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

Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

9.2 out of 10, Wonderful, (17)
"We had a great time "
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

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

10.0 out of 10, Exceptional, (122)
"Great location, loved the "
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

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

9.6 out of 10, Exceptional, (179)
"Beautiful location and property. The house is rustic and had trouble getting the heat to work. "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

Elevated Potomac River Retreat - King Suite - Riverfront - Large Screened Porch

10.0 out of 10, Exceptional, (5)
Elevated Potomac River Retreat - King Suite - Riverfront - Large Screened Porch

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

9.8 out of 10, Exceptional, (201)
"We had a great stay. The hosts were responsive. The cabin was beautiful with great views and a perfect getaway. Definitely would stay again."
Charming mountaintop cabin with hot tub, pool table, and breathtaking views

Cozy Lakeside Homestead

10.0 out of 10, Exceptional, (192)
"My wife and I loved our stay at this location. Was a perfect weekend getaway. We really enjoyed what the house had to offer, especially the hot tub, sauna, and fireplace. Made the cold rainy weather we had cozy and enjoyable as we huddled up inside. "
Cozy Lakeside Homestead

Happy Harbor | Mtn + Riverside w/ Game Room + Water Hole!

8.8 out of 10, Excellent, (23)
"Our large family loved coming together at this beautiful home! We enjoyed sitting around the large kitchen and beautiful living room while the teens and kids enjoyed the game room and the basketball area. We also loved having a large property to explore"
Happy Harbor | Mtn + Riverside w/ Game Room + Water Hole!

Newly renovated Farm cottage with Mountain views

9.8 out of 10, Exceptional, (29)
"The cottage was very charming and outfitted for maximum relaxation. We would definitely stay there again."
The price is AED 588
AED 1,199 total
includes taxes & fees
7 Jun - 8 Jun
Newly renovated Farm cottage with Mountain views

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (51)
"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "
The price is AED 494
AED 1,117 total
includes taxes & fees
9 Jun - 10 Jun
Cottage on King | Charming Historic Leesburg Home

King•Grill•Deck•Pets•Full Kitchen•Fire pit•SmartTV•WIFI

10.0 out of 10, Exceptional, (11)
"Accurate to the listing, good communications with owner"
The price is AED 760
AED 1,704 total
includes taxes & fees
6 Jun - 7 Jun
King•Grill•Deck•Pets•Full Kitchen•Fire pit•SmartTV•WIFI

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

10.0 out of 10, Exceptional, (372)
"This is a beautiful place to stay. The house is amazing and is sticked with almost everything'you need. The views are amazing. Will be returning "
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

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

9.8 out of 10, Exceptional, (222)
"Highly recommend staying here. We even had a little snow! Family friendly and cozy. "
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, (103)
"We had a wonderful stay at the Riverside cabin. With a beautiful view, perfect deck for reading, and a quiet house to get away in. So close to town and activities provided for a wonderful getaway. "
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Peaceful cottage in farmland - close to Luray, Shenandoah River & National Park

2.0 star property
10.0 out of 10, Exceptional, (7)
"After a week of road-tripping, this was a lovely final stay before gunning it back up north on I-81. Tidy and cute, with splendid backyard views of the valley and mountains. "
The price is AED 380
AED 832 total
includes taxes & fees
9 Jun - 10 Jun
Peaceful cottage in farmland - close to Luray, Shenandoah River & National Park

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

9.8 out of 10, Exceptional, (182)
"The location was exactly what we needed and wanted. If you want to totally relax, get semi off the grid, this is your place. Take a hike and take it all in. Thank you to our hosts for making such a great property available."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

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

9.8 out of 10, Exceptional, (96)
"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!"
The price is AED 2,163
AED 4,006 total
includes taxes & fees
3 Jul - 4 Jul
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Cozy 3 bedroom cabin with pretty views and a short drive to Luray Caverns

10.0 out of 10, Exceptional, (35)
"We had a great visit to the cabin, so easy and clean and great to bring our dogs on the family trip"
Cozy 3 bedroom cabin with pretty views and a short drive to Luray Caverns

Historic Hideaway

10.0 out of 10, Exceptional, (18)
"Spent the weekend here, perfect stay in a quiet area - 5 minute ride to shops, restaurants, and bars in downtown Leesburg. Everything was clean, well maintained. Would absolutely stay here again!"
The price is AED 446
AED 1,054 total
includes taxes & fees
9 Jun - 10 Jun
Historic Hideaway

Charming 2-bedroom house with WiFi, AC, Gorgeous Views in serene Middletown

2.0 star property
9.4 out of 10, Exceptional, (8)
"Absolutely loved this place. There was lots to do and the hosts were great communicators. They replied immediately to our texts and gave lots of information about the local area. The house was comfortable and in a great location with restaurants and beautiful walks nearby. "
Charming 2-bedroom house with WiFi, AC, Gorgeous Views in serene Middletown

Breathtaking View with an Indoor Pool

9.8 out of 10, Exceptional, (252)
"We have been coming for six years now and I expect we will come for 20 more. Love this house."
Breathtaking View with an Indoor Pool
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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