A mountainous landscape with autumn foliage.

Stephens City Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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, (14 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 ￥22,726
￥28,784 total
includes taxes & fees
Nov 19 - Nov 20
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A wooden deck with white railings and a covered porch area.

2. 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 ￥21,159
￥35,063 total
includes taxes & fees
Nov 2 - Nov 3
Mountain View Bungalow in Front Royal
A modern bathroom with a double sink vanity, two wall-mounted mirrors, and a towel rack.

3. 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 ￥33,829
￥67,288 total
includes taxes & fees
Nov 4 - Nov 5
Chalet w/Hot Tub, Deck, Game Room & EV Charger
A wooden deck with wicker furniture, including two chairs and a small table with a candle.

4. 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)
"Great location and extremely easy in and out. Cute and clever little apartment. Quirky kitchen set up, but absolutely everything was provided, and I cooked 9 out of 10 nights."
United States
Wayne C.
Cozy English Basement Apt quiet but close to downtown
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

5. 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 ￥11,863
￥39,362 total
includes taxes & fees
Oct 26 - Oct 27
The Queen of Winchester Three Bedroom with Upper Level Deck
A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

6. 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 ￥17,399
￥30,644 total
includes taxes & fees
Nov 12 - Nov 13
Rosamond nice downtown studio apt
A living room with a sofa, ottoman, lamp, and a mirror.

7. 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 ￥27,898
￥51,143 total
includes taxes & fees
Oct 29 - Oct 30
Morocco Loft 2BR overlooking city walking mall
A modern kitchen with white cabinetry, a central island with stools, a ceiling fan, and a view to the outdoors.

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

Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
Front Royal
The price is ￥21,691
￥61,439 total
includes taxes & fees
Oct 28 - Oct 29
Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
A living room with a blue sofa, a wooden coffee table, a white armchair, and a dining area with a mirror and flowers.

9. 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.
The price is ￥21,629
￥36,758 total
includes taxes & fees
Nov 22 - Nov 23
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

10. 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 ￥26,519
￥51,356 total
includes taxes & fees
Nov 1 - Nov 2
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
A two-story house with a front porch, a mailbox, and a number plate.

11. 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.
The price is ￥31,033
￥54,695 total
includes taxes & fees
Nov 8 - Nov 9
Cameron Charmer pristine downtown apt with double master suites
A room with a radiator, a wooden rocking chair, a door, and a window with a lace curtain.

12. 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 ￥18,024
￥30,188 total
includes taxes & fees
Nov 8 - Nov 9
The Blue Door steps from Handley Library
A modern kitchen with white cabinetry, a central island, a dining area with a wooden table and chairs, and a built-in oven.

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, (15 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
The price is ￥30,562
￥54,871 total
includes taxes & fees
Oct 26 - Oct 27
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
A bedroom with a bed, a nightstand, a ceiling fan, and a bathroom visible through an open door.

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

Downtown Apt 2 • 2BR • Near Park & River • Private
Front Royal
The price is ￥22,820
￥42,218 total
includes taxes & fees
Oct 26 - Oct 27
Downtown Apt 2 • 2BR • Near Park & River • Private
A mountainous landscape with rolling hills and dense forest.

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

Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
Front Royal
The price is ￥23,698
￥44,786 total
includes taxes & fees
Oct 25 - Oct 26
Downtown Apt.1 • 2BR/2BA• 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.
The price is ￥17,240
￥31,076 total
includes taxes & fees
Nov 15 - Nov 16
The Stock Exchange downtown 3rd floor studio apt
A living room with a sofa, armchair, coffee table, and a television.

17. 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 ￥28,995
￥51,320 total
includes taxes & fees
Nov 1 - Nov 2
Nostalgia Lane in the heart of the city
A dining area with a white table and bench, a hanging light fixture, and a door leading to another room.

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 ￥32,130
￥58,600 total
includes taxes & fees
Oct 26 - Oct 27
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
A bedroom with a large bed, a bedside table with a lamp, a ceiling fan, and a dresser with a mirror.

19. 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 ￥45,844
￥68,296 total
includes taxes & fees
Oct 26 - Oct 27
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a framed picture on the wall.

20. 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.
The price is ￥22,820
￥42,218 total
includes taxes & fees
Oct 26 - Oct 27
Downtown Apt 3 • 2BR • Near Park & River • Private
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

Ramada by Wyndham Strasburg/Shenandoah Valley

Ramada by Wyndham Strasburg/Shenandoah Valley

10/10 Excellent
"A really great hotel for the price"
Glenn 1-night trip
Posted 8 hours ago
Ramada by Wyndham Strasburg/Shenandoah Valley

Find out more about Stephens City

Search for holiday rentals in Stephens City on Expedia! You can easily find your home rentals, villas, holiday apartments in Stephens City using one of the methods below:

  • View our selection of featured holiday rentals in Stephens City
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  • Enter your travel dates to view the best deals on holiday rentals in Stephens City while they last

Look no further and take a look at our great range of rental properties in Stephens City!

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.