Holiday Rentals in Winchester

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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 €122
includes taxes & fees
7 Aug - 8 Aug
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 €337
includes taxes & fees
24 Aug - 25 Aug
Dreamtime - Modern A-frame Cabin w/ Hot tub

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (324)
"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

"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, (125)
"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!

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

10.0 out of 10, Exceptional, (68)
"Sweet l, well located property with everything you need for a stay! "
The price is €292
includes taxes & fees
3 Aug - 4 Aug
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

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!

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (28)
"Very nice rest time…"
The price is €279
includes taxes & fees
23 Aug - 24 Aug
Charming Cabin in the Woods with River Access

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.

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 €359
includes taxes & fees
12 Aug - 13 Aug
Lookout Cabin in the mountains, Amazing Views!

Cozy Bear Cottage! New Furniture & Lamps/Fans!

10.0 out of 10, Exceptional, (64)
"We enjoyed our stay in this cabin. Lots of fun hiking in the National Park nearby. We loved sitting by the firepit in the evenings. The cabin was very clean and well-stocked with everything we needed. "
Cozy Bear Cottage! New Furniture & Lamps/Fans!

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

Riverfront🏕A-Frame/HOT TUB/Fire Pit! FAST Wifi

9.8 out of 10, Exceptional, (59)
"Great location beautiful place"
Riverfront🏕A-Frame/HOT TUB/Fire Pit! FAST Wifi

Family Farmhouse Inn

3.0 star property
9.6 out of 10, Exceptional, (35)
"Great place to stay! It’s clean cozy and quiet! I would definitely stay again in the future!"
The price is €125
includes taxes & fees
6 Aug - 7 Aug
Family Farmhouse Inn

Beautiful Private Cabin, adjacent to the National Forest

9.8 out of 10, Exceptional, (129)
"Peaceful and wonderful. Well appointed and very clean"
Beautiful Private Cabin, adjacent to the National Forest

Private Log Cabin - Hot Tub, NEW SatelliteWi-Fi, Fireplace, Sm Pet Considered

9.8 out of 10, Exceptional, (120)
"Peaceful, quiet, remote retreat. Enjoyed the hot tub and the beds were comfy. Walked around town and bought some treasures from the antique stores. Would recommend and will stay again."
Private Log Cabin - Hot Tub, NEW SatelliteWi-Fi, Fireplace, Sm Pet Considered

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!

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

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

9.8 out of 10, Exceptional, (273)
"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 €272
includes taxes & fees
13 Aug - 14 Aug
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River

9.2 out of 10, Wonderful, (232)
"Quiet, cozy cabin in serene setting. "
Rustic 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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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.