A mountainous landscape with autumn foliage.

Stephens City Holiday Rentals

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Check prices for these dates

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

Our top choices for Stephens City holiday 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 HK$1,138
HK$1,441 total
includes taxes & fees
22 Nov - 23 Nov
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 HK$1,059
HK$1,755 total
includes taxes & fees
29 Oct - 30 Oct
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 HK$1,502
HK$3,135 total
includes taxes & fees
27 Oct - 28 Oct
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.
The price is HK$785
HK$1,378 total
includes taxes & fees
11 Nov - 12 Nov
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 HK$612
HK$1,979 total
includes taxes & fees
28 Oct - 29 Oct
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 HK$863
HK$1,512 total
includes taxes & fees
2 Nov - 3 Nov
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 HK$1,397
HK$2,561 total
includes taxes & fees
26 Oct - 27 Oct
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 HK$1,086
HK$3,076 total
includes taxes & fees
28 Oct - 29 Oct
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 HK$1,083
HK$1,840 total
includes taxes & fees
22 Nov - 23 Nov
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 HK$1,328
HK$2,553 total
includes taxes & fees
3 Nov - 4 Nov
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 HK$1,554
HK$2,757 total
includes taxes & fees
25 Oct - 26 Oct
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 HK$902
HK$1,511 total
includes taxes & fees
25 Oct - 26 Oct
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 HK$1,530
HK$2,748 total
includes taxes & fees
25 Oct - 26 Oct
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 HK$1,143
HK$2,114 total
includes taxes & fees
26 Oct - 27 Oct
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 HK$1,187
HK$2,243 total
includes taxes & fees
25 Oct - 26 Oct
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 HK$1,020
HK$1,761 total
includes taxes & fees
21 Nov - 22 Nov
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 HK$1,452
HK$2,560 total
includes taxes & fees
22 Nov - 23 Nov
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 HK$1,609
HK$2,934 total
includes taxes & fees
27 Oct - 28 Oct
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

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
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 HK$1,143
HK$2,114 total
includes taxes & fees
26 Oct - 27 Oct
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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

8/10 Good
"It was a nice hotel."
Eric 1-night trip
Posted 7 hours ago
Comfort Inn & Suites Winchester

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
  • Use the map to find apartments and other holiday homes in the Stephens City neighbourhood you prefer
  • 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 holiday rentals in Stephens City?

Yes, there are holiday rentals in Stephens City close to Appleland Sports Center, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Stephens City has to offer?

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails: This holiday home rental outside of Stephens City is located in a rural location, and has a fireplace, a balcony and a BBQ 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 holiday with amenities such as a selection of games.

How many holiday rentals are there in Stephens City?

With 5 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Valerie Hill Winery and Dinosaur Land.

What’s a holiday rental in Stephens City like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Stephens City. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for small groups.