Default HTG hotel image

Stephenson Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Stephenson holiday rentals

1. Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
8.8 out of 10, Excellent, (10 reviews)
"This property was the perfect stop for our overnight stay in Winchester. The perfect, quiet neighborhood very close to the walking mall. Just what we needed. "
United States
Anonymous traveller
Cozy English Basement Apt quiet but close to downtown

2. Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.6 out of 10, Exceptional, (9 reviews)
"This was yhe perfect place for us to stay in Old Winchester. A short walk to just about everything. The apartment was clean and comfortable. We had no issues with checking in and communication was great with the property owner. We would definitely rent from them again."
United States
Stephanie L.
The price is NZ$365
includes taxes & fees
9 Sept - 10 Sept
Pretty Little Apt by the Train II

3. 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 NZ$631
includes taxes & fees
9 Sept - 10 Sept
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

4. Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.8 out of 10, Exceptional, (7 reviews)
"amazing location, felt like home, lots of space!"
United States
Brandi M.
The price is NZ$663
includes taxes & fees
9 Sept - 10 Sept
Scarborough Fair walk to downtown two story apt

5. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.2 out of 10, Wonderful, (18 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$565
includes taxes & fees
9 Sept - 10 Sept
Nostalgia Lane in the heart of the city

6. 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 NZ$544
includes taxes & fees
19 Aug - 20 Aug
Stone chalet w/ views & hot tub

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

Fireplace, Wraparound Deck, & WiFi at Chalet Cabin
Gerrardstown
8.2 out of 10, Very good, (19 reviews)
"Nice relaxing place. Enjoyed it very much."
United States
Scott K.
The price is NZ$519
includes taxes & fees
23 Aug - 24 Aug
Fireplace, Wraparound Deck, & WiFi at Chalet Cabin

8. 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$521
includes taxes & fees
25 Aug - 26 Aug
Hot Tub, Fire Pit, Deck, Grill, WiFi, Dog-Friendly

9. 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 NZ$564
includes taxes & fees
9 Sept - 10 Sept
Forest 2BR chalet w/ hot tub & backyard

10. Peaceful mountain cabin in charming Berryville VA - next to river and brewery

Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Berryville
10.0 out of 10, Exceptional, (1 review)
"Loved the place, the log cabin has the old world charm and beautiful settings. "
United States
Anonymous traveller
The price is NZ$408
includes taxes & fees
19 Aug - 20 Aug
Peaceful mountain cabin in charming Berryville VA - next to river and brewery

11. 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, (11 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 NZ$312
includes taxes & fees
31 Aug - 1 Sept
Luxury tiny home farm stay on historic property with hot tub in Stephens City

12. 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, (84 reviews)
"The best, peaceful, fun, ATV wheeling, target practice, grilling, great kitchen supplies and plenty of space for the family Would stay again"
United States
Lisa G.
The price is NZ$543
includes taxes & fees
16 Aug - 17 Aug
Historic pet friendly cabin with shooting range, and ATV trails on 80 acres.

13. 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)
"We enjoyed our stay and the property was exactly what we were looking for in a mountain getaway peaceful, private, and immersed in the woods with beautiful views and a relaxing atmosphere.The home was clean, quiet, and met our needs well for a restful escape. The hosts were communicative and supportive, although we did not need to reach out during our stay.The driveway is definitely mountain-style, so guests should come prepared and be mindful of the vehicle they bring, but the secluded setting...
United States
B S.
The price is NZ$650
includes taxes & fees
19 Aug - 20 Aug
Cottage w/ Hot Tub and 100-Mile Valley Views!

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

Blue Ridge Getaway - Sunset Views, A.T. Access
Harpers Ferry
9.8 out of 10, Exceptional, (75 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 NZ$609
includes taxes & fees
12 Aug - 13 Aug
Blue Ridge Getaway - Sunset Views, A.T. Access

15. New 4br Townhome Near Harpers Ferry 4 Bedroom Townhouse

New 4br Townhome Near Harpers Ferry 4 Bedroom Townhouse
3.0 star property
Charles Town
The price is NZ$738
includes taxes & fees
12 Aug - 13 Aug
New 4br Townhome Near Harpers Ferry 4 Bedroom Townhouse

16. 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, (99 reviews)
"Great property, host was very communicative!"
United States
Lizzy H.
The price is NZ$627
includes taxes & fees
24 Aug - 25 Aug
Family & Pet Friendly Mountain Cabin~ Steam Shower~ 5 minutes from lake!

17. Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (40 reviews)
"Beautiful, relaxing and quiet cabin, exceeded expectations."
United States
Johnathan B.
The price is NZ$401
includes taxes & fees
13 Aug - 14 Aug
Blue Mountain Cabin, secluded, perfect for couples, near main road

18. Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
10.0 out of 10, Exceptional, (36 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
United States
Felice N.
The price is NZ$1,273
includes taxes & fees
3 Sept - 4 Sept
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

19. Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.0 out of 10, Wonderful, (10 reviews)
"Stayed here with my 5 month old daughter, my mom and a friend and we had a blast. Kind folks, beautiful grounds and a super cute barn apartment! The fresh flowers in the kitchen were a lovely touch. "
United States
Haley M.
The price is NZ$365
includes taxes & fees
17 Aug - 18 Aug
Lunar Loft, with mountain views

20. Bluemont home just minutes to wineries, breweries, hiking and more!

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
10.0 out of 10, Exceptional, (1 review)
"Amazingly comfortable place to call home for a few days with plenty of room for activities if you have to stay in! Bedrooms were lovely as were the bathrooms. Updated and very clean!!!! Host was extremely responsive and very easy to work with!! Bonus to bring our pup with us for the stay."
United States
K O.
The price is NZ$576
includes taxes & fees
13 Aug - 14 Aug
Bluemont home just minutes to wineries, breweries, hiking and 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Stephenson Hotel Reviews

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$372 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?

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 Dinosaur Land, 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.