Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

9.8 out of 10, Exceptional, (174)
"The location was exactly what we needed and wanted. If you want to totally relax, get semi off the grid, this is your place. Take a hike and take it all in. Thank you to our hosts for making such a great property available."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

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

10.0 out of 10, Exceptional, (248)
"We had a really great weekend at the Chalet! This was the 1st time our group of guys had gotten together since the pandemic and it was great to just sit around the upstairs fireplace and catch up. The dining table was great for meals and board games. Plenty of beds and bedrooms as well. The hot tub was perfect!"
The price is €832
includes taxes & fees
30 Jan - 31 Jan
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, (362)
"I recently stayed at this vacation rental and had a pleasant experience. The check-in process was simple. Just a heads-up, the drive to the house is a bit narrow in some spots, adding a touch of adventure to your journey! The property itself is well-maintained. The rooms are well-equipped, providing necessary amenities for a comfortable stay. The kitchen is functional with basic appliances and essentials, making meal preparation convenient. The views from the living area and front bedrooms are...
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

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

9.8 out of 10, Exceptional, (46)
"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 €320
includes taxes & fees
23 Feb - 24 Feb
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

9.8 out of 10, Exceptional, (211)
"Highly recommend staying here. We even had a little snow! Family friendly and cozy. "
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

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

9.6 out of 10, Exceptional, (169)
"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

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (34)
"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 €368
includes taxes & fees
26 Feb - 27 Feb
Dreamtime - Modern A-frame Cabin w/ Hot tub

White House Inn - Historic Home in Harpers Ferry!

10.0 out of 10, Exceptional, (27)
"Great location in a very safe neighborhood! House was very roomy with very comfy beds. Would definitely stay here again!! "
The price is €477
includes taxes & fees
30 Jan - 31 Jan
White House Inn - Historic Home in Harpers Ferry!

❤️ 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 €109
includes taxes & fees
4 Feb - 5 Feb
❤️ Secluded 1940s Romantic Tiny House on the River

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

9.0 out of 10, Wonderful, (29)
"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 €255
includes taxes & fees
3 Feb - 4 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.

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (41)
"Lots of space for everyone, excellent pool and hot tub"
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 €582
includes taxes & fees
2 Feb - 3 Feb
Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray

The Perch Riverfront Cabin - Starlink Satellite Wi-Fi

9.4 out of 10, Exceptional, (29)
"Great getaway with 2 adults, tween and child. There was enough room for all. The nook was a hit with the kids. The area was very quiet and relaxing. It snowed while we were there and the roads were plowed fast. House was very clean and well stocked. There was plenty of cookware and spices available. Would definitely come back. "
The Perch Riverfront Cabin - Starlink Satellite Wi-Fi

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 €386
includes taxes & fees
30 Jan - 31 Jan
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 €339
includes taxes & fees
13 Feb - 14 Feb
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, (302)
"We had a wonderful and recuperative weekend at Solitude. We especially enjoyed the hot tub and the fireplace. Perfect!"
The price is €259
includes taxes & fees
4 Feb - 5 Feb
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

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 €157
includes taxes & fees
6 Feb - 7 Feb
Cozy Getaway near Harper's Ferry, C&O & Potomac River, Frederick & train to DC

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

9.6 out of 10, Exceptional, (339)
"This cabin stay was wonderful. It is perched high on a cliff and the views are spectacular. The cabin is secluded which makes for a nice relaxing stay. I can't wait to come back."
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
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, (1796)
"Nice clean place"
The price is €103
includes taxes & fees
9 Feb - 10 Feb
La Quinta Inn & Suites by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 star property
8.2 out of 10, Very good, (1099)
"Tout est très bien a proximités de plein de chose restaurant costco et plusieurs autre .je le recommande. "
The price is €67
includes taxes & fees
30 Jan - 31 Jan
Travelodge by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 star property
9.0 out of 10, Wonderful, (1119)
"Peaceful and relaxing"
The price is €79
includes taxes & fees
6 Feb - 7 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 Nalls Farm Market 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 Apple Blossom Mall.

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.