A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Search Vacation Homes in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winchester vacation homes

A two-story house with a front porch, a mailbox, and a number plate.

1. Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.6 out of 10, Exceptional, (9 reviews)
"The property was exceptional and very comfortable. We enjoyed the amenities. We would book it for future trips again."
United States
Carolyn F.
The price is AED 727
AED 1,294 total
includes taxes & fees
18 Oct - 19 Oct
Cameron Charmer pristine downtown apt with double master suites
A wooden deck with white railings and a covered porch area.

2. Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (45 reviews)
"Perfect place- would stay here again."
United States
HEMANT S.
The price is AED 496
AED 818 total
includes taxes & fees
18 Oct - 19 Oct
Mountain View Bungalow in Front Royal
A single-story brick building with a front porch, a picnic table, and a barbecue grill.

3. Shenandoah River House | 3BR - Private Dock - Pets

Shenandoah River House | 3BR - Private Dock - Pets
Front Royal
The price is AED 555
AED 1,561 total
includes taxes & fees
14 Oct - 15 Oct
Shenandoah River House | 3BR - Private Dock - Pets
A garden with a wooden swing set and a circular seating area.

4. Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (56 reviews)
"We enjoyed our stay here. The property was lovely and the house was nicely stocked and decorated. We will definitely stay again when in the area!"
United States
Marsha N.
The price is AED 588
AED 1,191 total
includes taxes & fees
18 Oct - 19 Oct
Newly renovated Farm cottage with Mountain views
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, and a view of the outdoors through a sliding door.

5. Cozy 3BR Retreat | Perfect for Families & Groups

Cozy 3BR Retreat | Perfect for Families & Groups
Apple Mountain Lake
The price is AED 444
AED 957 total
includes taxes & fees
14 Oct - 15 Oct
Cozy 3BR Retreat | Perfect for Families & Groups
A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

6. Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom
Front Royal
9.0 out of 10, Wonderful, (32 reviews)
"The cottage was amazing!! The hot tub was great and check in was super easy :) Internet and phone service were very good, and the cottage was stocked with all the kitchen utensils and linens we could have needed!"
United States
Mollie S.
The price is AED 591
AED 1,117 total
includes taxes & fees
27 Oct - 28 Oct
Mountain home w/ hot tub & sunroom
A two-story house with a porch, a small deck, and a gravel driveway.

7. Greek Spa - Frisbee Golf - Stone fire Pizza Oven

Greek Spa - Frisbee Golf - Stone fire Pizza Oven
Front Royal
The price is AED 320
AED 1,106 total
includes taxes & fees
14 Oct - 15 Oct
Greek Spa - Frisbee Golf - Stone fire Pizza Oven
Room

8. Trailside Retreat w/ Hot Tub, Sauna, Fireplace

Trailside Retreat w/ Hot Tub, Sauna, Fireplace
Front Royal
The price is AED 573
AED 1,860 total
includes taxes & fees
14 Oct - 15 Oct
Trailside Retreat w/ Hot Tub, Sauna, Fireplace
A spacious living room with a wooden coffee table, two leather sofas, a hanging light fixture, and a view of the adjacent kitchen.

9. Mountain Escape: Hottub + Fireplace + WiFi +PetsOK

Mountain Escape: Hottub + Fireplace + WiFi +PetsOK
Front Royal
The price is AED 514
AED 1,454 total
includes taxes & fees
2 Nov - 3 Nov
Mountain Escape: Hottub + Fireplace + WiFi +PetsOK
A stone fireplace with a glass front, a wooden mantel shelf, and a cozy knitted throw on a chair.

10. Pool Table, Fireplace & Deck near Shenandoah Park

Pool Table, Fireplace & Deck near Shenandoah Park
Front Royal
10.0 out of 10, Exceptional, (1 review)
"Home was clean and looked like it had recently been remodeled/updated. The host was very responsive and when the oven wasn't working properly, they went to Lowes and purchased a new one immediately! Made our short trip much easier not having to eat out or find a last minute option for our kids/babysitter on Friday evening. We were only in town from Thursday-Sunday, and it was perfect for the 5 of us. The pool table was a fun addition for the kids. The only minor complaint I have is that I wish I...
United States
Crystal H.
The price is AED 802
AED 2,080 total
includes taxes & fees
18 Oct - 19 Oct
Pool Table, Fireplace & Deck near Shenandoah Park
Ee757ed5 1522 44be bad8 24e0641215bd

11. Sunset Haven - 10 min from Skyline Drive. Hot Tub

Sunset Haven - 10 min from Skyline Drive. Hot Tub
Front Royal
9.6 out of 10, Exceptional, (8 reviews)
"Really enjoyed our stay. The house was lovely with amazing views. The bar and game room were fun. Lots of detail and thought were put into making this house feel like home. We will definitely be back!"
United States
Laura D.
The price is AED 1,074
AED 1,996 total
includes taxes & fees
14 Oct - 15 Oct
Sunset Haven - 10 min from Skyline Drive. Hot Tub
A spacious loft bedroom with a large window, a cozy seating area, and a flat-screen TV.

12. ⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!

⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
Front Royal
10.0 out of 10, Exceptional, (16 reviews)
"Taylor was great to work with! Nice property and wonderful view ."
United States
Christine H.
The price is AED 1,157
AED 2,467 total
includes taxes & fees
14 Oct - 15 Oct
⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
Local wineries, breweries, and small-town charm in Front Royal

13. Mountain Views w/Hot Tub, 95” TV & Trail Access

Mountain Views w/Hot Tub, 95” TV & Trail Access
Shenandoah Farms
10.0 out of 10, Exceptional, (1 review)
"We were looking for a comfortable home base to explore Front Royal and Skyline Plaza, and this was perfect! A modernized home with enough amenities that we were tempted every day to just stay “home!” The kids loved the reading nook and cozy sitting areas, and the fire pit and clean, working hot tub were big pluses as well. Kitchen was roomy, with great appliances and plenty of counter space. Beds were comfortable. Bathrooms were nice and modern. Lots of closet space, too. When we left, the kids...
United States
Joshua J.
The price is AED 1,024
AED 1,785 total
includes taxes & fees
14 Oct - 15 Oct
Mountain Views w/Hot Tub, 95” TV & Trail Access
A house with a well-lit entrance, a small garden, and a gravel driveway.

14. Custom Train-Themed Lodge on 7 Private Acres with Walking Trails

Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Martinsburg
9.8 out of 10, Exceptional, (24 reviews)
"Nice place to stay. Could use some privacy."
United States
Arnold A.
The price is AED 314
AED 954 total
includes taxes & fees
14 Oct - 15 Oct
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
A deck with outdoor seating and a lake view.

15. Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach

Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
Harpers Ferry
10.0 out of 10, Exceptional, (12 reviews)
"Had a wonderful stay here. Shaun was an excellent host with easy communication. Peaceful location with a lake! Convenient to Harper’s Ferry. "
United States
Liz P.
The price is AED 147
AED 907 total
includes taxes & fees
22 Oct - 23 Oct
Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach
A spacious living area with two grey sofas, a wooden floor, and a kitchen in the background.

16. Hidden Creekside retreat near 5 national parks, including Harpers Ferry

Hidden Creekside retreat near 5 national parks, including Harpers Ferry
Martinsburg
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful location and property."
United States
Helen F.
The price is AED 459
AED 1,129 total
includes taxes & fees
13 Nov - 14 Nov
Hidden Creekside retreat near 5 national parks, including Harpers Ferry
A bedroom with a bed, a chair, a nightstand, a ceiling fan, and a window with curtains.

17. Schilling House

Schilling House
3.0 star property
Bolivar
The price is AED 906
AED 1,153 total
includes taxes & fees
12 Nov - 13 Nov
Schilling House
An outdoor dining area with a table set for two, surrounded by chairs, and a grill on the right.

18. New Playground•Fenced Yard•Hot Tub•King Bed•Pets

New Playground•Fenced Yard•Hot Tub•King Bed•Pets
Harpers Ferry
10.0 out of 10, Exceptional, (37 reviews)
"Host was helpful and everything was wonderful."
United States
Karen
The price is AED 573
AED 1,467 total
includes taxes & fees
14 Oct - 15 Oct
New Playground•Fenced Yard•Hot Tub•King Bed•Pets
A hot tub with two glasses of red wine on a wooden tray.

19. GlampingDome + Ponds Cabin retreat near Capacon State Park in Berkeley Spring WV

GlampingDome + Ponds Cabin retreat near Capacon State Park in Berkeley Spring WV
Berkeley Springs
9.8 out of 10, Exceptional, (6 reviews)
"Wonderful quiet little getaway spot!! 10/10"
United States
Matthew C.
The price is AED 338
AED 1,194 total
includes taxes & fees
21 Oct - 22 Oct
GlampingDome + Ponds Cabin retreat near Capacon State Park in Berkeley Spring WV
An outdoor patio with a wooden deck, a hanging chair, a cushioned sofa, and various potted plants.

20. New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct

New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
Bolivar
9.8 out of 10, Exceptional, (49 reviews)
"Great location and incredibly well appointed!"
United States
Sarah M.
New AC. Luxury, Spa Bathroom, Movie Room, high-end design, fall colors Oct
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Lansdowne Resort and Spa

Lansdowne Resort and Spa

10/10 Excellent
"It’s a good place to attend weddings."
Umamaheshwar 1-night trip
Posted 3 hours ago
Lansdowne Resort and Spa

Explore a world of travel with Expedia