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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Winchester vacation rentals

A modern apartment with a spiral staircase, a living area with a dark-colored sofa, a coffee table, and a kitchen in the background.

1. Executive Suites

Executive Suites
3.0 star property
Winchester
The price is ￥40,331
￥45,696 total
includes taxes & fees
Nov 14 - Nov 15
Executive Suites
A living room with a glass-top coffee table, wicker chairs, a sofa, and a painting on the wall.

2. 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
8.8 out of 10, Excellent, (5 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 ￥23,664
￥39,674 total
includes taxes & fees
Nov 19 - Nov 20
Cleveland Park awesome Winchester 2 BR 1st fl apt. walk to everything!
A living room with a sofa, ottoman, lamp, and a mirror.

3. 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 ￥28,439
￥49,418 total
includes taxes & fees
Nov 22 - Nov 23
Morocco Loft 2BR overlooking city walking mall
A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

4. 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.
Rosamond nice downtown studio apt
A covered deck with outdoor furniture and a grill.

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 ￥13,271
￥40,630 total
includes taxes & fees
Nov 19 - Nov 20
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.

6. 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 ￥22,048
￥35,660 total
includes taxes & fees
Nov 22 - Nov 23
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A backyard patio with a stone-tiled floor, a wooden table with chairs, a barbecue grill, and a wooden fence.

7. 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 ￥31,634
￥51,228 total
includes taxes & fees
Nov 15 - Nov 16
Cameron Charmer pristine downtown apt with double master suites
A hot tub in front of a wooden cabin with a tree in the background.

8. 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, (15 reviews)
"This tiny house was an absolute dream to stay at! Jen is very attentive to detail- everything from the decor to the thoughtful welcome basket and supplying a feed bucket for the farm animals was perfection. My kids requested our next vacation just be there instead! "
United States
Laura H.
The price is ￥23,167
￥26,853 total
includes taxes & fees
Nov 17 - Nov 18
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A living room with a sofa, coffee table, and lamps. There is a bookshelf and a framed picture on the wall.

9. 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, (22 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 ￥29,557
￥50,685 total
includes taxes & fees
Nov 22 - Nov 23
Nostalgia Lane in the heart of the city
A modern house with a large window, a covered porch, and outdoor seating.

10. 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)
"A wonderful place to relax and enjoy being with family or friends, with lots of room for the dogs to run and play!"
United States
Laura V.
The price is ￥31,053
￥61,504 total
includes taxes & fees
Nov 30 - Dec 1
Chalet w/Hot Tub, Deck, Game Room & EV Charger
A building with a red door, white trim, and a small balcony with a metal railing.

11. 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 ￥17,575
￥29,146 total
includes taxes & fees
Nov 15 - Nov 16
The Stock Exchange downtown 3rd floor studio apt
A wooden deck with a ceiling fan, white door, and windows.

12. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (51 reviews)
"It was great and beautiful place to staying. Thanks for hospitality"
United States
Onon
The price is ￥21,569
￥32,719 total
includes taxes & fees
Nov 22 - Nov 23
Mountain View Bungalow in Front Royal
A house with a fire pit in the foreground and a deck with string lights in the background.

13. The Haven at Turkey Run | Hot Tub, Creek + Disc Golf on 13 Acres | 3BR, Sleeps 6

The Haven at Turkey Run | Hot Tub, Creek + Disc Golf on 13 Acres | 3BR, Sleeps 6
Strasburg
10.0 out of 10, Exceptional, (20 reviews)
"This was the ideal isolated cabin for our trip to Northern Virginia. It was clean, well laid out, and very well stocked with everything you need. I highly recommend staying here if you are in the area!"
United States
Paul S.
The price is ￥34,376
￥77,599 total
includes taxes & fees
Nov 16 - Nov 17
The Haven at Turkey Run | Hot Tub, Creek + Disc Golf on 13 Acres | 3BR, Sleeps 6
A hot tub area with a wooden structure overhead, a bottle, and glasses.

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

Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
Boyce
9.4 out of 10, Exceptional, (40 reviews)
"Well equipped kitchen in a lovely 1950s house. This was perfect for our Team retreat."
United States
Felice N.
The price is ￥52,700
￥105,923 total
includes taxes & fees
Nov 23 - Nov 24
Pets? YES! 🐕 Hot Tub ✮ Fire Pit ✮ Fast Wi-Fi
A hot tub area with a view of a lake and trees, surrounded by ornate black metal railings and decorative lanterns.

15. 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 ￥46,733
￥66,064 total
includes taxes & fees
Nov 15 - Nov 16
Riverfront! Shenandoah River! Sleeps 4! New Hot Tub
A cozy outdoor seating area with a sofa and a fire pit, wooden deck, and a glass door leading to an interior space.

16. A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.6 out of 10, Exceptional, (14 reviews)
"Great place to stay to catch the northern entrance to Shenandoah. Comfortable beds, great furniture, and easy drive to Front Royal for dining. "
United States
Scott M.
The price is ￥21,138
￥53,803 total
includes taxes & fees
Nov 19 - Nov 20
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
A hot tub on a deck with a white railing and greenery in the background.

17. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Front Royal
9.6 out of 10, Exceptional, (9 reviews)
"Great little hideout! We loved this little place, accurately described and the communication was superb!"
United States
P H.
The price is ￥33,232
￥72,075 total
includes taxes & fees
Nov 24 - Nov 25
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
A covered outdoor area with a fire pit, seating, and a view of the landscape.

18. Mountaintop Cottage | Private Hot Tub

Mountaintop Cottage | Private Hot Tub
Front Royal
9.8 out of 10, Exceptional, (28 reviews)
"Enjoyed our stay, house was beautiful and clean. Coffee in the morning with the deer was awesome. Love the neighborhood cat Luna."
United States
Kevin D.
The price is ￥49,704
￥97,218 total
includes taxes & fees
Nov 18 - Nov 19
Mountaintop Cottage | Private Hot Tub
A lakeside property with a dock, a wooden deck, and a house surrounded by dense greenery.

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

Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
Front Royal
9.4 out of 10, Exceptional, (3 reviews)
"The gravel road to get to the properly is an adventure. The owner described it perfectly."
United States
Denise A.
The price is ￥21,473
￥61,574 total
includes taxes & fees
Nov 15 - Nov 16
Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
A two-story house with a balcony, a deck, and a stone retaining wall.

20. 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 ￥58,668
￥106,928 total
includes taxes & fees
Nov 15 - Nov 16
Mountain View Cottage | Hot Tub & Game Room
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

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"Parfait"
pascal 1-night trip
Posted 3 hours ago
Quality Inn Winchester
Days Inn by Wyndham Winchester

Days Inn by Wyndham Winchester

8/10 Good
"Convenient location right off the highway and plenty of food options such as Wawa, Sheetz etc."
Matthew 1-night trip
Posted 3 days ago
Days Inn by Wyndham Winchester

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.