Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Our top choices for Winchester holiday rentals

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

10.0 out of 10, Exceptional, (381)
"House had all we needed! "
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

Canal Cabins

3.0 star property
9.6 out of 10, Exceptional, (8)
"Very nice "
The price is €108
includes taxes & fees
31 Aug - 1 Sept
Canal Cabins

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 €193
includes taxes & fees
4 Sept - 5 Sept
Dreamtime - Modern A-frame Cabin w/ Hot tub

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

10.0 out of 10, Exceptional, (324)
"Loved the privacy "
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

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

9.8 out of 10, Exceptional, (192)
"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

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

10.0 out of 10, Exceptional, (41)
"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!

Outdoor Theatre | Hot Tub | Fire Pit | Dogs

9.8 out of 10, Exceptional, (50)
"It was a amazing stay"
The price is €260
includes taxes & fees
23 Sept - 24 Sept
Outdoor Theatre | Hot Tub | Fire Pit | Dogs

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

10.0 out of 10, Exceptional, (128)
"Place was nice and clean. Location was good. We enjoyed the quiet. Had a blast!"
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Family Farmhouse Inn

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
26 Aug - 27 Aug
Family Farmhouse Inn

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.4 out of 10, Exceptional, (126)
"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, (335)
"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

Breathtaking View with an Indoor Pool

9.8 out of 10, Exceptional, (258)
"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

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (92)
"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.

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (31)
"Very nice rest time…"
The price is €262
includes taxes & fees
28 Aug - 29 Aug
Charming Cabin in the Woods with River Access

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (326)
"My family loves Shenandoah NP and we’ve stayed at multiple places. This cabin was perfect for us! The views were amazing!"
Star view cabin-Riverfront

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

9.6 out of 10, Exceptional, (190)
"We had a great time sitting on the porch relaxing. "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

❤️ Secluded 1940s Romantic Tiny House on the River

9.8 out of 10, Exceptional, (60)
"We truly loved this location and definitely will be back!"
The price is €119
includes taxes & fees
1 Sept - 2 Sept
❤️ Secluded 1940s Romantic Tiny House on the River

Blue Ridge Getaway - Sunset Views, A.T. Access

10.0 out of 10, Exceptional, (55)
"My girlfriend and I had a wonderful weekend escaping the hustle and bustle of the city. The view was spectacular and the property was perfect!"
The price is €317
includes taxes & fees
2 Sept - 3 Sept
Blue Ridge Getaway - Sunset Views, A.T. Access

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

10.0 out of 10, Exceptional, (62)
"Location and house was just as described. Would highly recommend staying here if your looking for a location close to Harper's Ferry."
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

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

10.0 out of 10, Exceptional, (71)
"We had a great experience for a family wedding! The place was very clean and was in a great local spot that was easy to get to our wedding venue. "
The price is €269
includes taxes & fees
27 Aug - 28 Aug
Cottage by the Caverns *FIRE PIT* *MOUNTAIN 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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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?

Secluded Mountain Home Features Breathtaking Valley Views and 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 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.