Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Canal Cabins

3.0 star property
9.6 out of 10, Exceptional, (10)
"Very nice "
The price is €109
includes taxes & fees
12 Oct - 13 Oct
Canal Cabins

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (46)
"Awesome place! Perfect for 4 people. Great long weekend!"
Dreamtime - Modern A-frame Cabin w/ Hot tub

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

10.0 out of 10, Exceptional, (101)
"Clean and nice place to stay to visit Shenandoah "
The price is €389
includes taxes & fees
22 Oct - 23 Oct
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 €124
includes taxes & fees
21 Oct - 22 Oct
Road Haven 1830

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

9.8 out of 10, Exceptional, (286)
"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 €319
includes taxes & fees
14 Oct - 15 Oct
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

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

9.6 out of 10, Exceptional, (63)
"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 €281
includes taxes & fees
29 Oct - 30 Oct
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

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

10.0 out of 10, Exceptional, (50)
"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

9.0 out of 10, Wonderful, (12)
"Hot tub was nice relaxing cozy cabin"
The price is €189
includes taxes & fees
13 Oct - 14 Oct
Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill

Adorable river front cabin ,with hot tub on the River

9.0 out of 10, Wonderful, (9)
"Nice, clean little cabins with lots of amenities. Just a heads up, there's no cell service, so make sure you write down the code for the lockbox before you arrive. "
Adorable river front cabin ,with hot tub on the River

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (331)
"We had a wonderful time! The property has a great view and the host was very friendly and accommodating. "
Star view cabin-Riverfront

Endless Skies & Spectacular Views!!!

10.0 out of 10, Exceptional, (79)
"We had a great stay here. The home was comfortable, the views were nice, and everything was great!"
Endless Skies & Spectacular Views!!!

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

10.0 out of 10, Exceptional, (332)
"Place was beautiful and lived up to the name Solitude. Spent our honeymoon in perfect bliss. Great location to get away. "
The price is €251
includes taxes & fees
29 Oct - 30 Oct
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Bear Timbers log cabin on the Shenandoah River

9.8 out of 10, Exceptional, (67)
"We had a fantastic time! All messages were promptly answered and the property was clean and as advertised!"
Bear Timbers log cabin on the Shenandoah River

Falling Leaf Cabin - Rustic Charm With Modern Decor!

9.8 out of 10, Exceptional, (300)
"Cute cozy cabin in a great location. Was perfect for stopping in Luray, taking hiking trips to Shenandoah National Park, or just staying in. Had a wonderful time! Would definitely recommend to anyone looking for a cabin in the area."
Falling Leaf Cabin - Rustic Charm With Modern Decor!

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

10.0 out of 10, Exceptional, (340)
"We had a great time and can't wait to return"
The price is €280
includes taxes & fees
5 Nov - 6 Nov
"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, (200)
"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

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

10.0 out of 10, Exceptional, (75)
"This is a cute property with great proximity to Shenandoah National Park. The house had everything needed. The property owners provided excellent communication to make sure evertything was nice! Our time there was wonderful."
The price is €280
includes taxes & fees
29 Oct - 30 Oct
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

Hidden Gem in the woods with hot tub

9.6 out of 10, Exceptional, (82)
"Outstanding property was just what the doctor ordered for a rejuvenating time of R&R. Clean and comfortable, all of the amenities—including the hot tub— made for a lovely stay. "
Hidden Gem in the woods with hot tub

Outdoor Theatre | Hot Tub | Fire Pit | Dogs

9.8 out of 10, Exceptional, (55)
"It was a amazing stay"
The price is €318
includes taxes & fees
27 Oct - 28 Oct
Outdoor Theatre | Hot Tub | Fire Pit | Dogs

Peaceful Waterfall House -- 2 bedroom hidden treasure

9.6 out of 10, Exceptional, (9)
"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 €273
includes taxes & fees
20 Oct - 21 Oct
Peaceful Waterfall House -- 2 bedroom hidden treasure
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, apart-hotels, 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 €109 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. 

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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 17 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.