here. Shaun was an excellent host with easy communication. Peaceful location with a lake! Convenient to Harper’s Ferry. "
United States
Liz P.
The price is AU$334
includes taxes & fees
13 Sept - 14 Sept
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
A rustic cabin interior with a leather sofa, wooden beams, and mounted animal heads.

11. Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.

Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.
Cross Junction
9.6 out of 10, Exceptional, (87 reviews)
Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.
A living room with a dining table, chairs, a sofa, and a television.

12. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (24 reviews)
"Host let us in a bit early which was nice!"
United States
John
The price is AU$309
includes taxes & fees
8 Sept - 9 Sept
Quaint Mini Cottage in Shepherdstown - Walking Distance
A modern building with a patio area, a fire pit, and a view of a river and forest.

13. Cabin at the Gap | You Won't Believe the View!

Cabin at the Gap | You Won't Believe the View!
Harpers Ferry
10.0 out of 10, Exceptional, (1 review)
"Great views, house is clean and cozy with a fireplace"
United States
Matthew P.
The price is AU$474
includes taxes & fees
9 Sept - 10 Sept
Cabin at the Gap | You Won't Believe the View!
A hot tub in a forested area with a rocky ground and trees.

14. The Blue Jay | New House in the Woods w/ Hot Tub

The Blue Jay | New House in the Woods w/ Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (5 reviews)
"Great place. Very well stocked house everything you need Great response from host. Very nice place. Road is a little rough as explained in listing "
United States
Brett D.
The price is AU$509
includes taxes & fees
10 Sept - 11 Sept
The Blue Jay | New House in the Woods w/ Hot Tub
A spacious room with a large dining table, white chairs, and a ceiling fan.

15. 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, (103 reviews)
"Great property, host was very communicative!"
United States
Lizzy H.
The price is AU$504
includes taxes & fees
8 Sept - 9 Sept
Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!
A cozy cabin interior with a wooden interior, a sofa, a table, and a view through large windows.

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

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
9.8 out of 10, Exceptional, (76 reviews)
"This was an absolutely amazing stay. Beautiful location, extremely comfortable. Well stocked kitchen. Wonderful hot tub. Perfection for a getaway."
United States
Andrew L.
The price is AU$509
includes taxes & fees
10 Sept - 11 Sept
Blue Ridge Getaway - Sunset Views, A.T. Access
A room with a large window overlooking a forested area.

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

Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (20 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 AU$540
includes taxes & fees
8 Sept - 9 Sept
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
A hot tub with a view of a forested landscape during sunset.

18. 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, (26 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 AU$521
includes taxes & fees
14 Sept - 15 Sept
Cottage w/ Hot Tub and 100-Mile Valley Views!
A wooden deck with two Adirondack chairs and a small table, two wine glasses on the table, surrounded by lush green trees.

19. 4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
Harpers Ferry
9.6 out of 10, Exceptional, (9 reviews)
"House was beautiful and fully equipped for our stay. The host was very communicative and we really enjoyed our time here. If in the area again would definitely stay here. "
United States
Maeve K.
The price is AU$594
includes taxes & fees
22 Sept - 23 Sept
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
A hot tub on a wooden deck with an American flag, string lights, and a view of the landscape.

20. Large Glamper w/ Hot Tub and full bathroom-sleep 6

Large Glamper w/ Hot Tub and full bathroom-sleep 6
Capon Bridge
9.8 out of 10, Exceptional, (25 reviews)
"I can't express enough how appreciative we are to the owner and manager. Best time I've had in years. "
United States
Mary
The price is AU$333
includes taxes & fees
15 Sept - 16 Sept
Large Glamper w/ Hot Tub and full bathroom-sleep 6
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

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"It was fine"
Rodney 1-night trip
Posted 1 hour ago
Holiday Inn Winchester Se-Historic Gateway by IHG

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 favourite 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 depend 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 per night. Entering your travel dates in the search wizard might find you 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?

Mountain View Bungalow in Front Royal: This holiday home rental outside of Stephenson offers a garden, a selection of games and air conditioning to help you feel perfectly comfortable 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 Mackintosh Fruit Farm. 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.