Winchester Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Winchester

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

10.0 out of 10, Exceptional, (98)
"Clean and nice place to stay to visit Shenandoah "
The price is AU$624
includes taxes & fees
21 Sept - 22 Sept
Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

Road Haven 1830

3.0 star property
9.6 out of 10, Exceptional, (36)
"Great place to stay! It’s clean cozy and quiet! I would definitely stay again in the future!"
The price is AU$219
includes taxes & fees
21 Sept - 22 Sept
Road Haven 1830

Falling Leaf Cabin - Rustic Charm With Modern Decor!

9.8 out of 10, Exceptional, (297)
"Well kept cabin in a secluded part of Shenandoah. Would book again!"
Falling Leaf Cabin - Rustic Charm With Modern Decor!

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (46)
"We stayed here for our anniversary and had a great time. Hosts were very responsive when we had a question about the hot tub, "
Dreamtime - Modern A-frame Cabin w/ Hot tub

Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

9.8 out of 10, Exceptional, (283)
"Very nice stay. We used the fire pit and hot tub and enjoyed both. Excellent location close to cacapon, we ended up hiking and doing the clay shooting. The cabin itself was very nice, cozy, and clean. "
The price is AU$459
includes taxes & fees
29 Sept - 30 Sept
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Private, light filled retreat space... with your own pickleball court!

10.0 out of 10, Exceptional, (47)
"Couldn't ask for a nicer place to stay peaceful, quiet with a great view. Wildlife is abundant and beautiful everything that you could need or want to relax Bill and Patty were excellent hosts looking forward to visiting again"
Private, light filled retreat space... with your own pickleball court!

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (93)
"Very nice relaxing getaway, quite how do you spell quiet and serene location. "
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

10.0 out of 10, Exceptional, (336)
"we were looking for a quiet get away, loved having our 16YO boy more interested in fishing and hiking then sitting on his Xbox! We all really loved how quiet and calm it was, definitely plan on going back"
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

9.6 out of 10, Exceptional, (196)
"We loved everything about our stay. The views were spectacular and the setting was so tranquil. "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

10.0 out of 10, Exceptional, (327)
"Place was beautiful and lived up to the name Solitude. Spent our honeymoon in perfect bliss. Great location to get away. "
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Canal Cabins

3.0 star property
9.6 out of 10, Exceptional, (9)
"Perfect for an over night Clean quiet simple. Ac needs repair"
The price is AU$209
includes taxes & fees
21 Sept - 22 Sept
Canal Cabins

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (330)
"Great location, great views, "
Star view cabin-Riverfront

Spectacular Views, Swimming Pool, Hot Tub, Real Log Fires, Mountain Getaway

9.4 out of 10, Exceptional, (144)
"Enjoyable. 4wd required"
Spectacular Views, Swimming Pool, Hot Tub, Real Log Fires, Mountain Getaway

Modern Glass Retreat in Fort Valley with WiFi, AC, EV charger

10.0 out of 10, Exceptional, (6)
"This was a perfect weekend get away! Super clean. The host provided all the necessities that you might need like shampoo, soap, tissues, etc. The host was very prompt with responding to questions. Would definitely recommend! "
The price is AU$647
includes taxes & fees
21 Sept - 22 Sept
Modern Glass Retreat in Fort Valley with WiFi, AC, EV charger

Mountain Views, River Frontage & HotTub + Country!

9.8 out of 10, Exceptional, (31)
"Great location and beautiful property. "
Mountain Views, River Frontage & HotTub + Country!

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

10.0 out of 10, Exceptional, (74)
"Perfect for hiking trails along Skyline Drive. Luray is a cute town with plenty to do nearby."
The price is AU$470
includes taxes & fees
21 Sept - 22 Sept
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

The Oculus - Huge Cabin with a Hot Tub!

9.6 out of 10, Exceptional, (23)
"This was a great place for our vacation."
The price is AU$667
includes taxes & fees
2 Oct - 3 Oct
The Oculus - Huge Cabin with a Hot Tub!

Blue Ridge Getaway - Sunset Views, A.T. Access

10.0 out of 10, Exceptional, (57)
"My girlfriend and I had a wonderful weekend escaping the hustle and bustle of the city. The view was spectacular and the property was perfect!"
The price is AU$556
includes taxes & fees
24 Sept - 25 Sept
Blue Ridge Getaway - Sunset Views, A.T. Access

❤️ Secluded 1940s Romantic Tiny House on the River

9.8 out of 10, Exceptional, (60)
"We truly loved this location and definitely will be back!"
The price is AU$165
includes taxes & fees
2 Oct - 3 Oct
❤️ Secluded 1940s Romantic Tiny House on the River

Outdoor Theatre | Hot Tub | Fire Pit | Dogs

9.8 out of 10, Exceptional, (53)
"It was a amazing stay"
The price is AU$489
includes taxes & fees
30 Sept - 1 Oct
Outdoor Theatre | Hot Tub | Fire Pit | Dogs
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

Find out more about Winchester

Find out more about Winchester

Everything you need to know about Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winchester holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as AU$165 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday 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 holiday.

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 holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Shenandoah Valley Discovery Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theatre scene while you're visiting.

What are some of the best holiday rentals that Winchester has to offer?

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub: This holiday home rental outside of Winchester is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Winchester?

Choose from 16 Expedia holiday rentals in Winchester for a memorable holiday.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Nalls Farm Market are a couple of the family-friendly sights, whereas cultural attractions include Bright Box Theater and Winchester Little Theater. Other places in town to visit include Patsy Cline Historic House and Museum of the Shenandoah Valley.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family getaway.