Winchester Holiday Rentals

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Holiday Rentals in Winchester

Canal Cabins

3.0 star property
9.4 out of 10, Exceptional, (6)
"Met a friend here after I had been camping/cycling the C&O from DC. Shower was great as were the facilities. Not too many places for a decent meal in town but we made do with the gas station pizza! "
The price is AU$218
includes taxes & fees
5 Aug - 6 Aug
Canal Cabins

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

10.0 out of 10, Exceptional, (377)
"We were a group of 6, including two children and absolutely loved the house, ammenities, and location. The hosts were great, and the check in super easy. Had a great stay and will definitely go back!"
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (45)
"We stayed here for our anniversary and had a great time. Hosts were very responsive when we had a question about the hot tub, "
The price is AU$585
includes taxes & fees
24 Aug - 25 Aug
Dreamtime - Modern A-frame Cabin w/ Hot tub

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (28)
"Very nice rest time…"
Charming Cabin in the Woods with River Access

Lookout Cabin in the mountains, Amazing Views!

9.8 out of 10, Exceptional, (17)
"Great spot - beautiful and laid back. Brian was very flexible which is greatly appreciated. "
The price is AU$540
includes taxes & fees
12 Aug - 13 Aug
Lookout Cabin in the mountains, Amazing Views!

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

10.0 out of 10, Exceptional, (39)
"The pictures for this cabin don't reflect how roomy and spacious this place is! It is a very clean, comfortable and quiet retreat. My wife and I had a fantastic stay and would not hesitate to book this place again if we are in the area.Thanks Patty and Bill for allowing us to stay at this wonderful place."
Private, light filled retreat space... with your own pickleball court!

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (325)
"This was absolutely just what we needed! The view was so breathtaking and the serenity of this place is to die for! I was very pleased with our stay here and we will definitely be returning de"
Star view cabin-Riverfront

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (125)
"Riverkeeper Inn is located in a peaceful and quiet area of Harpers Ferry, equally perfect in early mornings and late nights. The check-in and check-out process were very easy, and the property itself had everything we could've asked for, and then some."
RIVERKEEPER INN, Waterfront Property on the Potomac River

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

10.0 out of 10, Exceptional, (332)
"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

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

10.0 out of 10, Exceptional, (126)
"Spectacular location. Charming and comfortable. The steps can be a challenge but are worth the effort."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

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

2.0 star property
10.0 out of 10, Exceptional, (34)
"Plenty of space for 8 adults - fantastic rooms and beds. Really liked the secluded area - got to hear cows walk by in the morning!"
The price is AU$673
includes taxes & fees
5 Aug - 6 Aug
Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray

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

9.6 out of 10, Exceptional, (188)
"The highlight of the rental for us was definitely the property. We loved the view and our kids enjoyed wading in the river. Hot tub was great after days spent hiking in Shenandoah! "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

Outdoor Theatre | Hot Tub | Fire Pit | Dogs

9.8 out of 10, Exceptional, (47)
"This is the perfect place to stay! Very clean and cozy cabin that had everything we needed. Our host was super easy to work with and very responsive. My family and I enjoyed our perfect little getaway! "
The price is AU$502
includes taxes & fees
18 Aug - 19 Aug
Outdoor Theatre | Hot Tub | Fire Pit | Dogs

Falling Leaf Cabin - Rustic Charm With Modern Decor!

9.8 out of 10, Exceptional, (291)
"Great location! It provided the perfect space to unwind. I image the view changes with each season, but always beautiful with a feeling of privacy. "
Falling Leaf Cabin - Rustic Charm With Modern Decor!

Breathtaking View with an Indoor Pool

9.8 out of 10, Exceptional, (256)
"We really enjoyed our stay at Bear Chase Manor! Amazing property, great pool, in a beautiful area. We are already discussing possible future visits! "
Breathtaking View with an Indoor Pool

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (57)
"We truly loved this location and definitely will be back!"
The price is AU$224
includes taxes & fees
1 Sept - 2 Sept
❤️ Secluded 1940s Romantic Tiny House on the River

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (90)
"This beautiful cabin has everything you need for a wonderful stay. My husband and I stayed here for our 44th anniversary while visiting local wineries. It was a perfect location."
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

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

9.8 out of 10, Exceptional, (189)
"The cabin is an absolute gem, located in the mountains but within easy reach of groceries, restaurants, hiking, fishing, etc. The stay was spacious, clean, tidy, had plenty of entertainment options, and communication was timely. Would not hesitate to book again. "
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

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

10.0 out of 10, Exceptional, (321)
"This is, I believe, my fourth time staying at Solitude. I keep coming back because it is perfect. "
The price is AU$475
includes taxes & fees
19 Aug - 20 Aug
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Historical cottage in the town of Paris

9.8 out of 10, Exceptional, (45)
"This is a nice home near sky meadow park. A great place to see the stars... Very close to DC. "
Historical cottage in the town of Paris
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

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?

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!: This holiday home rental outside of Winchester is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of private gardens in this rental home to help you unwind.

How many holiday rentals will I find in Winchester?

Choose from 19 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.