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

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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 ￥23,411
￥41,399 total
includes taxes & fees
Oct 12 - Oct 13
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

2. 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 ￥17,380
￥30,432 total
includes taxes & fees
Oct 11 - Oct 12
Rosamond nice downtown studio apt
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

3. 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 ￥13,287
￥40,722 total
includes taxes & fees
Nov 2 - Nov 3
The Queen of Winchester Three Bedroom with Upper Level Deck
A living room with a blue sofa, a wooden coffee table, a white armchair, and a dining area with a mirror and flowers.

4. 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 ￥21,804
￥37,056 total
includes taxes & fees
Oct 11 - Oct 12
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A narrow bathroom with a toilet, sink, and mirror. There is a towel ring and a flower-patterned floor.

5. 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 ￥28,124
￥51,557 total
includes taxes & fees
Oct 18 - Oct 19
Morocco Loft 2BR overlooking city walking mall
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

6. 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 ￥26,734
￥51,772 total
includes taxes & fees
Oct 18 - Oct 19
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.

7. 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 ￥22,936
￥29,050 total
includes taxes & fees
Oct 20 - Oct 21
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A white building with a black door and a set of blue-painted stairs with black railings.

8. 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 ￥18,170
￥30,432 total
includes taxes & fees
Oct 11 - Oct 12
The Blue Door steps from Handley Library
A building with a red door, white trim, and a small balcony with a metal railing.

9. 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 ￥17,380
￥31,328 total
includes taxes & fees
Nov 8 - Nov 9
The Stock Exchange downtown 3rd floor studio apt
A modern kitchen with white cabinetry, a central island, a dining area with a wooden table and chairs, and a built-in oven.

10. 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, (14 reviews)
"Perfect location and unique and charming house."
United States
Heather O.
The price is ￥30,810
￥39,920 total
includes taxes & fees
Oct 11 - Oct 12
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.

11. 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 ￥31,284
￥55,673 total
includes taxes & fees
Oct 18 - Oct 19
Cameron Charmer pristine downtown apt with double master suites
A living room with a sofa, armchair, coffee table, and a television.

12. 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, (20 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 ￥29,230
￥52,630 total
includes taxes & fees
Oct 11 - Oct 12
Nostalgia Lane in the heart of the city
A wooden cabin with a porch, a bench, and a table.

13. Peaceful mountain cabin in charming Berryville VA - next to river and brewery

Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Berryville
10.0 out of 10, Exceptional, (3 reviews)
"Loved the place, the log cabin has the old world charm and beautiful settings. "
United States
Anonymous traveler
The price is ￥11,864
￥38,908 total
includes taxes & fees
Oct 12 - Oct 13
Peaceful mountain cabin in charming Berryville VA - next to river and brewery
A dining area with a white table and bench, a hanging light fixture, and a door leading to another room.

14. 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 ￥32,390
￥58,537 total
includes taxes & fees
Oct 11 - Oct 12
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
A living room with a sofa, a coffee table, a fireplace, a television, and a dining area in the background.

15. 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 ￥35,076
￥62,476 total
includes taxes & fees
Oct 13 - Oct 14
Scarborough Fair walk to downtown two story apt
A wooden deck with white railings and a covered porch area.

16. 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 ￥21,354
￥35,035 total
includes taxes & fees
Oct 18 - Oct 19
Mountain View Bungalow in Front Royal
A garden with a wooden swing set and a circular seating area.

17. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (54 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.
The price is ￥22,752
￥48,448 total
includes taxes & fees
Oct 22 - Oct 23
Newly renovated Farm cottage with Mountain views
A single-story brick building with a front porch, a picnic table, and a barbecue grill.

18. Shenandoah River House | 3BR - Private Dock - Pets

Shenandoah River House | 3BR - Private Dock - Pets
Front Royal
The price is ￥23,917
￥67,206 total
includes taxes & fees
Oct 13 - Oct 14
Shenandoah River House | 3BR - Private Dock - Pets
A bedroom with a bed, bedside table, lamp, and a window with curtains.

19. 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)
"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 ￥40,712
￥75,592 total
includes taxes & fees
Nov 3 - Nov 4
Chalet w/Hot Tub, Deck, Game Room & EV Charger
A hot tub area with a wooden structure overhead, a bottle, and glasses.

20. 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 ￥55,332
￥110,526 total
includes taxes & fees
Oct 22 - Oct 23
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
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 Winchester Hotel Reviews

Mimslyn Inn Historic Hotels Of America

Mimslyn Inn Historic Hotels Of America

8/10 Good
"The room was very clean and larger than expected. It would have been nice to have more than 2 hangers in the closet. Our room was on the first floor, closest to the front desk and to the door to the stairwell, so there was quite alot of noise after "quiet" hours and before 7 a.m. Just wish it had been quieter in order to get a good (two) night's sleep. I might stay again, but would request a room on the upper floor."
Tina 2-night trip
Posted 10 hours ago
Mimslyn Inn Historic Hotels Of America

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
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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.