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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 656 Vacation Homes in Winchester with updated reviews, rates, and availability.

Charming mountaintop cabin with pool table and breathtaking views
Outdoor dining

Charming mountaintop cabin with pool table and breathtaking views

9.8 out of 10, Exceptional, (198)
"Expectations exceeded! Perfect for a wintery early spring getaway, hot tubbing in the snow watching the clouds coast overhead. The cabin itself is well heated and features a great sound system, a well equipped kitchen, multi-tiered decks, and a fantastic panoramic view of the river valley. I appreciated the quick & kind responses to my questions prior to visiting. The only piece of advice I have is to make sure you have your check in info downloaded prior to visiting because you will have to...
Charming mountaintop cabin with pool table and breathtaking views
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Property grounds

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

10.0 out of 10, Exceptional, (43)
"Townhome was in a very convenient location, nicely stocked, roomy, and very comfortable. Communication was fast, friendly and helpful. We came for a girls' weekend and left wanting to come back again soon! No complaints. We'd definitely stay here again and were happy to support a Veteran family!"
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Miscellaneous

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.8 out of 10, Exceptional, (92)
"We enjoyed a very comfortable stay. House was very clean and cozy. We were a little surprised by the close proximity to other homes, but other than that it was as described. Hosts were easy to communicate with and created a very welcoming space for us. Thank you! "
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Outdoor spa tub

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

9.6 out of 10, Exceptional, (173)
"We had an extremely relaxing stay. The area is gorgeous…loved being close to the water. We brought our dog and it was great to let him run and play and just be a dog. Did have a few issues with a few appliances, but the host was super quick to bring a new remote and coffee pot. All in all we would stay again!"
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
Terrace/patio

Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains

9.8 out of 10, Exceptional, (28)
"We had a great time visiting with family and getting our much needed rest and relaxation at your beautiful house. Thanks!"
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
Lovely home, wonderful location.
Exterior

Lovely home, wonderful location.

10.0 out of 10, Exceptional, (62)
"My daughter and I stayed in this charming little home. Decorated with a mix of modern and antiques . Very comfortable, quiet and walkable to the Main Street. Would definitely recommend. "
The price is AED 478
AED 915 total
includes taxes & fees
31 Mar - 1 Apr
Lovely home, wonderful location.
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Exterior detail

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

10.0 out of 10, Exceptional, (113)
"My husband and I thoroughly enjoyed staying in Harper's Ferry. It is a beautiful historic town with many sights to see. This house made it very convenient to have quick access to everything. It was especially useful for time management. We were able to complete our full itinerary that we had planned in advance."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Secluded River Cabin Getaway (Masten Cabin)
Miscellaneous

Secluded River Cabin Getaway (Masten Cabin)

9.8 out of 10, Exceptional, (145)
"My daughter and I plus dog stayed for a long weekend of hiking. Loved the cabin! Very cute, warm and perfect for the weekend getaway."
Secluded River Cabin Getaway (Masten Cabin)
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Property grounds

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

9.6 out of 10, Exceptional, (91)
"Great family stay! Highly recommend "
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Modern Country House on the Shenandoah River
Property grounds

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (31)
"This was a perfect long weekend stay for two families (4 adults, 4 kids). Comfortable, spacious, and well-equipped house on a beautiful property. Very responsive and helpful host. Would give 6 stars if I could. We hope to be back soon!"
Modern Country House on the Shenandoah River
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
Terrace/patio

5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine

9.8 out of 10, Exceptional, (47)
"With grandparents and 2 families with children, not only was the house perfect but the fenced yard was huge and spectacular. We didn’t use the hot tub, but there was plenty of good space for adults, too. We gathered for a family wedding, but the space enabled us to spend a few wonderful relaxing days with family we rarely see. Communication with Leora was prompt and accommodating. 5 stars all around! Thank you!"
5-bedroom Farmhouse In Heart Of Virginia Horse Country- Private Trail To Wine
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Outdoor dining

