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Check prices for these dates

Next weekend
25 Rab. II - 27 Rab. II
In two weeks
2 Jum. I - 4 Jum. I
In one month
16 Jum. I - 18 Jum. I
In two months
13 Jum. II - 15 Jum. II

Compare 658 Vacation Homes in Winchester with updated reviews, rates, and availability.

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

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

9.8 out of 10, Exceptional, (199)
"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
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Smart TV, fireplace, books

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

10.0 out of 10, Exceptional, (44)
"Great property, so much space! And probably cleaner than any place I've stayed. Harpers Ferry is divi a cute little town and we enjoyed"
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Terrace/patio

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

9.8 out of 10, Exceptional, (97)
"This was a perfect clean comfortable place to stay while exploring the Harper's Ferry area. Hosts Scott and Margie are friendly and welcoming"
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)
"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
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

10.0 out of 10, Exceptional, (31)
"We were there over the Christmas holidays, The farmhouse was very nicely decorated for Christmas, we were very happy with the accommodations and would definitely stay there again"
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
Lovely home, wonderful location.
Fridge, microwave, oven, stovetop

Lovely home, wonderful location.

10.0 out of 10, Exceptional, (63)
"The house is very conveniently located to Luray cavern and Shenandoah national park where my family visited during our mini vacation!"
The price is SAR 488
SAR 909 total
includes taxes & fees
27 Apr - 28 Apr
Lovely home, wonderful location.
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Property grounds

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

10.0 out of 10, Exceptional, (115)
"Great communication with host. Cosy house, well equipped kitchen in a great location."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Secluded River Cabin Getaway (Masten Cabin)
Fridge, microwave, oven, stovetop

Secluded River Cabin Getaway (Masten Cabin)

9.8 out of 10, Exceptional, (146)
"Nice little cabin in the woods. Close to town if you need anything. Kids had a wonderful time. We would go again!"
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, (32)
"Overall was beautiful. Very easy to communicate with the owner. The view was breathtaking. I’d definitely recommend this to my other families and friends. Thanks again for making our stay so pleasant. "
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)
"Wonderful house and grounds for a family wedding."
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
Property grounds

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

9.8 out of 10, Exceptional, (218)
"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
Waterfront, Luxury Panoramic View, Fast Wi-Fi, Private River Access Steps Away!
Property grounds

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

10.0 out of 10, Exceptional, (44)
"We have rented Shiloh Lodge several times for fishing and hunting. The guys love this lodge. Convenient to the river and hunting across the road."
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, (94)
"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
Exterior

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

9.8 out of 10, Exceptional, (178)
"Beautiful location if you like alone time in the mountains."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Beautiful Log Chalet/Cabin with Hot Tub
Fridge, microwave, oven, stovetop

Beautiful Log Chalet/Cabin with Hot Tub

10.0 out of 10, Exceptional, (65)
"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, (44)
"Lots of space for everyone, excellent pool and hot tub"
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, (24)
"Had a good time staying at this house. Nice yard right on the river."
Waterfront property in Harpers Ferry - Private River Access
Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery
Terrace/patio

Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery

9.8 out of 10, Exceptional, (47)
"Great home for a family trip, very spacious for the family to spread out. "
Pets? YES! Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery
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, (311)
"very cute little place, would definitely stay again"
Star view cabin-Riverfront
Dreamtime - Modern A-frame Cabin w/ Hot tub
Smart TV, fireplace, books

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (37)
"We had a wonderful time staying here."
The price is SAR 1,084
SAR 1,374 total
includes taxes & fees
7 May - 8 May
Dreamtime - Modern A-frame Cabin w/ Hot tub
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Terrace/patio

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

9.8 out of 10, Exceptional, (97)
"This was a perfect clean comfortable place to stay while exploring the Harper's Ferry area. Hosts Scott and Margie are friendly and welcoming"
Riverside cottage, minutes from historic 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.