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
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Winchester vacation homes

Property grounds

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (45 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is AED 529
AED 1,118 total
includes taxes & fees
22 Jun - 23 Jun
Newly renovated Farm cottage with Mountain views
Interior

Bluemont home just minutes to wineries, breweries, hiking and more!

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
The price is AED 459
AED 1,283 total
includes taxes & fees
23 Jun - 24 Jun
Bluemont home just minutes to wineries, breweries, hiking and more!
Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (27 reviews)
"We had a great stay! The house is cozy and just perfect for a private get away. The hosts were very communicative and wonderful, we will be back! "
United States
Virginia A.
The price is AED 496
AED 814 total
includes taxes & fees
25 Jun - 26 Jun
Mountain View Bungalow in Front Royal
TV, offices

Mountain home w/ hot tub & sunroom

Mountain home w/ hot tub & sunroom
Front Royal
9.0 out of 10, Wonderful, (31 reviews)
"The house itself was clean, the beds are comfortable, and it is in a nice, quiet, and private location. The property manager was very pleasant and responsed to any questions or concerns quickly. "
United States
Elissa S.
The price is AED 647
AED 1,182 total
includes taxes & fees
25 Jun - 26 Jun
Mountain home w/ hot tub & sunroom
Exterior

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, (8 reviews)
"Nice house in a good central location. "
United States
Mitchell V.
The price is AED 727
AED 1,298 total
includes taxes & fees
21 Jun - 22 Jun
Cameron Charmer pristine downtown apt with double master suites
Fridge, microwave, oven, stovetop

Greek Spa • Private Acreage • Stonefire pizza oven

Greek Spa • Private Acreage • Stonefire pizza oven
Front Royal
The price is AED 386
AED 1,201 total
includes taxes & fees
22 Jun - 23 Jun
Greek Spa • Private Acreage • Stonefire pizza oven
Dining

Comfy Getaway in Strasburg, VA!

Comfy Getaway in Strasburg, VA!
Strasburg
The price is AED 582
AED 1,424 total
includes taxes & fees
23 Jun - 24 Jun
Comfy Getaway in Strasburg, VA!
Living area

Luxury Riverfront Home Getaway with Hot Tub

Luxury Riverfront Home Getaway with Hot Tub
Warren County
The price is AED 992
AED 1,981 total
includes taxes & fees
14 Jul - 15 Jul
Luxury Riverfront Home Getaway with Hot Tub
Interior

4BR Golf Retreat • 3 Courses • Pool Table

4BR Golf Retreat • 3 Courses • Pool Table
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 1,003
AED 2,305 total
includes taxes & fees
16 Jul - 17 Jul
4BR Golf Retreat • 3 Courses • Pool Table
Smart TV, fireplace, video games, foosball

⭐️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, (12 reviews)
"Roomy, well stocked kitchen, and great view. Appreciated the chopsticks!"
United States
Brian T.
The price is AED 1,349
AED 2,707 total
includes taxes & fees
21 Jun - 22 Jun
⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres with HOT TUB!
Fridge, microwave, oven, stovetop

Historical home, walkable to many restaurants and shops.

Historical home, walkable to many restaurants and shops.
Luray
9.8 out of 10, Exceptional, (91 reviews)
"This is a very charming property and walkable to lots of cute shopping and the River Walk. We had a little hiccup at check in and it was taken care of so promptly!"
United States
Nicky T.
The price is AED 440
AED 960 total
includes taxes & fees
24 Jun - 25 Jun
Historical home, walkable to many restaurants and shops.
Property grounds

The Blue Jay | New House in the Woods w/ Hot Tub

The Blue Jay | New House in the Woods w/ Hot Tub
Harpers Ferry
10.0 out of 10, Exceptional, (3 reviews)
"Great place. Very well stocked house everything you need Great response from host. Very nice place. Road is a little rough as explained in listing "
United States
Brett D.
The price is AED 367
AED 1,353 total
includes taxes & fees
1 Jul - 2 Jul
The Blue Jay | New House in the Woods w/ Hot Tub
Smart TV, books, computer monitors

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (35 reviews)
"Adorable, comfy, private & well appointed. Well cleared of snow for our arrival after a difficult snow/ice storm. Comfortable mattress was a bonus. We enjoyed our stay! "
United States
Amy M.
The price is AED 678
AED 1,350 total
includes taxes & fees
22 Jun - 23 Jun
Leesburg Hideaway- King Bed + Private Backyard
Bathtub, hair dryer, towels, soap

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, (23 reviews)
"Host was super nice and location was pretty. "
United States
Kimberly B.
The price is AED 380
AED 1,028 total
includes taxes & fees
22 Jun - 23 Jun
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Terrace/patio

Huckleberry Hills | Hot Tub & Fire Pit & Dogs

Huckleberry Hills | Hot Tub & Fire Pit & Dogs
Harpers Ferry
9.8 out of 10, Exceptional, (11 reviews)
"We had a great stay "
United States
Lauren O.
The price is AED 419
AED 1,572 total
includes taxes & fees
24 Jun - 25 Jun
Huckleberry Hills | Hot Tub & Fire Pit & Dogs
Dining

Modern, family-friendly, nature packed getaway

Modern, family-friendly, nature packed getaway
Berkeley Springs
9.0 out of 10, Wonderful, (26 reviews)
The price is AED 459
AED 1,002 total
includes taxes & fees
22 Jun - 23 Jun
Modern, family-friendly, nature packed getaway
Exterior

Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly

Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly
Luray
9.8 out of 10, Exceptional, (48 reviews)
"Amazing stay in Luray, VA. House was very clean and up kept "
United States
Shedrick J.
The price is AED 496
AED 1,254 total
includes taxes & fees
23 Jun - 24 Jun
Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly
Interior

Rustic Barn Retreat w Hot Tub, Game Room & FirePit

Rustic Barn Retreat w Hot Tub, Game Room & FirePit
Wardensville
The price is AED 784
AED 1,507 total
includes taxes & fees
21 Jun - 22 Jun
Rustic Barn Retreat w Hot Tub, Game Room & FirePit
Outdoor spa tub

Mountain Summit Views Hot Tub-Fire Pit-BBQ, Pets

Mountain Summit Views Hot Tub-Fire Pit-BBQ, Pets
Page County
The price is AED 623
AED 1,350 total
includes taxes & fees
22 Jun - 23 Jun
Mountain Summit Views Hot Tub-Fire Pit-BBQ, Pets
Smart TV, fireplace

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Harpers Ferry
10.0 out of 10, Exceptional, (7 reviews)
"Welcoming host, great place!"
United States
Amanda M.
The price is AED 456
AED 1,325 total
includes taxes & fees
24 Jun - 25 Jun
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
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

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"I booked this room for one night, to break up a long drive, and since it’s summer, I specifically wanted a pool. This hotel is right off the interstate, and the pool is very large and well maintained. The rooms are nicer than you’d expect, and all the things you want to work, actually worked (tv, ice machines, etc.) The sunset from the pool area was spectacular, just as a bonus."
Jennifer 1-night trip
Posted 2 hours ago
Quality Inn Winchester

Explore a world of travel with Expedia