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

9.8 out of 10, Exceptional, (214)
"We came down for the weekend for our anniversary. Rainy weekend, but such a nice and relaxing time. The kitchen was incredibly well-stocked! We will probably be back. Thank you for opening your property to us."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Cottage on King | Charming Historic Leesburg Home
Terrace/patio

Cottage on King | Charming Historic Leesburg Home

9.4 out of 10, Exceptional, (49)
"Location is great for walking to old town Leesburg. Very busy streets though, keep that in mind. Neighbors and owner were nice and not a problem. Parking can be tight for a larger vehicle. But a Yukon fits. Weather was freezing while we were there (nothing anyone can do about that) so we were stuck inside for our stay). Would be a good stop to base out of to explore historic downtown Leesburg. "
The price is AED 683
AED 1,242 total
includes taxes & fees
31 Mar - 1 Apr
Cottage on King | Charming Historic Leesburg Home
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!
Aerial view

Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!

10.0 out of 10, Exceptional, (44)
"A home away from home! We had a fabulous stay - doing day hikes in the national park (Thornton Gap is an easy 30min drive) and spending family time cooking, playing games in the evenings. We appreciated all the nice details Diana arranged for our stay. So glad we chose this location! "
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Fridge, microwave, oven, stovetop

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

9.8 out of 10, Exceptional, (93)
"What a perfect home for our Thanksgiving celebration! There were so many rooms in which to spread out, the beds were comfortable, and the location was central to necessities. We had a great stay!"
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

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

9.8 out of 10, Exceptional, (176)
"Very nice cabin, loved the covered porch. Great place to get in touch with nature. Nice trail right behind house"
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Beautiful Log Chalet/Cabin with Hot Tub
Smart TV, fireplace, DVD player, computer

Beautiful Log Chalet/Cabin with Hot Tub

10.0 out of 10, Exceptional, (64)
"Beautiful Cabin!"
Beautiful Log Chalet/Cabin with Hot Tub
The Lodge at Bear Rock
Smart TV, fireplace, video games, foosball

The Lodge at Bear Rock

The Lodge at Bear Rock
Charles Town Home w/ Private Pool & Hot Tub
Pool

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (41)
"Our families decided to rent the property for a getaway close to the DMV. It was easy to check in, get around Charles Town and enjoy the property. Even with an unexpected 6" of snow, we still found time to appreciate everything the property had to offer."
Charles Town Home w/ Private Pool & Hot Tub
Waterfront property in Harpers Ferry - Private River Access
Property grounds

Waterfront property in Harpers Ferry - Private River Access

10.0 out of 10, Exceptional, (23)
"Comfortable beds, lots of room, beautiful river location. Close to Harper’s Ferry, Antietam, walking/hiking trails. Very quiet neighborhood. Cozy electric fireplace and rec room downstairs. We were able to check in an hour early. Great family house!"
Waterfront property in Harpers Ferry - Private River Access
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 property types in Winchester

Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (307)
"I recently stayed at this cabin over the weekend, and it was an unforgettable experience. The views were absolutely breathtaking — whether it was sunrise over the mountains or relaxing in the evening with a stunning sunset, the scenery was incredible from every angle.The cabin itself was just as impressive. It was beautifully designed, immaculately clean, and had all the comforts of home. From cozy furniture to thoughtful amenities, everything was perfect. The peaceful surroundings made it the...
Star view cabin-Riverfront
Dreamtime - Modern A-frame Cabin w/ Hot tub
Outdoor dining

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (36)
"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 AED 1,062
AED 1,302 total
includes taxes & fees
24 Apr - 25 Apr
Dreamtime - Modern A-frame Cabin w/ Hot tub
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
Smart TV, DVD player, books, video library

Cozy Mountain Cabin w/ Steam Shower! Great for Couples.

10.0 out of 10, Exceptional, (59)
"The cabin was beautiful! Brigid has the cabin well stocked. She was very welcoming. Our family with kids and a dog felt very comfortable and even pampered!"
The price is AED 569
AED 1,248 total
includes taxes & fees
31 Mar - 1 Apr
Cozy Mountain Cabin w/ Steam Shower! Great for Couples.
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.