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Compare 499 Vacation Homes in Winchester with updated reviews, rates, and availability.

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (143)
"Lovely setting and great property….."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Riverside cottage, minutes from historic Harpers Ferry; private river access!
9.8 out of 10, Exceptional, (56)
"Not much to say other than it was a great stay. Scott was super responsive for the few questions we had and everything was clean and comfortable."
The price is AED 533
AED 813 total
includes taxes & fees
6 Jun - 7 Jun
Riverside cottage, minutes from historic Harpers Ferry; private river access!
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
9.6 out of 10, Exceptional, (151)
"We enjoyed the home but the land even more. Nature is awesome!"
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
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Cozy Lakeside Homestead
10.0 out of 10, Exceptional, (166)
"Super close to the lake. Loved kayaking and fishing. Cozy property with everything you need all there. Truly enjoyed our stay."
The price is AED 771
AED 1,087 total
includes taxes & fees
4 Jun - 5 Jun
Cozy Lakeside Homestead
Riverfront Retreat
10.0 out of 10, Exceptional, (16)
"Location and property were beautiful, clean, and as described. Would recommend without hesitation and would stay again if we are ever back in the area."
Riverfront Retreat
Union Street Carriage Quarters
10.0 out of 10, Exceptional, (21)
"This was our third stay here in a short period of time as our house gets renovated. We just love its coziness & cleanliness. Great communication with owners. Highly recommend!"
Union Street Carriage Quarters
Secluded River Cabin Getaway (Masten Cabin)
9.8 out of 10, Exceptional, (128)
"This cabin was a wonderful place to stay! It was quiet except for the sound of birds in the woods. The interior of the cabin was clean and well furnished; the bed was especially comfortable. While we didn't make use of the fire pit, the screened porch was our favorite place to sit day or night. Although it might have been too early for them, we felt relaxed on the porch knowing we wouldn't be attacked by mosquitoes or other bugs. It was easy to take our dog out for a walk on the back roads...
Secluded River Cabin Getaway (Masten Cabin)
Warm, Welcoming Retreat on Shenandoah River and Stunning views
10.0 out of 10, Exceptional, (109)
"Look no further for your stay in the Shenandoah mountains. This gorgeous spot was so peaceful and serene.All you could hear were birds chirping, the rustling wind and river. There are kayaks, a fire pit, outdoor picnic tables and hammocks. It is a birding, hiking, and kayaking paradise. The house itself is beautifully decorated and each room was large, tasteful, and comfortable. The master bedroom was huge, comfortable and elegant. It had everything we needed including a large bathroom. The bed...
Warm, Welcoming Retreat on Shenandoah River and Stunning views
Hot Tub, Poker Table, River Access & Kayaks and Wineries
9.8 out of 10, Exceptional, (6)
"Everything was fine."
The price is AED 588
AED 1,539 total
includes taxes & fees
5 Jun - 6 Jun
Hot Tub, Poker Table, River Access & Kayaks and Wineries
Harpers Ferry Luxury, Spa Bathroom, Movie Room
9.6 out of 10, Exceptional, (9)
"It was a nice stay. The area is great for walking. The venue was nice, just very vertical! Great communication with the host."
The price is AED 716
AED 1,346 total
includes taxes & fees
23 Jun - 24 Jun
Harpers Ferry Luxury, Spa Bathroom, Movie Room
Historic gem in the heart of downtown Hamilton! Trees and a private stream
Historic gem in the heart of downtown Hamilton! Trees and a private stream
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (228)
"We hosted my friends bachelorette party and bridal shower with 14 people and it was a great time! The house was super clean and fit everyone comfortably. The hosts were immediate to respond to any messages!"
Breathtaking views with an indoor private pool, come escape with us
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (189)
"My family and I stayed with our dog at this beautiful cabin. It was spacious and decorated so nicely. Very cozy and relaxing atmosphere! We will definitely be back."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Charming Home with Yard Near Shenandoah River!
9.6 out of 10, Exceptional, (8)
"We had a good time at the place. The big kitchen table is perfect for gathering when the weather keeps you from the fabulous fire pit. We would go back if we had an occasion to."
Charming Home with Yard Near Shenandoah River!
Updated! Stunning country home near main street
10.0 out of 10, Exceptional, (33)
"The house is in a perfect location to visit the main attractions. Even the house is old, the kitchen and bathrooms were remodeled and the upper house was very clean. The house has a ping pong table in the basement but we didn't use it because the basement was very dirty."
The price is AED 547
AED 1,228 total
includes taxes & fees
6 Jun - 7 Jun
Updated! Stunning country home near main street
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
10.0 out of 10, Exceptional, (93)
"We enjoyed our stay at this historic home in the middle of town. We loved sitting on the porch and we slept great both nights."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
White House Inn - Historic Home in Harpers Ferry!
10.0 out of 10, Exceptional, (16)
"The house was so much more beautiful and bigger in person than I realized from photos! The location is such an easy walk down into town. The host checked in with me several times to make sure I was doing okay and didn't need anything. Would book again!"
The price is AED 1,190
AED 2,637 total
includes taxes & fees
13 Jun - 14 Jun
White House Inn - Historic Home in Harpers Ferry!
Eagle's Nest- A modern, pet friendly cabin on the river with a hot tub!
9.6 out of 10, Exceptional, (81)
"Really enjoyed the house."
Eagle's Nest- A modern, pet friendly cabin on the river with a hot tub!
River views, short walk to Harper Ferry, C&O Canal, and Appalachian trail.
8.8 out of 10, Excellent, (3)
"Comfortable stay. Has everything you need and more. Great backyard with swing-set, fire pit. Incredible sunset views overlooking the Potomac. Close to Harper’s Ferry, AT, Antietam, Boonsboro, C&O, walking, hiking, etc…"
River views, short walk to Harper Ferry, C&O Canal, and Appalachian trail.
Panorama Peak View- Million Dollar View!
Panorama Peak View- Million Dollar View!
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See all available properties in 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.

Other property types in Winchester

Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
9.8 out of 10, Exceptional, (244)
"We really enjoyed the property. It was clean. Internet worked well. Washer and dryer was nice. Too cold to enjoy the hot tub for me. My suggestions are a new shower head, thank goodness I didn’t have to wash my hair. The flow is too spread out and not enough to efficiently rinse as you shower. Second is a cheaper Kcup machine would be nice. Traveling with ground coffee is not really ideal for a quick trip away. Third thing I suggest is two beach towels (minimum) for the use of the hot tub. We...
The price is AED 367
AED 1,161 total
includes taxes & fees
4 Jun - 5 Jun
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Dreamtime - Modern A-frame Cabin w/ Hot tub
10.0 out of 10, Exceptional, (26)
"Cabin was amazing. Definitely would go back!"
Dreamtime - Modern A-frame Cabin w/ Hot tub
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (189)
"My family and I stayed with our dog at this beautiful cabin. It was spacious and decorated so nicely. Very cozy and relaxing atmosphere! We will definitely be back."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
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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