Winchester Holiday Rentals

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Holiday Rentals in Winchester

Our top choices for Winchester holiday rentals

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 NZ$697
includes taxes & fees
29 Sept - 30 Sept
Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, 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 NZ$521
includes taxes & fees
29 Sept - 30 Sept
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

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 NZ$247
includes taxes & fees
25 Sept - 26 Sept
Road Haven 1830

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

Canal Cabins

3.0 star property
9.6 out of 10, Exceptional, (9)
"Very nice "
The price is NZ$238
includes taxes & fees
24 Sept - 25 Sept
Canal Cabins

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!

Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill

9.6 out of 10, Exceptional, (11)
"Hot tub was nice relaxing cozy cabin"
The price is NZ$310
includes taxes & fees
24 Sept - 25 Sept
Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill

Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

9.6 out of 10, Exceptional, (62)
"We had a great stay! The place was very clean, the back deck was such a great added bonus.. had a good selection of movies and games. 4 wheel drive is advisable. Very comfy!!"
The price is NZ$561
includes taxes & fees
1 Oct - 2 Oct
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

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!

Star view cabin-Riverfront

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

Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks

10.0 out of 10, Exceptional, (11)
"It was an amazing place, will recommend to friends and hopefully will be back."
The price is NZ$419
includes taxes & fees
30 Sept - 1 Oct
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks

Endless Skies & Spectacular Views!!!

10.0 out of 10, Exceptional, (76)
"Gorgeous property, very peaceful, highly recommended!"
Endless Skies & Spectacular Views!!!

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 NZ$743
includes taxes & fees
24 Sept - 25 Sept
Modern Glass Retreat in Fort Valley with WiFi, AC, EV charger

The Oculus - Huge Cabin with a Hot Tub!

9.6 out of 10, Exceptional, (24)
"This was a great place for our vacation."
The price is NZ$742
includes taxes & fees
2 Oct - 3 Oct
The Oculus - Huge Cabin with a Hot Tub!

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (61)
"We truly loved this location and definitely will be back!"
The price is NZ$180
includes taxes & fees
5 Oct - 6 Oct
❤️ Secluded 1940s Romantic Tiny House on the River

1959 TOPLEY Retreat offers Serenity/Tranquility + Pets - Fenced Area/ FREE WIFI

10.0 out of 10, Exceptional, (8)
"This is a lovely home and super clean. My partner and I stayed here for a long weekend to go hiking around Shenandoah. Luray was also a nice little town."
The price is NZ$481
includes taxes & fees
22 Oct - 23 Oct
1959 TOPLEY Retreat offers Serenity/Tranquility + Pets - Fenced Area/ FREE WIFI

Private Log Cabin - Hot Tub, NEW SatelliteWi-Fi, Fireplace, Sm Pet Considered

9.8 out of 10, Exceptional, (123)
"The property was awesome. Very secluded, very clean, fully stocked. Check in is a little late and check out a little early, but would definitely stay again. The property was incredible with only little things like the electric fireplaces or the bubbles on the hottub not working. Plenty of space for a whole family, and plenty to do if you bring dogs. "
Private Log Cabin - Hot Tub, NEW SatelliteWi-Fi, Fireplace, Sm Pet Considered

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

Peaceful Waterfall House -- 2 bedroom hidden treasure

9.8 out of 10, Exceptional, (7)
"What a nice, history rich house to stay in. You can tell it has old bones but has been maintained and is full of character. Loved the relaxing setting with the river running around the house. Plenty to explore on the property down by the water and in the woods. Exactly what’s needed for a relaxing get away. Close to town as well for anything needed. Kirsten was a great host. "
The price is NZ$539
includes taxes & fees
24 Sept - 25 Sept
Peaceful Waterfall House -- 2 bedroom hidden treasure

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.
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

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 favorite 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 depends 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 NZ$180 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 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.