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Holiday Homes in Winchester

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Check prices for these dates

In two weeks
10 July - 12 July
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Winchester holiday homes

Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (29 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 AU$325
includes taxes & fees
1 July - 2 July
Mountain View Bungalow in Front Royal
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 AU$672
includes taxes & fees
28 July - 29 July
Bluemont home just minutes to wineries, breweries, hiking and more!
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 AU$439
includes taxes & fees
14 July - 15 July
Newly renovated Farm cottage with Mountain views
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 AU$447
includes taxes & fees
28 June - 29 June
Mountain home w/ hot tub & sunroom
Fridge, microwave, oven, stovetop

Greek Spa • Private Acreage • Stonefire pizza oven

Greek Spa • Private Acreage • Stonefire pizza oven
Front Royal
The price is AU$491
includes taxes & fees
29 June - 30 June
Greek Spa • Private Acreage • Stonefire pizza oven
Dining

Comfy Getaway in Strasburg, VA!

Comfy Getaway in Strasburg, VA!
Strasburg
The price is AU$471
includes taxes & fees
30 June - 1 July
Comfy Getaway in Strasburg, VA!
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, (9 reviews)
"Nice house in a good central location. "
United States
Mitchell V.
The price is AU$508
includes taxes & fees
28 June - 29 June
Cameron Charmer pristine downtown apt with double master suites
Fridge, microwave, oven, stovetop

Bend of Brothers’ | Riverfront Cottage Shenandoah

Bend of Brothers’ | Riverfront Cottage Shenandoah
Front Royal
The price is AU$575
includes taxes & fees
28 June - 29 June
Bend of Brothers’ | Riverfront Cottage Shenandoah
Living area

Luxury Riverfront Home Getaway with Hot Tub

Luxury Riverfront Home Getaway with Hot Tub
Warren County
The price is AU$768
includes taxes & fees
20 July - 21 July
Luxury Riverfront Home Getaway with Hot Tub
Smart TV, fireplace, video games, table football

⭐️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 AU$1,057
includes taxes & fees
6 July - 7 July
⭐️Lunar Lookout ⭐️ Geodesic Dome on 8 acres 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 AU$830
includes taxes & fees
21 July - 22 July
4BR Golf Retreat | 3 Courses | Pool Table
Outdoor dining

Luna A-Frame | King Suite, Fire Pit & Hot Tub

Luna A-Frame | King Suite, Fire Pit & Hot Tub
Berkeley Springs
10.0 out of 10, Exceptional, (1 review)
"The view was great and the sunrise was even better. Very clean with plenty of amenities. Not to far from town, but very quiet location."
United States
Michael
The price is AU$541
includes taxes & fees
28 June - 29 June
Luna A-Frame | King Suite, Fire Pit & Hot Tub
Dining

Modern, family-friendly, nature packed getaway

Modern, family-friendly, nature packed getaway
Berkeley Springs
9.0 out of 10, Wonderful, (26 reviews)
"House was very clean and well stocked! Very comfortable and within short distance of a lovely town Berkley Springs."
United States
Annie W.
The price is AU$395
includes taxes & fees
28 June - 29 June
Modern, family-friendly, nature packed getaway
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 AU$531
includes taxes & fees
28 June - 29 June
The Blue Jay | New House in the Woods w/ Hot Tub
Fridge, oven, stovetop, dishwasher

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck

Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
Harpers Ferry
The price is AU$474
includes taxes & fees
12 July - 13 July
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
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, (49 reviews)
"Amazing stay in Luray, VA. House was very clean and up kept "
United States
Shedrick J.
The price is AU$509
includes taxes & fees
30 June - 1 July
Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly
Property grounds

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline

4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
Harpers Ferry
9.6 out of 10, Exceptional, (5 reviews)
"House was beautiful and fully equipped for our stay. The host was very communicative and we really enjoyed our time here. If in the area again would definitely stay here. "
United States
Maeve K.
The price is AU$592
includes taxes & fees
29 June - 30 June
4-bedroom house close to Shenandoah River and VA wineries - WiFi, AC, trampoline
Outdoor spa tub

Luray Escape . Hot Tub . 15 Min to Skyline Drive

Luray Escape . Hot Tub . 15 Min to Skyline Drive
Luray
9.4 out of 10, Exceptional, (13 reviews)
"Such a cute place and just perfect!"
United States
Anonymous traveller
The price is AU$418
includes taxes & fees
30 June - 1 July
Luray Escape . Hot Tub . 15 Min to Skyline Drive
Exterior

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)
"Host was super nice and location was pretty. "
United States
Kimberly B.
The price is AU$413
includes taxes & fees
19 July - 20 July
Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
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 AU$443
includes taxes & fees
29 June - 30 June
Leesburg Hideaway- King Bed + Private Backyard
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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Top Winchester Hotel Reviews

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"The hotel was comfortable and clean."
Don 1-night trip
Posted 4 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
252
Accommodation
687 Holiday Homes
Lowest Price
AU$325
Highest Price
AU$1,057