Winchester, VA Vacation Homes from ￥34,787

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

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

In two months

In three months

In four months

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

Winchester

Carolyn F.

￥55,441 total

includes taxes & fees

Oct 6 - Oct 7

A wooden deck with white railings and a covered porch area.

2. Mountain View Bungalow in Front Royal

Front Royal

HEMANT S.

￥34,787 total

includes taxes & fees

Oct 6 - Oct 7

A garden with a wooden swing set and a circular seating area.

3. Newly renovated Farm cottage with Mountain views

Strasburg

Marsha N.

￥48,054 total

includes taxes & fees

Oct 6 - Oct 7

A single-story brick building with a front porch, a picnic table, and a barbecue grill.

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

Front Royal

￥65,639 total

includes taxes & fees

Oct 28 - Oct 29

A living room with a brick fireplace, a sofa, a television, and a window with a view of greenery.

5. Mountain home w/ hot tub & sunroom

Front Royal

Mollie S.

￥48,487 total

includes taxes & fees

Oct 27 - Oct 28

A blue sofa with a pink pillow, a white door, and a wall with motivational quotes and a 'blessed' sign.

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

Front Royal

￥55,517 total

includes taxes & fees

Nov 5 - Nov 6

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

Front Royal

A modern living room with a sectional sofa, a coffee table, and a TV displaying a Netflix interface.

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

Apple Mountain Lake

￥48,692 total

includes taxes & fees

Oct 6 - Oct 7

A living room with a fireplace, two sofas, a coffee table, and a large flat-screen TV above the fireplace.

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

Front Royal

￥71,420 total

includes taxes & fees

Oct 12 - Oct 13

A room with a large window, a round chair, a bar area with stools, and a dining table with chairs.

10. A-Frame Soak and Cedar near Skyline Drive and Wineries

Front Royal

A stone fireplace with a glass front, a wooden mantel shelf, and a cozy knitted throw on a chair.

11. Golfers' Paradise: 3 Courses Nearby + Pool Table

Front Royal

"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...

Crystal H.

￥90,093 total

includes taxes & fees

Oct 12 - Oct 13

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

Front Royal

Laura D.

A spacious loft bedroom with a large window, a cozy seating area, and a flat-screen TV.

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

Front Royal

Christine H.

￥106,729 total

includes taxes & fees

Oct 12 - Oct 13

A living room with a sofa, a television, a fireplace, and a ceiling fan.

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

Shenandoah Farms

"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...

Joshua J.

￥75,659 total

includes taxes & fees

Nov 3 - Nov 4