A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Winchester Vacation 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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Winchester vacation rentals

A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

1. 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 ￥23,277
￥39,738 total
includes taxes & fees
Oct 5 - Oct 6
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A modern kitchen with white cabinetry, a central island, a dining area with a wooden table and chairs, and a built-in oven.

2. 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, (12 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
The price is ￥30,670
￥38,314 total
includes taxes & fees
Sep 29 - Sep 30
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
A two-story house with a front porch, a mailbox, and a number plate.

3. 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 ￥31,141
￥52,212 total
includes taxes & fees
Sep 29 - Sep 30
Cameron Charmer pristine downtown apt with double master suites
A living room with a sofa, armchair, coffee table, and a television.

4. 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 ￥29,097
￥49,896 total
includes taxes & fees
Sep 29 - Sep 30
Nostalgia Lane in the heart of the city
A living room with a sofa, a coffee table, a fireplace, a television, and a dining area in the background.

5. Scarborough Fair walk to downtown two story apt

Scarborough Fair walk to downtown two story apt
Old Town Winchester
9.6 out of 10, Exceptional, (8 reviews)
"amazing location, felt like home, lots of space!"
United States
Brandi M.
The price is ￥34,916
￥58,271 total
includes taxes & fees
Sep 29 - Sep 30
Scarborough Fair walk to downtown two story apt
A living room with a sofa, ottoman, lamp, and a mirror.

6. 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 ￥27,996
￥48,648 total
includes taxes & fees
Oct 1 - Oct 2
Morocco Loft 2BR overlooking city walking mall
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 ￥21,705
￥36,175 total
includes taxes & fees
Sep 29 - Sep 30
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

8. 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 ￥17,301
￥30,294 total
includes taxes & fees
Sep 29 - Sep 30
Rosamond nice downtown studio apt
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

9. 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 ￥11,796
￥37,536 total
includes taxes & fees
Sep 29 - Sep 30
The Queen of Winchester Three Bedroom with Upper Level Deck
A dining area with a white table and bench, a hanging light fixture, and a door leading to another room.

10. 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)
The price is ￥32,242
￥55,241 total
includes taxes & fees
Oct 5 - Oct 6
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

11. 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 ￥29,569
￥52,213 total
includes taxes & fees
Oct 27 - Oct 28
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
A hot tub in front of a wooden cabin with a tree in the background.

12. 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 ￥22,806
￥28,885 total
includes taxes & fees
Oct 25 - Oct 26
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.

13. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (43 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is ￥21,233
￥34,136 total
includes taxes & fees
Sep 29 - Sep 30
Mountain View Bungalow in Front Royal
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

14. 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 ￥46,004
￥64,683 total
includes taxes & fees
Sep 29 - Sep 30
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A covered outdoor area with a fire pit, seating, and a view of the landscape.

15. Mountaintop Cottage | Private Hot Tub

Mountaintop Cottage | Private Hot Tub
Front Royal
9.8 out of 10, Exceptional, (27 reviews)
"Excellent location and amazing reviews. Would definitely plan to arrive while it’s light out for the first time as the road does get a little rough at the top but we did all make it in 2WD vehicles"
United States
Sara Z.
The price is ￥58,508
￥103,048 total
includes taxes & fees
Sep 30 - Oct 1
Mountaintop Cottage | Private Hot Tub
A hot tub on an outdoor deck with a view of trees and hills.

16. Mountain View Cottage | Hot Tub & Game Room

Mountain View Cottage | Hot Tub & Game Room
Front Royal
9.8 out of 10, Exceptional, (17 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is ￥52,374
￥105,997 total
includes taxes & fees
Sep 29 - Sep 30
Mountain View Cottage | Hot Tub & Game Room
A hot tub area with a wooden structure overhead, a bottle, and glasses.

17. Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
9.6 out of 10, Exceptional, (39 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
United States
Felice N.
The price is ￥61,559
￥113,872 total
includes taxes & fees
Oct 22 - Oct 23
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
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
The price is ￥18,087
￥30,294 total
includes taxes & fees
Sep 30 - Oct 1
The Blue Door steps from Handley Library
A modern kitchen with a black countertop, wooden dining table, and a view of the outdoors through large sliding glass doors.

19. Mountain cabin near national park & wineries

Mountain cabin near national park & wineries
Linden
9.8 out of 10, Exceptional, (36 reviews)
"It was a great place to stay and very clean."
United States
Chynna V.
The price is ￥29,726
￥63,148 total
includes taxes & fees
Sep 29 - Sep 30
Mountain cabin near national park & wineries
A wooden cabin with a garage, surrounded by trees and a gravel driveway.

20. The Pond Cabin

The Pond Cabin
2.0 star property
Linden
The price is ￥37,590
￥71,822 total
includes taxes & fees
Oct 20 - Oct 21
The Pond Cabin
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 Winchester Hotel Reviews

Skyland

Skyland

10/10 Excellent
"Loved staying here. The rooms are nice for being around 30+ years old and while the walls are thin (and you can definitely hear EVERYTHING your neighbors are doing) it was still a great time and the views were fantastic. Dinner and lunch (while super expensive) were delicious and worth the money."
Andrew 2-night trip
Posted 1 hour ago
Skyland

Find out more about Winchester

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

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

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

Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we offer vacation rentals in Winchester near Shenandoah Valley Discovery Museum, or you can go with a secluded option if you want a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theater scene while you're visiting.

What are some of the best vacation home rentals in Winchester?

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails: This vacation home near Winchester 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 will I find in Winchester?

Choose from 15 Expedia vacation rentals in Winchester for a memorable vacation.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Rocking S Ranch are a couple of family-friendly sights, whereas cultural attractions include Bright Box Theater and Museum of the Shenandoah Valley. Other places in town to visit include Patsy Cline Historic House and Apple Blossom Mall.

What’s a vacation rental in Winchester like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Winchester. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for family trips.