Holiday Homes in Winchester

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 June - 7 June
In four months
3 July - 5 July

Our top choices for Winchester holiday homes

Terrace/patio

Holiday Home in Front Royal

Mountain View Bungalow in Front Royal
10.0 out of 10, Exceptional, (15 reviews)
"Super cute, super clean and super comfortable!! Close and convenient to Shenandoah NP. Would definitely stay again!"
United States
Brian B.
The price is AU$310
includes taxes & fees
15 Mar - 16 Mar
Mountain View Bungalow in Front Royal
Property grounds

Holiday Home in Strasburg

Newly renovated Farm cottage with Mountain views
10.0 out of 10, Exceptional, (38 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is AU$458
includes taxes & fees
15 Mar - 16 Mar
Newly renovated Farm cottage with Mountain views
Smart TV, offices

Holiday Home in Middletown

Dog-Friendly Cottage w Playground, Grill & Games
9.6 out of 10, Exceptional, (16 reviews)
"Clean cute house, exactly as described. Close to Shenandoah national park and skyline drive. Hosts very communicative "
United States
Corrin D.
The price is AU$398
includes taxes & fees
23 Mar - 24 Mar
Dog-Friendly Cottage w Playground, Grill & Games
TV, offices

Holiday Home in Front Royal

Cozy mountain cottage w/hot tub & lake access
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$441
includes taxes & fees
17 Mar - 18 Mar
Cozy mountain cottage w/hot tub & lake access
Interior

Holiday Home in Winchester Historic District

Indigo Blue modern open vibe on tree lined street
10.0 out of 10, Exceptional, (13 reviews)
"Perfect for our needs for our daughter’s graduation!"
United States
Chris and Michelle P.
The price is AU$556
includes taxes & fees
15 Mar - 16 Mar
Indigo Blue modern open vibe on tree lined street
Exterior

Holiday Home in Winchester

Cameron Charmer pristine downtown apt with double master suites
9.4 out of 10, Exceptional, (6 reviews)
"Nice house in a good central location. "
United States
Mitchell V.
The price is AU$533
includes taxes & fees
14 Mar - 15 Mar
Cameron Charmer pristine downtown apt with double master suites
Terrace/patio

Holiday Home in Front Royal

The Apple Mountain House
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 AU$603
includes taxes & fees
22 Mar - 23 Mar
The Apple Mountain House
Terrace/patio

Holiday Home in Front Royal

Spacious home steps from Main St and Shenandoah NP with firepit & large backyard
9.8 out of 10, Exceptional, (18 reviews)
"Wonderful location. We were able to walk to restaurants and had a short drive to great hiking at Shenandoah National Park. "
United States
Mary F.
The price is AU$521
includes taxes & fees
15 Mar - 16 Mar
Spacious home steps from Main St and Shenandoah NP with firepit & large backyard
Property grounds

Holiday Home in Linden

🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
10.0 out of 10, Exceptional, (25 reviews)
"Very nice stay! A peaceful, quiet little place. Cozy beds! We enjoyed our time. "
United States
Katelyn E.
The price is AU$551
includes taxes & fees
17 Mar - 18 Mar
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
Exterior

Holiday Home in Stephens City

3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!
9.4 out of 10, Exceptional, (8 reviews)
"Had a great stay at this property for a girls weekend. Nearby to cute shops, a nice winery, grocery stores and restaurants. Nice amenities with games, entertainment systems, outdoor space, and in a great neighborhood too. Lots of space for families or friend reunions. Will rent again here when staying in the area. "
United States
Maureen W.
The price is AU$388
includes taxes & fees
16 Mar - 17 Mar
3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!
Exterior

Holiday Home in Front Royal

Big Sunny Family House
10.0 out of 10, Exceptional, (42 reviews)
"Wonderful house and town! Loved every minute of our trip! "
United States
MaryAnn G.
The price is AU$531
includes taxes & fees
23 Mar - 24 Mar
Big Sunny Family House
TV, fireplace

Holiday Home in Shenandoah Farms

25 min to SNP Forest Views, Deck and Game Lounge
The price is AU$741
includes taxes & fees
15 Mar - 16 Mar
25 min to SNP Forest Views, Deck and Game Lounge
Living area

Holiday Home in Warren County

Luxury Riverfront Home Getaway with Hot Tub
The price is AU$672
includes taxes & fees
16 Mar - 17 Mar
Luxury Riverfront Home Getaway with Hot Tub
Smart TV

Holiday Home in Boyce

Welcome to the Ladybug Retreat!
10.0 out of 10, Exceptional, (1 review)
"This home is lovely and the host has thought of everything. We will definitely stay here again. "
United States
Catherine A.
The price is AU$568
includes taxes & fees
18 Mar - 19 Mar
Welcome to the Ladybug Retreat!
Interior

Holiday Home in Front Royal

Litorum - a place to land, breathe, and reset.
The price is AU$562
includes taxes & fees
31 Mar - 1 Apr
Litorum - a place to land, breathe, and reset.
TV

Holiday Home in Front Royal

Front royal majestic paradise
The price is AU$2,151
includes taxes & fees
22 Mar - 23 Mar
Front royal majestic paradise
Exterior

Holiday Home in Warren County

Front Royal 5 bdrm 4 bth National park w/driveway
4.0 out of 10, (1 review)
"Very Disappointed, not a comfortable stay.1 No walkway to the front door. Have to walk through dirt/grass. We had to walk past spilled garbage with broken beer bottles to get to the front door, with a step that is in need of a repair.2 Living room only sits a few people w couches oriented one direction and TV a different direction. 3 Kitchen only sits 4 people.4 No garbage cans at all on the top floor which has 3 bedrooms & 2 bathrooms.5 No soap or towels in any of the bathrooms upon our...
United States
kim f.
The price is AU$702
includes taxes & fees
26 Mar - 27 Mar
Front Royal 5 bdrm 4 bth National park w/driveway
Outdoor dining

Holiday Home in Wardensville

Cozy Lakeside Homestead
10.0 out of 10, Exceptional, (206 reviews)
"My family and I had a great stay. The home was cozy, clean and relaxing. Great communication and the home had everything we needed for an awesome weekend. "
United States
Jeremy O.
The price is AU$378
includes taxes & fees
16 Mar - 17 Mar
Cozy Lakeside Homestead
Exterior

Holiday Home in Luray

Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly
9.8 out of 10, Exceptional, (38 reviews)
"Amazing stay in Luray, VA. House was very clean and up kept "
United States
Shedrick J.
The price is AU$477
includes taxes & fees
15 Mar - 16 Mar
Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly
Smart TV, Hulu, streaming services

Holiday Home in Luray

Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4
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 AU$338
includes taxes & fees
24 Mar - 25 Mar
Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4
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

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

10/10 Excellent
"Cute location "
Anne 2-night trip
Posted 4 hours ago
The George Washington Hotel, A Wyndham Grand Hotel

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
423
Accommodation
632 Holiday Homes
Lowest Price
AU$310
Highest Price
AU$2,151