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

Charming mountaintop cabin with hot tub, pool table, and breathtaking views

9.8 out of 10, Exceptional, (197)
"We booked the cabin for a weekend get away. The cabin was great. My boyfriend purposed to me and I left the ring at the cabin! Please contact me ASAP! "
Charming mountaintop cabin with hot tub, pool table, and breathtaking views

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

9.8 out of 10, Exceptional, (91)
"The place is so beautiful and so peaceful the views to the river are amazing. We are planing to visit again. We had an excellent time with my friends. Thank you again Scott and Margie. "
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

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

Trailside Retreat in breathtaking Western Loudoun

10.0 out of 10, Exceptional, (44)
"We had a full family 4 day retreat and Jill’s place was perfect. Lots of room, beds were so comfy and contained all the kitchen and bathroom supplies we needed. Everything was clean - they even had some toys for the kids. Great location…convenient to all activities, restaurants and hiking trails. We would definitely book again. 5 stars!"
Trailside Retreat in breathtaking Western Loudoun

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

9.8 out of 10, Exceptional, (123)
"We traveled with a couple who are good friends to celebrate my upcoming birthday. Visiting Harpers Ferry in the winter was a good decision, because it wasn't crowded yet most everything was open. Breweries and wineries and museums. . . it was a great trip! The home is beautiful and very thoughtfully restored. The owner even won a preservation award for the house and it's richly deserved! The kitchen is well stocked and everything was just comfortable. It was a great place from which to explore...
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Secluded River Cabin Getaway (Masten Cabin)

9.8 out of 10, Exceptional, (143)
"This cabin & the listing description is exactly what you get. Remote & quiet. My dogs were in heaven with all the space to run in the woods. Hubby gathered firewood, which there was .plenty very close by "
Secluded River Cabin Getaway (Masten Cabin)

1805 Farmhouse with Heated Pool in Harpers Ferry

10.0 out of 10, Exceptional, (37)
"The house and property were absolutely perfect for our group. Lots of privacy, the renovations are very well done. All technology is top of the line and works as expected. The pool, or in our case hot tub, was even better than we expected. It was used both nights we were there. The barn apartment is a wonderful place for some additional privacy from a large group, and is extremely comfortable. We would recommend this house 100%. "
1805 Farmhouse with Heated Pool in Harpers Ferry

Riverfront Retreat

10.0 out of 10, Exceptional, (27)
"We made a great choice in choosing the Riverfront Retreat for our Thanksgiving celebration. The large dining table fit our group and its close proximity to the kitchen made serving and cleanup a breeze. One bedroom is set apart from the others which worked perfectly for one couple who ducked out at 5am to catch a flight out of Dulles (about an hours drive) without disturbing others in the group. We enjoyed hiking in Seven Bends State Park and even toured the Shenandoah Caverns (a short drive)....
Riverfront Retreat

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

Historic Hideaway

10.0 out of 10, Exceptional, (14)
"We had a wonderful stay at Janelle’s cottage in Leesburg. Every possible detail and amenity has been well thought out and provided. Janelle is an amazing host and very responsive. The fenced in back yard was great for our little fur baby. The beds were cozy and comfortable. The water pressure in the shower was wonderful. This is our new home away from home when we visit our daughter in Ashburn."
The price is SAR 563
SAR 1,191 total
includes taxes & fees
19 Mar - 20 Mar
Historic Hideaway

Modern Home on Middleburg Equestrian Farm

10.0 out of 10, Exceptional, (11)
"We had a lovely girls weekend away in this modern home tucked away in Middleburg. It was conveniently located near town and among rolling roads of horse country. The house was cosy, comfortable and had all the amenities of home. We especially liked the comf beds and Nespresso machine. "
Modern Home on Middleburg Equestrian Farm

Beautiful Log Chalet/Cabin with Hot Tub

10.0 out of 10, Exceptional, (65)
"Beautiful Cabin!"
Beautiful Log Chalet/Cabin with Hot Tub

Waterfront Log Home Hot Tub Flat yard w/ Volleyball Fire Pit & Tubes for Floating

9.2 out of 10, Wonderful, (23)
"location by the river was beautiful. House is roomy and great for our family of 12. "
The price is SAR 1,123
SAR 2,484 total
includes taxes & fees
12 Mar - 13 Mar
Waterfront Log Home Hot Tub Flat yard w/ Volleyball Fire Pit & Tubes for Floating

Walk to Historic Harpers Ferry! Beautiful Views.

10.0 out of 10, Exceptional, (42)
"Harper's Ferry is the perfect in between for our Mom's getaway, and we wanted enough room in case we recruited more. The house is great, basics are provided, and we were very comfortable! We will definitely keep it in mind for future trips!!"
Walk to Historic Harpers Ferry! Beautiful Views.

Fall Getaway on the Shenandoah River near Luray, VA highspeed WiFi

9.8 out of 10, Exceptional, (34)
"Jennifer is excellent to communicate with and the home is exactly as described. Our family of 9 enjoyed the quiet, the time together, and yes, even time on the river during Thanksgiving week again. Thanks again!"
Fall Getaway on the Shenandoah River near Luray, VA highspeed WiFi

Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

10.0 out of 10, Exceptional, (9)
"The house is well maintained and furnished, and the outdoor space is lovely. We had a great weekend in Leesburg and would come again. "
The price is SAR 525
SAR 1,325 total
includes taxes & fees
13 Mar - 14 Mar
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries

10.0 out of 10, Exceptional, (6)
"Stayed with my three daughters for a Galentine’s weekend and had a great time! Enjoyed some of the nearby hiking trails and soaked up the quiet beauty of the area."
#CozyCleanCabin#HotTub#WoodStove#PetsOK#near BMLodge&Skyline D&Wineries

BEST LOCATION: Historic Shepherdstown Getaway

10.0 out of 10, Exceptional, (80)
"We enjoyed being in town and an easy walk to shops and restaurants. The house is very large and can accommodate a good size group. Amy is a friendly and helpful host. We found the house to have a bit of an awkward layout and rather dark except for the front bedroom and living area. Our sense is that the kitchen and bathrooms could use updating"
BEST LOCATION: Historic Shepherdstown Getaway

Gruner Bungalow at Otium Cellars

9.8 out of 10, Exceptional, (95)
"Spacious, lovely, home that was perfect for 50th bday celebration with 8 women!"
Gruner Bungalow at Otium Cellars

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
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

9.8 out of 10, Exceptional, (306)
"We had a wonderful time enjoying this peaceful setting. The house is just as described and everything worked well! "
Star view cabin-Riverfront

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

9.6 out of 10, Exceptional, (342)
"Amazing view, and very quiet. Exactly what i was looking for. "
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

Heaven's Hideaway- a perfect getaway near the Shenandoah River!

9.6 out of 10, Exceptional, (100)
"The property was beautiful and the attention to detail was amazing. It made my wife and I want to build our own cabin based on this one. The location was serene but very close to some nice attractions in the area. My wife did get frightened by an animal when she went to grab something from the car. She couldn't identify what it was in the dark but do a bit of research on the local wildlife so that you aren't surprised like she was. Definitely would stay again."
Heaven's Hideaway- a perfect getaway near 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.