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 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.
$229 nightly
The price is $259
Oct 4 - Oct 5
Total with taxes and fees
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.

2. 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.
$238 nightly
The price is $248
Oct 5 - Oct 6
Total with taxes and fees
The Queen of Winchester Three Bedroom with Upper Level Deck
A hallway with a wooden staircase, a hanging light fixture, and a welcome mat.

3. 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.
$170 nightly
The price is $193
Oct 6 - Oct 7
Total with taxes and fees
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.

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.
$207 nightly
The price is $235
Oct 4 - Oct 5
Total with taxes and fees
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
A living room with a sofa, ottoman, lamp, and a mirror.

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.
$265 nightly
The price is $300
Oct 4 - Oct 5
Total with taxes and fees
Morocco Loft 2BR overlooking city walking mall
A white building with a black door and a set of blue-painted stairs with black railings.

6. 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
$170 nightly
The price is $193
Oct 4 - Oct 5
Total with taxes and fees
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.

7. 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.
$223 nightly
The price is $253
Oct 4 - Oct 5
Total with taxes and fees
Magnolia Winds 3-bedroom apartment in charming Winchester with cool AC
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, (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.
$165 nightly
The price is $184
Oct 6 - Oct 7
Total with taxes and fees
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

9. 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
$308 nightly
The price is $349
Oct 18 - Oct 19
Total with taxes and fees
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.

10. 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.
$308 nightly
The price is $349
Oct 4 - Oct 5
Total with taxes and fees
Cameron Charmer pristine downtown apt with double master suites
A living room with a sofa, armchair, coffee table, and a television.

11. 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, (19 reviews)
"Easy access to nearby attractions. Convenient to all we hoped to see and do while we were here."
United States
Melissa J.
$294 nightly
The price is $333
Oct 4 - Oct 5
Total with taxes and fees
Nostalgia Lane in the heart of the city
A wooden deck with white railings and a covered porch area.

12. 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.
$200 nightly
The price is $223
Oct 4 - Oct 5
Total with taxes and fees
Mountain View Bungalow in Front Royal
A dining area with a white table and bench, a hanging light fixture, and a door leading to another room.

13. 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.
$327 nightly
The price is $370
Oct 4 - Oct 5
Total with taxes and fees
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.

14. 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.
$346 nightly
The price is $392
Oct 4 - Oct 5
Total with taxes and fees
Scarborough Fair walk to downtown two story apt
A garden with a wooden swing set and a circular seating area.

15. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (52 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.
$277 nightly
The price is $306
Oct 5 - Oct 6
Total with taxes and fees
Newly renovated Farm cottage with Mountain views
A wooden cabin with a porch, a bench, and a table.

16. 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
$222 nightly
The price is $245
Oct 5 - Oct 6
Total with taxes and fees
Peaceful mountain cabin in charming Berryville VA - next to river and brewery
A bedroom with a bed, bedside table, lamp, and a window with curtains.

17. 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, (10 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.
$427 nightly
The price is $467
Oct 6 - Oct 7
Total with taxes and fees
Chalet w/Hot Tub, Deck, Game Room & EV Charger
A deck with a hot tub, wicker furniture, and a view of a green landscape.

18. Greek Spa - Frisbee Golf - Stone fire Pizza Oven

Greek Spa - Frisbee Golf - Stone fire Pizza Oven
Front Royal
$284 nightly
The price is $287
Oct 6 - Oct 7
Total with taxes and fees
Greek Spa - Frisbee Golf - Stone fire Pizza Oven
A single-story brick building with a front porch, a picnic table, and a barbecue grill.

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

Shenandoah River House | 3BR - Private Dock - Pets
Front Royal
$410 nightly
The price is $452
Oct 21 - Oct 22
Total with taxes and fees
Shenandoah River House | 3BR - Private Dock - Pets
A cozy living room with a grey sofa, patterned cushions, a small side table with a lamp, and decorative vases.

20. Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Front Royal
9.6 out of 10, Exceptional, (17 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
$205 nightly
The price is $226
Oct 4 - Oct 5
Total with taxes and fees
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
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

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

10/10 Excellent
"I always look forward to my stay here while traveling. Always a clean room and a friendly desk staff to greet you . Nice breakfast in the morning"
Joy 1-night trip
Posted 6 hours ago
Country Inn & Suites by Radisson, Winchester, VA

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $146 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.