Holiday Homes in Winchester

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
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

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 €269
includes taxes & fees
24 Jun - 25 Jun
Newly renovated Farm cottage with Mountain views
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 €196
includes taxes & fees
25 Jun - 26 Jun
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 €405
includes taxes & fees
24 Jun - 25 Jun
Bluemont home just minutes to wineries, breweries, hiking and more!
Fridge, microwave, oven, stovetop

Greek Spa • Private Acreage • Stonefire pizza oven

Greek Spa • Private Acreage • Stonefire pizza oven
Front Royal
The price is €266
includes taxes & fees
24 Jun - 25 Jun
Greek Spa • Private Acreage • Stonefire pizza oven
Dining

Comfy Getaway in Strasburg, VA!

Comfy Getaway in Strasburg, VA!
Strasburg
The price is €326
includes taxes & fees
24 Jun - 25 Jun
Comfy Getaway in Strasburg, VA!
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 €282
includes taxes & fees
28 Jun - 29 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, (9 reviews)
"Nice house in a good central location. "
United States
Mitchell V.
The price is €306
includes taxes & fees
24 Jun - 25 Jun
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 €354
includes taxes & fees
24 Jun - 25 Jun
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 €458
includes taxes & fees
14 Jul - 15 Jul
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 €652
includes taxes & fees
24 Jun - 25 Jun
⭐️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 €530
includes taxes & fees
21 Jul - 22 Jul
4BR Golf Retreat | 3 Courses | Pool Table
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, (93 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 €229
includes taxes & fees
24 Jun - 25 Jun
Historical home, walkable to many restaurants and shops.
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 €333
includes taxes & fees
25 Jun - 26 Jun
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 €237
includes taxes & fees
24 Jun - 25 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, (49 reviews)
"Amazing stay in Luray, VA. House was very clean and up kept "
United States
Shedrick J.
The price is €307
includes taxes & fees
24 Jun - 25 Jun
Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly
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 €287
includes taxes & fees
30 Jun - 1 Jul
Mountain Retreat w/2 Living Spaces, Hot Tub & Deck
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 €318
includes taxes & fees
8 Jul - 9 Jul
The Blue Jay | New House in the Woods w/ Hot Tub
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 €306
includes taxes & fees
24 Jun - 25 Jun
Mountain Summit Views Hot Tub-Fire Pit-BBQ, Pets
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 €288
includes taxes & fees
30 Jun - 1 Jul
Luray Escape . Hot Tub . 15 Min to Skyline Drive
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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Best set-up for accessible that we have seen."
Tim 1-night trip
Posted 1 hour ago
Comfort Inn & Suites Winchester

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
279
Accommodation
688 Holiday Homes
Lowest Price
€196
Highest Price
€652