Search Vacation Homes in Winchester

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

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

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

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.
Property grounds

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

10.0 out of 10, Exceptional, (48)
"A spacious and very nice home located in a great location - walking distance to the best brewery and the best bakery in the area. Looking forward to visiting again soon! "
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, (100)
"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, (175)
"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)
"Fantastic weekend with my family...highly recommend 3 Penny Acres!"
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
Lovely home, wonderful location.
Exterior

Lovely home, wonderful location.

9.8 out of 10, Exceptional, (66)
"The house is very conveniently located to Luray cavern and Shenandoah national park where my family visited during our mini vacation!"
The price is AED 477
AED 1,004 total
includes taxes & fees
19 May - 20 May
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, (118)
"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)
Miscellaneous

Secluded River Cabin Getaway (Masten Cabin)

9.8 out of 10, Exceptional, (147)
"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, (33)
"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, (49)
"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
Outdoor dining

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

9.8 out of 10, Exceptional, (219)
"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
Cottage on King | Charming Historic Leesburg Home
Terrace/patio

Cottage on King | Charming Historic Leesburg Home

9.4 out of 10, Exceptional, (50)
"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "
The price is AED 432
AED 1,037 total
includes taxes & fees
11 May - 12 May
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)
"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

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

9.8 out of 10, Exceptional, (180)
"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
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, (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, (43)
"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

9.8 out of 10, Exceptional, (26)
"Had a good time staying at this house. Nice yard right on the river."
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchester

Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (313)
"very cute little place, would definitely stay again"
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, (37)
"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 1,333 total
includes taxes & fees
28 May - 29 May
Dreamtime - Modern A-frame Cabin w/ Hot tub
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people
Outdoor dining

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

9.2 out of 10, Wonderful, (13)
"Week with elderly family members and this home was a good spot to rest and relax. Upon arrival, house was neat and clean. Well stocked with cooking items. Nice layout. Good central locations for day trip options. Overall I would recommend this home. "
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people
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.