Winchester Holiday Rentals

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Holiday Rentals in Winchester

Secluded, Convenient, Hot tub, WiFi, Near Cacapon State Park

10.0 out of 10, Exceptional, (249)
"We stayed a weekend at the Chalet and highly recommend! The hot tub was amazing, beds were comfortable and the view was beautiful. It was a relaxing and thoroughly enjoyable trip"
Secluded, Convenient, Hot tub, WiFi, Near Cacapon State Park

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

10.0 out of 10, Exceptional, (363)
"The house was nice. There was everything that we needed for our stay. The view from the deck was beautiful. The bed was comfortable. The fireplace and hot tub were great"
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

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

9.8 out of 10, Exceptional, (47)
"This is close to the thornton gap entrance. With the shades open, it's a very sunny house. The house is right in the town of Luray, so you're close to your neighbors, but they're quiet. If possible, the owners should put a curtain in front of the front glass door."
The price is AU$514
includes taxes & fees
2 Mar - 3 Mar
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

Secluded Pet-Friendly High-Tech Log Cabin in the Woods

9.6 out of 10, Exceptional, (170)
"The cabin was very well appointed. All linens were provided, as well as plenty of spare cleaning products for dishes and laundry. The interior of the cabin was beautiful and well laid out. Unfortunately we had mainly rain while in town, so the technology played a large part for us. The town of Berkely Springs is 20 minutes away and is fantastic! With or without kids along, this is a great place to stay! "
Secluded Pet-Friendly High-Tech Log Cabin in the Woods

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (16)
"No central heating, bathroom fan couldn't be turned off, dinning room table light didn't work and front steps were not safe."
Charming Cabin in the Woods with River Access

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (51)
"It was a cozy little tiny house located right on the river. I came in January and it was about 15 degrees outside so I did not get to use the outdoor shower or grill. I was able to enjoy the view of the river from the tiny house and walk outside on the road (not too many cars). If it was any warmer I would have built a fire and sat outside closer to the river. I would love to come back and stay when it was warmer to enjoy the outdoor more. Perfect retreat to reset. Very close to a nearby college...
The price is AU$178
includes taxes & fees
17 Feb - 18 Feb
❤️ Secluded 1940s Romantic Tiny House on the River

Cottage w Hot Tub, Pond & Kayaks, Fire Pit, & WiFi

8.8 out of 10, Excellent, (30)
"Tony was an amazing host. The property was home-y and very spacious. Perfect place to accommodate 2 couples and 2 children (or adults who are children at heart). It was a nice little getaway in the woods with easy access to the town. If you’re looking for a place for some great R&R, this is your spot!"
The price is AU$417
includes taxes & fees
17 Feb - 18 Feb
Cottage w Hot Tub, Pond & Kayaks, Fire Pit, & WiFi

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

9.8 out of 10, Exceptional, (263)
"We look forward to coming back! The cabin was clean, comfortable, and the seclusion made it feel like we were the only people on earth ringing in the newyear. "
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

10.0 out of 10, Exceptional, (111)
"Great communication with host. Cosy house, well equipped kitchen in a great location."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (41)
"Our families decided to rent the property for a getaway close to the DMV. It was easy to check in, get around Charles Town and enjoy the property. Even with an unexpected 6" of snow, we still found time to appreciate everything the property had to offer."
Charles Town Home w/ Private Pool & Hot Tub

Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray

2.0 star property
10.0 out of 10, Exceptional, (19)
"The house couldn't have been better! The location was perfect, and the house had all the amenities and more. The views are gorgeous, and we hope to stay here again!!"
The price is AU$953
includes taxes & fees
18 Feb - 19 Feb
Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (35)
"The cabin was in a beautiful community and setting with a fabulous outdoor area facing the woods. Many amenities in the home that made our stay easy with nicely renovated interior. Owner was very willing and able to offer help with anything and was receptive to feedback. Thank you!"
The price is AU$601
includes taxes & fees
19 Feb - 20 Feb
Dreamtime - Modern A-frame Cabin w/ Hot tub

