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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

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, (17 reviews)
"We enjoyed our stayed so much! This location is perfect. This property is so clean. "
United States
Nicole Z.
The price is £166
includes taxes & fees
7 Apr - 8 Apr
Mountain View Bungalow in Front Royal
Property grounds

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (39 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is £244
includes taxes & fees
5 Apr - 6 Apr
Newly renovated Farm cottage with Mountain views
TV, offices

Shenandoah mountain cottage w/hot tub & fire pit

Shenandoah mountain cottage w/hot tub & fire pit
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 £238
includes taxes & fees
14 Apr - 15 Apr
Shenandoah mountain cottage w/hot tub & fire pit
Terrace/patio

The Apple Mountain House

The Apple Mountain House
Front Royal
9.8 out of 10, Exceptional, (11 reviews)
"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"
United States
Katia R.
The price is £298
includes taxes & fees
14 Apr - 15 Apr
The Apple Mountain House
Property grounds

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
Linden
10.0 out of 10, Exceptional, (26 reviews)
"Very nice stay! A peaceful, quiet little place. Cozy beds! We enjoyed our time. "
United States
Katelyn E.
The price is £322
includes taxes & fees
28 Apr - 29 Apr
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
Exterior

Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.4 out of 10, Exceptional, (6 reviews)
"Nice house in a good central location. "
United States
Mitchell V.
The price is £258
includes taxes & fees
26 Apr - 27 Apr
Cameron Charmer pristine downtown apt with double master suites
Interior

The Rollason River Retreat - Four Bedroom Home with Game Room and Boat Access

The Rollason River Retreat - Four Bedroom Home with Game Room and Boat Access
Front Royal
The price is £316
includes taxes & fees
7 Apr - 8 Apr
The Rollason River Retreat - Four Bedroom Home with Game Room and Boat Access
TV, fireplace

25 min to SNP Forest Views, Deck and Game Lounge

25 min to SNP Forest Views, Deck and Game Lounge
Shenandoah Farms
The price is £430
includes taxes & fees
6 Apr - 7 Apr
25 min to SNP Forest Views, Deck and Game Lounge
Living area

Luxury Riverfront Home Getaway with Hot Tub

Luxury Riverfront Home Getaway with Hot Tub
Warren County
The price is £361
includes taxes & fees
13 Apr - 14 Apr
Luxury Riverfront Home Getaway with Hot Tub
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 £288
includes taxes & fees
21 Apr - 22 Apr
Bluemont home just minutes to wineries, breweries, hiking and more!
TV

Front royal majestic paradise

Front royal majestic paradise
Front Royal
The price is £1,173
includes taxes & fees
13 Apr - 14 Apr
Front royal majestic paradise
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, (39 reviews)
"Amazing stay in Luray, VA. House was very clean and up kept "
United States
Shedrick J.
The price is £241
includes taxes & fees
6 Apr - 7 Apr
Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly
Smart TV, Hulu, streaming services

Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4

Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4
Luray
9.8 out of 10, Exceptional, (68 reviews)
"This property was very clean and conveniently located to everything we wanted to do. We enjoyed our stay"
United States
Cindy H.
The price is £206
includes taxes & fees
16 Apr - 17 Apr
Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4
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 £273
includes taxes & fees
21 Apr - 22 Apr
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Smart TV, books, computer monitors

Leesburg Hideaway- King Bed + Private Backyard

Leesburg Hideaway- King Bed + Private Backyard
Leesburg
10.0 out of 10, Exceptional, (33 reviews)
"The host was great in communicating check in and check out instructions! We appreciated being able to park in the driveway and the fenced in back yard was also a nice amenity. Would definitely stay here again!"
United States
Katherine s.
The price is £231
includes taxes & fees
6 Apr - 7 Apr
Leesburg Hideaway- King Bed + Private Backyard
Exterior

Luray farmhouse on the river

Luray farmhouse on the river
Luray
9.4 out of 10, Exceptional, (45 reviews)
"Wonderful stay and everyone loved the house!Thank you!"
United States
roger c.
The price is £302
includes taxes & fees
6 Apr - 7 Apr
Luray farmhouse on the river
Outdoor dining

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets

Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Harpers Ferry
10.0 out of 10, Exceptional, (22 reviews)
"We had a great stay! The house was clean, nicely decorated and had every amenity we needed! "
United States
Julie H.
The price is £332
includes taxes & fees
6 Apr - 7 Apr
Firepit•BBQ•Hot Tub•King•Full Kitchen•SmartTV•Pets
Property grounds

Peaceful Retreat on Creekside

Peaceful Retreat on Creekside
Edinburg
9.2 out of 10, Wonderful, (17 reviews)
"Amazing location that was perfect for a weekend getaway! The creek was so peaceful and water views from the deck were amazing! "
United States
Richard D.
The price is £159
includes taxes & fees
6 Apr - 7 Apr
Peaceful Retreat on Creekside
Fridge, microwave, oven, stovetop

Cozy Wooded Cabin by National Park, EV Charger

Cozy Wooded Cabin by National Park, EV Charger
Star Tannery
10.0 out of 10, Exceptional, (6 reviews)
"This home was very secluded and had beautiful views. The interior was a perfect mix of historic and modern touches. Hosts were very responsive and we would stay here again!"
United States
Cyndi B.
The price is £275
includes taxes & fees
14 Apr - 15 Apr
Cozy Wooded Cabin by National Park, EV Charger
TV, fireplace, stereo, offices

Modern Cabin w Hot Tub & Indoor Pool/Gym Access!

Modern Cabin w Hot Tub & Indoor Pool/Gym Access!
The Woods
8.6 out of 10, Excellent, (10 reviews)
"Great location, everything was great and we would stay again!"
United States
Lauren P.
The price is £252
includes taxes & fees
5 Apr - 6 Apr
Modern Cabin w Hot Tub & Indoor Pool/Gym Access!
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Clean room, it’s our second visit and still just as clean as last visit."
King 1-night trip
Posted 8 hours ago
La Quinta Inn & Suites by Wyndham Winchester

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
278
Accommodation
632 Holiday Homes
Lowest Price
£159
Highest Price
£1,173