A mountainous landscape with autumn foliage.

Stephens City Holiday Rentals

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Our top choices for Stephens City holiday rentals

1. 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
9.8 out of 10, Exceptional, (10 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$264
includes taxes & fees
12 Aug - 13 Aug
Luxury tiny home farm stay on historic property with hot tub in Stephens City

2. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (34 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is AU$321
includes taxes & fees
4 Aug - 5 Aug
Mountain View Bungalow in Front Royal

3. Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
9.6 out of 10, Exceptional, (8 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
The price is AU$253
includes taxes & fees
9 Aug - 10 Aug
Cozy English Basement Apt quiet but close to downtown

4. 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, (1 review)
"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$373
includes taxes & fees
3 Aug - 4 Aug
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

5. Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is AU$428
includes taxes & fees
2 Aug - 3 Aug
Morocco Loft 2BR overlooking city walking mall

6. The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.6 out of 10, Good, (8 reviews)
"If you want to be in the town and have quick access to everything, this is the place for you."
United States
Chris C.
The price is AU$449
includes taxes & fees
6 Aug - 7 Aug
The Queen of Winchester Three Bedroom with Upper Level Deck

7. 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 AU$315
includes taxes & fees
30 Aug - 31 Aug
Pretty Little Apt by the Train II

8. Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Winchester Historic District
8.8 out of 10, Excellent, (5 reviews)
"Loved being so close to the old town; was able to walk to a lot of places. Great to have an assigned parking spot in a lot behind the building. Enjoyed staying here a lot!"
United States
Leslie L.
The price is AU$338
includes taxes & fees
31 Aug - 1 Sept
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

9. 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)
"Nice house in a good central location. "
United States
Mitchell V.
The price is AU$493
includes taxes & fees
2 Aug - 3 Aug
Cameron Charmer pristine downtown apt with double master suites

10. Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.0 out of 10, Very good, (2 reviews)
"Small but appropriately priced."
United States
John M.
The price is AU$277
includes taxes & fees
25 Aug - 26 Aug
Rosamond nice downtown studio apt

11. The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
Winchester Historic District
7.0 out of 10, Good, (2 reviews)
"Everything went smoothly. Easy stay. Clean. Small efficiency with futon for bed."
United States
Greg A.
The price is AU$285
includes taxes & fees
16 Aug - 17 Aug
The Stock Exchange downtown 3rd floor studio apt

12. 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, (5 reviews)
The price is AU$607
includes taxes & fees
17 Aug - 18 Aug
Chalet w/Hot Tub, Deck, Game Room & EV Charger

13. Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Old Town Winchester
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is AU$360
includes taxes & fees
31 Aug - 1 Sept
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

14. 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, (17 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 AU$471
includes taxes & fees
2 Aug - 3 Aug
Nostalgia Lane in the heart of the city

15. Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Front Royal
9.8 out of 10, Exceptional, (15 reviews)
"Unique and adorable little place on the river. Perfectly clean and comfortable. We would definitely book again!"
United States
Hailey
The price is AU$608
includes taxes & fees
4 Aug - 5 Aug
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

16. 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 AU$550
includes taxes & fees
2 Aug - 3 Aug
Scarborough Fair walk to downtown two story apt

17. Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything

Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Old Town Winchester
The price is AU$486
includes taxes & fees
31 Aug - 1 Sept
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything

18. 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 AU$523
includes taxes & fees
16 Aug - 17 Aug
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

19. Bend of Brothers’ | Riverfront Cottage Shenandoah

Bend of Brothers’ | Riverfront Cottage Shenandoah
Front Royal
8.0 out of 10, Very good, (1 review)
"This is a new place and owners have done great work . Excellent value for the money ."
United States
Dave B.
The price is AU$681
includes taxes & fees
2 Aug - 3 Aug
Bend of Brothers’ | Riverfront Cottage Shenandoah

20. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (48 reviews)
"What an absolutely lovely and peaceful place to stay! We had a wonderful visit. "
United States
Stephanie T.
The price is AU$436
includes taxes & fees
9 Aug - 10 Aug
Newly renovated Farm cottage with Mountain views
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 Stephens City Hotel Reviews

Find out more about Stephens City

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

Stephens City holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stephens City. 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 Stephens City 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 Stephens City holiday rentals we have selected for you start as low as AU$321 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Stephens City rentals

At Expedia, we put the best Stephens City 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 Stephens City 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 Stephens City 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 Stephens City. 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

Are there holiday rentals in Stephens City?

Yes, there are holiday rentals in Stephens City close to Appleland Sports Center, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Stephens City has a good selection of restaurants. Make sure you have time to check out the shopping and wineries during your trip.

What are some of the best holiday rentals that Stephens City has to offer?

Cozy Lakeside Homestead: This holiday home rental outside of Stephens City is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Stephens City?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Stephens City stay.

What’s there to see and do in Stephens City?

While exploring the area, visit family-friendly sights like Appleland Sports Center, or get outside and enjoy nature at Lake Frederick Boat Launch. In the wider area, you’ll find Valerie Hill Winery and Dinosaur Land.

What’s a holiday rental in Stephens City like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Stephens City. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for small groups.