A mountainous landscape with autumn foliage.

Stephens City Vacation Rentals

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Our top choices for Stephens City vacation rentals

1. 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, (11 reviews)
"Loved the house and privacy it provided. Relaxing getaway and it was furnished nicely. Slippers and robes added an extra touch. Communication was stellar."
United States
Rebekah G.
The price is CA $261
CA $556 total
includes taxes & fees
Nov 3 - Nov 4
Chalet w/Hot Tub, Deck, Game Room & EV Charger

2. 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.
The price is CA $211
CA $373 total
includes taxes & fees
Oct 19 - Oct 20
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!

3. 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 CA $191
CA $316 total
includes taxes & fees
Oct 21 - Oct 22
Mountain View Bungalow in Front Royal

4. 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, (14 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
The price is CA $276
CA $356 total
includes taxes & fees
Oct 19 - Oct 20
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC

5. Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (3 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is CA $227
CA $431 total
includes taxes & fees
Oct 19 - Oct 20
Morocco Loft 2BR overlooking city walking mall

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

Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
Front Royal
9.8 out of 10, Exceptional, (16 reviews)
"Unique and adorable little place on the river. Perfectly clean and comfortable. We would definitely book again!"
United States
Hailey
The price is CA $414
CA $616 total
includes taxes & fees
Oct 26 - Oct 27
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub

7. 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, (10 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 CA $280
CA $500 total
includes taxes & fees
Oct 19 - Oct 20
Cameron Charmer pristine downtown apt with double master suites

8. 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 CA $239
CA $467 total
includes taxes & fees
Oct 19 - Oct 20
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything

9. 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
The price is CA $141
CA $248 total
includes taxes & fees
Nov 11 - Nov 12
Cozy English Basement Apt quiet but close to downtown

10. 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 CA $113
CA $363 total
includes taxes & fees
Nov 2 - Nov 3
The Queen of Winchester Three Bedroom with Upper Level Deck

11. Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.8 out of 10, Excellent, (3 reviews)
"Easy space for a 2 person weekend getaway, very close within walking distance to food, shops, breweries, etc"
United States
Jameson D.
The price is CA $156
CA $276 total
includes taxes & fees
Nov 2 - Nov 3
Rosamond nice downtown studio apt

12. 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 CA $290
CA $532 total
includes taxes & fees
Oct 19 - Oct 20
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library

13. Shenandoah River House | 3BR - Private Dock - Pets

Shenandoah River House | 3BR - Private Dock - Pets
Front Royal
The price is CA $226
CA $596 total
includes taxes & fees
Oct 19 - Oct 20
Shenandoah River House | 3BR - Private Dock - Pets

14. 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 CA $262
CA $476 total
includes taxes & fees
Oct 19 - Oct 20
Nostalgia Lane in the heart of the city

15. Downtown Apt 3 • 2BR • Near Park & River • Private

Downtown Apt 3 • 2BR • Near Park & River • Private
Front Royal
The price is CA $206
CA $382 total
includes taxes & fees
Oct 19 - Oct 20
Downtown Apt 3 • 2BR • Near Park & River • Private

16. 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 CA $156
CA $284 total
includes taxes & fees
Nov 2 - Nov 3
The Stock Exchange downtown 3rd floor studio apt

17. Downtown Apt.1 • 2BR/2BA• Near Park/River• Private

Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
Front Royal
The price is CA $214
CA $409 total
includes taxes & fees
Oct 20 - Oct 21
Downtown Apt.1 • 2BR/2BA• Near Park/River• Private

18. The Blue Door steps from Handley Library

The Blue Door steps from Handley Library
Old Town Winchester
5.4 out of 10, (3 reviews)
"Perfect. Met all expectations. Small but Great."
United States
derric3k
The price is CA $163
CA $276 total
includes taxes & fees
Oct 26 - Oct 27
The Blue Door steps from Handley Library

19. Downtown Apt 2 • 2BR • Near Park & River • Private

Downtown Apt 2 • 2BR • Near Park & River • Private
Front Royal
The price is CA $206
CA $382 total
includes taxes & fees
Oct 19 - Oct 20
Downtown Apt 2 • 2BR • Near Park & River • Private

20. Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
Front Royal
9.6 out of 10, Exceptional, (9 reviews)
"Unique accommodation overlooking a beautiful valley with many convenient modern features such as a EV charger provider"
United States
Paul S.
The price is CA $722
CA $899 total
includes taxes & fees
Oct 22 - Oct 23
Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Stephens City. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails: Visitors like this Stephens City vacation home rental. It is located in a rural location and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Stephens City?

With 5 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 Shenandoah River. 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.