A mountainous landscape with autumn foliage.

Stephens City Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Stephens City vacation rentals

Terrace/patio

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
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.
$166 nightly
The price is $185
Aug 24 - Aug 25
Total with taxes and fees
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Terrace/patio

2. 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 traveler
$155 nightly
The price is $176
Aug 17 - Aug 18
Total with taxes and fees
Cozy English Basement Apt quiet but close to downtown
Terrace/patio

3. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (35 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
$199 nightly
The price is $221
Aug 18 - Aug 19
Total with taxes and fees
Mountain View Bungalow in Front Royal
Interior

4. 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.
$172 nightly
The price is $195
Aug 25 - Aug 26
Total with taxes and fees
Rosamond nice downtown studio apt
Outdoor dining

5. 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, (6 reviews)
$335 nightly
The price is $367
Sep 1 - Sep 2
Total with taxes and fees
Chalet w/Hot Tub, Deck, Game Room & EV Charger
TV

6. 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.
$232 nightly
The price is $263
Aug 17 - Aug 18
Total with taxes and fees
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
Exterior detail

7. 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.
$177 nightly
The price is $201
Aug 25 - Aug 26
Total with taxes and fees
The Stock Exchange downtown 3rd floor studio apt
Fridge, microwave, oven, stovetop

8. 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.
$267 nightly
The price is $279
Aug 19 - Aug 20
Total with taxes and fees
The Queen of Winchester Three Bedroom with Upper Level Deck
Interior

9. 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)
"It was decorated very cute and the bed was comfortable. Very close to shops and restaurants.We had to drive around the block and get out to find the location because you park and enter through the back door.It’s very close to the train stain but was only interrupted by an early morning train once."
United States
Brenda H.
$194 nightly
The price is $220
Aug 30 - Aug 31
Total with taxes and fees
Pretty Little Apt by the Train II
Smart TV, books

10. 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
8.4 out of 10, Very Good, (6 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.
$209 nightly
The price is $237
Aug 31 - Sep 1
Total with taxes and fees
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Smart TV

11. Yellow Submarine trendy basement apt and courtyard

Yellow Submarine trendy basement apt and courtyard
Old Town Winchester
7.6 out of 10, Good, (4 reviews)
"You need to add some kitchen tongs Otherwise everything was fantastic!!!"
United States
Michelle K.
$230 nightly
The price is $261
Aug 17 - Aug 18
Total with taxes and fees
Yellow Submarine trendy basement apt and courtyard
Exterior

12. 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.
$312 nightly
The price is $354
Aug 17 - Aug 18
Total with taxes and fees
Cameron Charmer pristine downtown apt with double master suites
Smart TV

13. 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.
$297 nightly
The price is $337
Aug 17 - Aug 18
Total with taxes and fees
Nostalgia Lane in the heart of the city
Private kitchen

14. 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.
$223 nightly
The price is $253
Aug 31 - Sep 1
Total with taxes and fees
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
Interior

15. Indigo Blue modern open vibe on tree lined street

Indigo Blue modern open vibe on tree lined street
Winchester Historic District
10.0 out of 10, Exceptional, (14 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.
$360 nightly
The price is $408
Aug 23 - Aug 24
Total with taxes and fees
Indigo Blue modern open vibe on tree lined street
Dining

16. 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.
$332 nightly
The price is $376
Aug 17 - Aug 18
Total with taxes and fees
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
Private kitchen

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
$312 nightly
The price is $354
Aug 31 - Sep 1
Total with taxes and fees
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
Outdoor spa tub

18. 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
$390 nightly
The price is $434
Aug 17 - Aug 18
Total with taxes and fees
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Smart TV, fireplace

19. 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.
$351 nightly
The price is $398
Aug 23 - Aug 24
Total with taxes and fees
Scarborough Fair walk to downtown two story apt
Coffee/tea maker, fridge, microwave, oven

20. 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.
$328 nightly
The price is $379
Aug 17 - Aug 18
Total with taxes and fees
Bend of Brothers’ | Riverfront Cottage Shenandoah
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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Clean room comfortable bed. Perfect for my short stay"
Julianne 1-night trip
Posted 3 hours ago
Comfort Inn & Suites Winchester

Find out more about Stephens City

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

Stephens City vacation 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 low season months. For more hustle and bustle, you may prefer to visit Stephens City 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 $221 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 Stephens City rentals

At Expedia, we put the best Stephens City 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 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 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 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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Stephens City?

Yes, there are vacation rentals in Stephens City near Appleland Sports Center, or you can choose a more remote option if you're looking for a relaxing stay. Our travelers 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 vacation rentals that Stephens City has to offer?

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub: Visitors like this Stephens City vacation home rental. It is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Stephens City?

With 4 Expedia vacation rentals, you're sure 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 larger area, you’ll find Valerie Hill Winery and Dinosaur Land.

What’s a vacation rental in Stephens City like?

A vacation rental is a private property where you can stay for short or long periods in Stephens City. Vacation rentals feature amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for family trips or small group gatherings.