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Stephens City Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Stephens City vacation rentals

A bedroom with a bed, bedside table, lamp, and a window with curtains.

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.
$326 nightly
The price is $358
Oct 28 - Oct 29
Total with taxes and fees
Chalet w/Hot Tub, Deck, Game Room & EV Charger
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

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
10.0 out of 10, Exceptional, (4 reviews)
$232 nightly
The price is $263
Oct 19 - Oct 20
Total with taxes and fees
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A wooden deck with white railings and a covered porch area.

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.
$200 nightly
The price is $223
Oct 18 - Oct 19
Total with taxes and fees
Mountain View Bungalow in Front Royal
A modern kitchen with white cabinetry, a central island, a dining area with a wooden table and chairs, and a built-in oven.

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.
$222 nightly
The price is $252
Oct 18 - Oct 19
Total with taxes and fees
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
A living room with a sofa, ottoman, lamp, and a mirror.

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.
$268 nightly
The price is $304
Oct 18 - Oct 19
Total with taxes and fees
Morocco Loft 2BR overlooking city walking mall
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

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
$392 nightly
The price is $436
Oct 26 - Oct 27
Total with taxes and fees
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A two-story house with a front porch, a mailbox, and a number plate.

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.
$311 nightly
The price is $352
Oct 18 - Oct 19
Total with taxes and fees
Cameron Charmer pristine downtown apt with double master suites
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

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
$289 nightly
The price is $328
Oct 18 - Oct 19
Total with taxes and fees
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
A wooden deck with wicker furniture, including two chairs and a small table with a candle.

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 traveler
$155 nightly
The price is $176
Nov 11 - Nov 12
Total with taxes and fees
Cozy English Basement Apt quiet but close to downtown
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

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.
$243 nightly
The price is $253
Nov 2 - Nov 3
Total with taxes and fees
The Queen of Winchester Three Bedroom with Upper Level Deck
A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

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.
$170 nightly
The price is $193
Nov 2 - Nov 3
Total with taxes and fees
Rosamond nice downtown studio apt
A dining area with a white table and bench, a hanging light fixture, and a door leading to another room.

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.
$330 nightly
The price is $374
Oct 18 - Oct 19
Total with taxes and fees
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
A single-story brick building with a front porch, a picnic table, and a barbecue grill.

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

Shenandoah River House | 3BR - Private Dock - Pets
Front Royal
$379 nightly
The price is $418
Oct 28 - Oct 29
Total with taxes and fees
Shenandoah River House | 3BR - Private Dock - Pets
A living room with a sofa, armchair, coffee table, and a television.

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.
$295 nightly
The price is $334
Oct 19 - Oct 20
Total with taxes and fees
Nostalgia Lane in the heart of the city
A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a framed picture on the wall.

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

Downtown Apt 3 • 2BR • Near Park & River • Private
Front Royal
$244 nightly
The price is $267
Oct 18 - Oct 19
Total with taxes and fees
Downtown Apt 3 • 2BR • Near Park & River • Private
A building with a red door, white trim, and a small balcony with a metal railing.

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.
$175 nightly
The price is $198
Nov 2 - Nov 3
Total with taxes and fees
The Stock Exchange downtown 3rd floor studio apt
A bedroom with a bed, two windows with curtains, a bedside table, a chair, and a door.

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

Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
Front Royal
$263 nightly
The price is $288
Oct 20 - Oct 21
Total with taxes and fees
Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
A white building with a black door and a set of blue-painted stairs with black railings.

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
$171 nightly
The price is $194
Oct 26 - Oct 27
Total with taxes and fees
The Blue Door steps from Handley Library
A bedroom with a bed, bedside tables, a ceiling fan, and a window.

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

Downtown Apt 2 • 2BR • Near Park & River • Private
Front Royal
$244 nightly
The price is $267
Oct 18 - Oct 19
Total with taxes and fees
Downtown Apt 2 • 2BR • Near Park & River • Private
A wooden cabin with a metal roof, surrounded by trees, and featuring outdoor seating and a fire pit.

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.
$671 nightly
The price is $740
Nov 16 - Nov 17
Total with taxes and fees
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

Spark by Hilton Winchester

Spark by Hilton Winchester

10/10 Excellent
"I loved how the lobby was decorated for the Halloween season. It was done very well. Made it quite memorable!"
Marlene 1-night trip
Posted 5 hours ago
Spark by Hilton 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?

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.