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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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 CA $209
CA $367 total
includes taxes & fees
Sep 27 - Sep 28
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 CA $155
CA $272 total
includes taxes & fees
Sep 27 - Sep 28
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 CA $116
CA $363 total
includes taxes & fees
Sep 28 - Sep 29
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 CA $195
CA $329 total
includes taxes & fees
Sep 27 - Sep 28
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.
The price is CA $251
CA $455 total
includes taxes & fees
Oct 4 - Oct 5
Morocco Loft 2BR overlooking city walking mall
A living room with a sofa, armchair, coffee table, and a television.

6. 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 CA $261
CA $473 total
includes taxes & fees
Sep 27 - Sep 28
Nostalgia Lane in the heart of the city
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.
The price is CA $275
CA $351 total
includes taxes & fees
Sep 27 - Sep 28
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.

8. 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 CA $279
CA $497 total
includes taxes & fees
Sep 27 - Sep 28
Cameron Charmer pristine downtown apt with double master suites
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 Stock Exchange downtown 3rd floor studio apt
A white building with a black door and a set of blue-painted stairs with black railings.

10. 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 CA $162
CA $272 total
includes taxes & fees
Sep 30 - Oct 1
The Blue Door steps from Handley Library
A hot tub in front of a wooden cabin with a tree in the background.

11. 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 CA $204
CA $245 total
includes taxes & fees
Sep 28 - Sep 29
Luxury tiny home farm stay on historic property with hot tub in Stephens City
A compact kitchen with a central island, wooden cabinets, a microwave, and a refrigerator.

12. Buena Vista

Buena Vista
Shawneeland
10.0 out of 10, Exceptional, (1 review)
The price is CA $130
CA $309 total
includes taxes & fees
Sep 29 - Sep 30
Buena Vista
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.
The price is CA $289
CA $521 total
includes taxes & fees
Oct 4 - Oct 5
WonderClock House downtown vintage duplex w/ porches, steps to Handley Library
A garden with a wooden swing set and a circular seating area.

14. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (50 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 CA $203
CA $431 total
includes taxes & fees
Sep 27 - Sep 28
Newly renovated Farm cottage with Mountain views
A hot tub with a view of a forest and a sunset.

15. 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.
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
A living room with a sofa, a coffee table, a fireplace, a television, and a dining area in the background.

16. 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 CA $313
CA $559 total
includes taxes & fees
Sep 27 - Sep 28
Scarborough Fair walk to downtown two story apt
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

17. Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (44 reviews)
"Beautiful, relaxing and quiet cabin, exceeded expectations."
United States
Johnathan B.
The price is CA $241
CA $300 total
includes taxes & fees
Sep 27 - Sep 28
Blue Mountain Cabin, secluded, perfect for couples, near main road
A modern kitchen with white cabinets, stainless steel appliances, and a central island with stools.

18. Frisbee golf • Private Acreage • Stonefire pizza

Frisbee golf • Private Acreage • Stonefire pizza
Front Royal
7.6 out of 10, Good, (4 reviews)
"The place was clean and bed was comfortable. Check in was a breeze. The hot tub was a great addition! The property is secluded with a large yard. Kitchen was great for our anniversary dinner."
United States
Katie
Frisbee golf • Private Acreage • Stonefire pizza
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, (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.
The price is CA $414
CA $712 total
includes taxes & fees
Oct 7 - Oct 8
Chalet w/Hot Tub, Deck, Game Room & EV Charger
A modern kitchen with stainless steel appliances, a built-in oven, and a microwave.

20. 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 CA $265
CA $494 total
includes taxes & fees
Oct 18 - Oct 19
Dragonfly Inn II Fabulous 2BR 1BA modern downtown apt walk to everything
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

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent
"great ,good price"
Michael 2-night trip
Posted 2 hours ago
Fairfield Inn & Suites by Marriott Winchester

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester vacation rentals we have selected for you start as low as CA $187 per night. Entering your travel dates in the search wizard 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.