Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Winchester vacation rentals

A modern living room with a sofa, a coffee table, and a lamp. There is a kitchen area in the background with cabinets and a painting on the wall.

1. Executive Suites

Executive Suites
3.0 star property
Winchester
The price is CA $354
CA $401 total
includes taxes & fees
Nov 20 - Nov 21
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 CA $207
CA $341 total
includes taxes & fees
Nov 23 - Nov 24
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.

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.
The price is CA $154
CA $251 total
includes taxes & fees
Nov 12 - Nov 13
Rosamond nice downtown studio apt
A modern kitchen with stainless steel appliances, white cabinetry, and a central island.

4. 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 $105
CA $315 total
includes taxes & fees
Nov 16 - Nov 17
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.

5. 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 $193
CA $316 total
includes taxes & fees
Nov 15 - Nov 16
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
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 CA $250
CA $424 total
includes taxes & fees
Nov 15 - Nov 16
Morocco Loft 2BR overlooking city walking mall
A two-story house with a front porch, a mailbox, and a number plate.

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 CA $278
CA $472 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $203
CA $236 total
includes taxes & fees
Nov 19 - Nov 20
Luxury tiny home farm stay on historic property with hot tub in Stephens City
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 CA $154
CA $256 total
includes taxes & fees
Nov 16 - Nov 17
The Stock Exchange downtown 3rd floor studio apt
A wooden deck with white railings and a covered porch area.

10. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (49 reviews)
"Very cute and clean home. The location was great and Vanessa was awesome to work with"
United States
Diedra
The price is CA $189
CA $287 total
includes taxes & fees
Nov 9 - Nov 10
Mountain View Bungalow in Front Royal
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
8.8 out of 10, Excellent, (21 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 $259
CA $449 total
includes taxes & fees
Nov 9 - Nov 10
Nostalgia Lane in the heart of the city
A modern, dark-colored triangular building with a balcony and outdoor seating area.

12. 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 CA $270
CA $524 total
includes taxes & fees
Nov 30 - Dec 1
Chalet w/Hot Tub, Deck, Game Room & EV Charger
A lakeside property with a dock, a wooden deck, and a house surrounded by dense greenery.

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

Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
Front Royal
10.0 out of 10, Exceptional, (2 reviews)
"The gravel road to get to the properly is an adventure. The owner described it perfectly."
United States
Denise A.
The price is CA $194
CA $526 total
includes taxes & fees
Nov 9 - Nov 10
Shenandoah River House | Private River Dock, Pet Friendly | 3BR, Sleeps 6
A cozy living room with a grey sofa, patterned cushions, a small side table with a lamp, and decorative vases.

14. 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
9.0 out of 10, Wonderful, (18 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
The price is CA $208
CA $287 total
includes taxes & fees
Nov 9 - Nov 10
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
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, (57 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 $224
CA $438 total
includes taxes & fees
Nov 29 - Nov 30
Newly renovated Farm cottage with Mountain views
A house with a fire pit in the foreground and a deck with string lights in the background.

16. 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, (19 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 CA $301
CA $662 total
includes taxes & fees
Nov 9 - Nov 10
The Haven at Turkey Run | Hot Tub, Creek + Disc Golf on 13 Acres | 3BR, Sleeps 6
A spacious living room with a fireplace, a dining area with a bench, and a large sliding glass door leading to an outdoor patio.

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, (8 reviews)
"Great little hideout! We loved this little place, accurately described and the communication was superb!"
United States
P H.
The price is CA $196
CA $521 total
includes taxes & fees
Nov 16 - Nov 17
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
A wooden staircase leading to a deck with a lattice railing, surrounded by dense foliage.

18. 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, (47 reviews)
"Nice cabin for couples. The bed was comfy and had all basic necessities for making meals. We will definitely stay again."
United States
Carla M.
The price is CA $294
CA $337 total
includes taxes & fees
Nov 9 - Nov 10
Blue Mountain Cabin, secluded, perfect for couples, near main road
A two-story house with a balcony, surrounded by trees and snow.

19. Cozy A frame cabin in quaint Front Royal. Dog friendly

Cozy A frame cabin in quaint Front Royal. Dog friendly
Front Royal
9.4 out of 10, Exceptional, (11 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
The price is CA $203
CA $360 total
includes taxes & fees
Nov 11 - Nov 12
Cozy A frame cabin in quaint Front Royal. Dog friendly
An outdoor dining area with a wooden deck, a table set for four, and a view of the surrounding greenery.

20. NEW! Greek Spa - Frisbee Golf - Stonefire Pizza

NEW! Greek Spa - Frisbee Golf - Stonefire Pizza
Front Royal
The price is CA $114
CA $392 total
includes taxes & fees
Nov 16 - Nov 17
NEW! Greek Spa - Frisbee Golf - Stonefire Pizza
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

A Comfort Inn & Suites building with a modern design, featuring a prominent logo on the facade, a covered entrance, and multiple windows.
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
Winchester

10/10 Excellent

Nice quiet clean
Canada
Fay
Reviewed February 8, 2024
Comfort Inn & Suites 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 $105 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.

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.

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