18th Century Stone Cottage minutes from historic Middleburg

10.0 out of 10, Exceptional, (35)
"We absolutely loved this little cottage. It's a great location near Middleburg, tucked back in the woods. It's got everything you need for a peaceful retreat. A perfect place to curl up in front of the fire with a book. The host was so welcoming and easy to work with. We'll definitely be back!"
The price is AU$629
includes taxes & fees
17 Feb - 18 Feb
18th Century Stone Cottage minutes from historic Middleburg

MID-CENTURY MODERN A-FRAME - HOT TUB/FIREPIT IN WOODS

10.0 out of 10, Exceptional, (13)
"Beautiful cozy cabin. It was clean and quiet. Took an awesome hike to the devil's nose, explored Berkeley springs all within a short distance of the cabin. Property owner was super helpful."
The price is AU$548
includes taxes & fees
3 Mar - 4 Mar
MID-CENTURY MODERN A-FRAME - HOT TUB/FIREPIT IN WOODS

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

10.0 out of 10, Exceptional, (304)
"Quiet and the hot tub was popular. Nice winter trip through Shen Nat Park, but no snowshoeing."
The price is AU$425
includes taxes & fees
17 Feb - 18 Feb
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

9.6 out of 10, Exceptional, (340)
"My friend and I spent the weekend in John's Cozy Cabin to enjoy some time away from our urban settings and focus on writing in a quiet, secluded place. This cabin was just what we were seeking because it was tranquil, isolated, in serene settings in the forest along the Shenandoah River, and it had everything we needed. John was proactive in his approach, taking the time to discuss our needs and preferences before our stay. His thorough communication and attention to detail ensured that my...
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

Cozy Getaway near Harper's Ferry, C&O & Potomac River, Frederick & train to DC

10.0 out of 10, Exceptional, (24)
"The apartment is perfectly located by the trail and coffee shop and a cute restaurant! "
The price is AU$256
includes taxes & fees
7 Feb - 8 Feb
Cozy Getaway near Harper's Ferry, C&O & Potomac River, Frederick & train to DC

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (304)
"We experienced the beauty of a mountain snowstorm and it was awesome! We enjoyed the gorgeous view sitting by the fireplace and feeling super cozy. Nina the owner was so thoughtful, checking on us, suggesting a good place for our car during the storm so that we wouldn’t get stuck when it came time to go home, even cleaning our car off for us! That was above and beyond—thank you, Nina. The cabin is as pictured and well appointed. We plan to return here. "
Star view cabin-Riverfront

Enjoy Secluded Starry Nights! Near Luray, HotTub, FastWiFi, Handicap, Fireplace

10.0 out of 10, Exceptional, (188)
"We had a great time celebrating New Years at the cabin. We made use of all amenities, said hi to the horses, and enjoyed our stay. "
Enjoy Secluded Starry Nights! Near Luray, HotTub, FastWiFi, Handicap, Fireplace

Rustic River Cabin, Charming Riverfront, Hottub, 2 Stone Fireplaces, Dock, Views

9.6 out of 10, Exceptional, (17)
"Lovely little cabin with a great hot tub right on the river. "
Rustic River Cabin, Charming Riverfront, Hottub, 2 Stone Fireplaces, Dock, Views
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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Other types of properties in Winchester you may be interested in

La Quinta Inn & Suites by Wyndham Winchester

2.5 star property
9.2 out of 10, Wonderful, (1804)
"Good"
The price is AU$181
includes taxes & fees
17 Feb - 18 Feb
La Quinta Inn & Suites by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 star property
8.2 out of 10, Very good, (1102)
"Absolutely wonderful experience. Exceptionally clean with very nice staff. "
The price is AU$116
includes taxes & fees
1 Mar - 2 Mar
Travelodge by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 star property
9.0 out of 10, Wonderful, (1123)
"GOOD"
The price is AU$131
includes taxes & fees
17 Feb - 18 Feb
Microtel Inn & Suites by Wyndham Winchester
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.

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?

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails: This holiday home rental outside of Winchester is located in the mountains, 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. Make the most of games in this rental home to help you unwind.

How many holiday rentals will I find in Winchester?

Choose from 21 Expedia holiday rentals in Winchester for a memorable holiday.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Rocking S Ranch are a couple of the 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 Jim Barnett Park.

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.