A mountainous landscape with autumn foliage.

Stephens City Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

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, (13 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$1,137
HK$1,440 total
includes taxes & fees
13 Sept - 14 Sept
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, (38 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is HK$1,058
HK$1,728 total
includes taxes & fees
7 Sept - 8 Sept
Mountain View Bungalow in Front Royal
A kitchen with a white countertop, a sink, a coffee maker, and a window with a view of trees.

3. Pretty Little Apt by the Train II

Pretty Little Apt by the Train II
Old Town Winchester
9.6 out of 10, Exceptional, (9 reviews)
"Perfect location for walking around Old Town Winchester!"
United States
Clint B.
The price is HK$1,019
HK$1,706 total
includes taxes & fees
7 Sept - 8 Sept
Pretty Little Apt by the Train II
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

4. 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, (2 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 HK$1,160
HK$2,052 total
includes taxes & fees
17 Sept - 18 Sept
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
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 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
8.0 out of 10, Very good, (2 reviews)
"Small but appropriately priced."
United States
John M.
The price is HK$862
HK$1,519 total
includes taxes & fees
9 Sept - 10 Sept
Rosamond nice downtown studio apt
A living room with a blue sofa, a wooden coffee table, a white armchair, and a dining area with a mirror and flowers.

7. 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$1,082
HK$1,803 total
includes taxes & fees
7 Sept - 8 Sept
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

8. 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, (8 reviews)
"We had a wonderful 10-day stay with our dogs at this beautiful property. The area is great, with quick access to many things. There are many really nice, small details about the home that we enjoyed. The large table was great for our 3000-piece puzzle, and the dogs enjoyed running around the property and down by the creek. Everything was very clean, and the kitchen, although low on cooking supplies, was very nice for cooking our meals. Sadly, it rained almost every day, but we were able to enjoy...
United States
Brian F.
The price is HK$1,649
HK$3,102 total
includes taxes & fees
23 Sept - 24 Sept
Chalet w/Hot Tub, Deck, Game Room & EV Charger
A white building with a black door and a set of blue-painted stairs with black railings.

9. 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$1,510 total
includes taxes & fees
30 Sept - 1 Oct
The Blue Door steps from Handley Library
A living room with a sofa, armchair, coffee table, and a television.

10. Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.2 out of 10, Wonderful, (18 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$1,450
HK$2,594 total
includes taxes & fees
8 Sept - 9 Sept
Nostalgia Lane in the heart of the city
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.
The price is HK$1,396
HK$2,567 total
includes taxes & fees
22 Sept - 23 Sept
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
9.6 out of 10, Exceptional, (9 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$1,552
HK$2,683 total
includes taxes & fees
13 Sept - 14 Sept
Cameron Charmer pristine downtown apt with double master suites
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, (8 reviews)
"Beautiful space; helpful host."
United States
Sally C.
The price is HK$1,529
HK$1,981 total
includes taxes & fees
7 Sept - 8 Sept
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
A bedroom with a bed, a bedside table with a lamp, and a framed picture on the wall.

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

Downtown Apt 2 • 2BR • Near Park & River • Private
Front Royal
The price is HK$1,185
HK$2,014 total
includes taxes & fees
7 Sept - 8 Sept
Downtown Apt 2 • 2BR • Near Park & River • Private
A modern living room with a fireplace, a round coffee table, and a comfortable seating area.

15. Indigo Blue modern open vibe on tree lined street

Indigo Blue modern open vibe on tree lined street
Winchester Historic District
9.8 out of 10, Exceptional, (15 reviews)
"We had a great stay! The place was very clean and exactly as described. Michele communicated clearly and responded quickly, which made everything easy from check-in to check-out. The location was also perfect—very close to downtown and convenient to everything we wanted to do. We would definitely stay here again and highly recommend it to others!"
United States
Elaina R.
The price is HK$1,725
HK$3,162 total
includes taxes & fees
7 Sept - 8 Sept
Indigo Blue modern open vibe on tree lined street
A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a framed picture on the wall.

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

Downtown Apt 3 • 2BR • Near Park & River • Private
Front Royal
The price is HK$1,185
HK$2,014 total
includes taxes & fees
7 Sept - 8 Sept
Downtown Apt 3 • 2BR • Near Park & River • Private
A white door with a built-in washer and dryer unit.

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

Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
Front Royal
The price is HK$1,265
HK$2,374 total
includes taxes & fees
7 Sept - 8 Sept
Downtown Apt.1 • 2BR/2BA• Near Park/River• Private
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

18. 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
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
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, (15 reviews)
"Unique and adorable little place on the river. Perfectly clean and comfortable. We would definitely book again!"
United States
Hailey
The price is HK$2,293
HK$3,417 total
includes taxes & fees
7 Sept - 8 Sept
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A dining area with a white table and bench, a hanging light fixture, and a door leading to another room.

20. 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$1,607
HK$2,905 total
includes taxes & fees
20 Sept - 21 Sept
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Stephens City Hotel Reviews

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

10/10 Excellent
"The entire building and of course my room was very clean. Staff was very helpful at the front desk."
Ronald 1-night trip
Posted 16 hours ago
Holiday Inn Express Woodstock-Shenandoah Valley by IHG

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 Lake Frederick Boat Launch. 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.