Stephens City Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Stephens City vacation rentals

A hot tub in front of a wooden cabin with a tree in the background.

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, (15 reviews)
"This tiny house was an absolute dream to stay at! Jen is very attentive to detail- everything from the decor to the thoughtful welcome basket and supplying a feed bucket for the farm animals was perfection. My kids requested our next vacation just be there instead! "
United States
Laura H.
$157 nightly
The price is $175
Nov 16 - Nov 17
Total with taxes and fees
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

2. 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.
$227 nightly
The price is $244
Nov 30 - Dec 1
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.

3. 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.
$162 nightly
The price is $184
Nov 12 - Nov 13
Total with taxes and fees
Rosamond nice downtown studio apt
A modern living room with a sofa, a coffee table, and a lamp. There is a kitchen area in the background with cabinets and a painting on the wall.

4. Executive Suites

Executive Suites
3.0 star property
Winchester
$212 nightly
The price is $240
Dec 12 - Dec 13
Total with taxes and fees
Executive Suites
A wooden deck with white railings and a covered porch area.

5. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (51 reviews)
"It was great and beautiful place to staying. Thanks for hospitality"
United States
Onon
$184 nightly
The price is $205
Nov 22 - Nov 23
Total with taxes and fees
Mountain View Bungalow in Front Royal
A lakeside property with a dock, a wooden deck, and a house surrounded by dense greenery.

6. Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6

Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
Front Royal
9.4 out of 10, Exceptional, (3 reviews)
"The gravel road to get to the properly is an adventure. The owner described it perfectly."
United States
Denise A.
$349 nightly
The price is $385
Nov 12 - Nov 13
Total with taxes and fees
Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
A modern, dark-colored triangular building with a balcony and outdoor seating area.

7. 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)
"A wonderful place to relax and enjoy being with family or friends, with lots of room for the dogs to run and play!"
United States
Laura V.
$351 nightly
The price is $385
Nov 30 - Dec 1
Total with taxes and fees
Chalet w/Hot Tub, Deck, Game Room & EV Charger
A living room with a blue sofa, a wooden coffee table, a white armchair, and a dining area with a mirror and flowers.

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
8.4 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.
$190 nightly
The price is $215
Nov 15 - Nov 16
Total with taxes and fees
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

9. 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.
$219 nightly
The price is $248
Nov 19 - Nov 20
Total with taxes and fees
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A building with a red door, white trim, and a small balcony with a metal railing.

10. 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.
$167 nightly
The price is $189
Nov 12 - Nov 13
Total with taxes and fees
The Stock Exchange downtown 3rd floor studio apt
A living room with a sofa, ottoman, lamp, and a mirror.

11. 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.
$253 nightly
The price is $287
Nov 12 - Nov 13
Total with taxes and fees
Morocco Loft 2BR overlooking city walking mall
A two-story house with a front porch, a mailbox, and a number plate.

12. Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.8 out of 10, Exceptional, (11 reviews)
"The property was exceptional and very comfortable. We enjoyed the amenities. We would book it for future trips again."
United States
Carolyn F.
$294 nightly
The price is $333
Nov 12 - Nov 13
Total with taxes and fees
Cameron Charmer pristine downtown apt with double master suites
A sign for Shenandoah National Park's North Entrance.

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

Downtown Apt 2 • 2BR • Near Park & River • Private
Front Royal
$256 nightly
The price is $280
Nov 16 - Nov 17
Total with taxes and fees
Downtown Apt 2 • 2BR • Near Park & River • Private
A black door with the number 415, a window, and a hanging flower basket.

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

Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
Front Royal
10.0 out of 10, Exceptional, (1 review)
"Perfect for a quick stay over when going to shenedoah natl park. Location is awesome. Very clean and spacious! Highly recommend!"
United States
Maureen N.
$265 nightly
The price is $291
Nov 12 - Nov 13
Total with taxes and fees
Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
A living room with a sofa, armchair, coffee table, and a television.

15. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.0 out of 10, Wonderful, (22 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
$270 nightly
The price is $306
Nov 15 - Nov 16
Total with taxes and fees
Nostalgia Lane in the heart of the city
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

16. 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
$373 nightly
The price is $415
Nov 12 - Nov 13
Total with taxes and fees
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A sign for Shenandoah National Park's North Entrance.

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

Downtown Apt 3 • 2BR • Near Park & River • Private
Front Royal
10.0 out of 10, Exceptional, (1 review)
"This property is absolutely perfect: great location for walking through the historic part of town, close to food & fun, very well appointed (right down to quality toilet paper!) & perfectly clean. Yuliya responded very quickly from the moment I made the reservation to checkout. We would stay again for sure! Thank you, Yuliya & Mark!"
United States
kim B.
$248 nightly
The price is $273
Nov 12 - Nov 13
Total with taxes and fees
Downtown Apt 3 • 2BR • Near Park & River • Private
A wooden cabin with a metal roof, surrounded by trees, and featuring outdoor seating and a fire pit.

18. 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.
$490 nightly
The price is $540
Nov 15 - Nov 16
Total with taxes and fees
Skyline Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
A garden with a wooden swing set and a circular seating area.

19. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (57 reviews)
"We enjoyed our stay here. The property was lovely and the house was nicely stocked and decorated. We will definitely stay again when in the area!"
United States
Marsha N.
Newly renovated Farm cottage with Mountain views
A two-story house with a balcony, surrounded by trees and snow.

20. Cozy A frame cabin in quaint Front Royal. Dog friendly

Cozy A frame cabin in quaint Front Royal. Dog friendly
Front Royal
9.4 out of 10, Exceptional, (11 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
$243 nightly
The price is $268
Nov 12 - Nov 13
Total with taxes and fees
Cozy A frame cabin in quaint Front Royal. Dog friendly
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

A stately house with a well-manicured lawn, a patio with outdoor furniture, and a view of the surrounding greenery.
Glen Gordon Manor

Glen Gordon Manor

Glen Gordon Manor
Huntly

10/10 Excellent

Perfect
United States
Omar
Reviewed June 16, 2026
Glen Gordon Manor

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 $174 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.

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.

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