Holiday Homes in Winchester

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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

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, (16 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 €192
includes taxes & fees
22 Mar - 23 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 €281
includes taxes & fees
22 Mar - 23 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, (17 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 €250
includes taxes & fees
22 Mar - 23 Mar
Dog-Friendly Cottage w Playground, Grill & Games
TV, offices

Holiday Home in Front Royal

Shenandoah mountain cottage w/ hot tub & lake
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 €273
includes taxes & fees
19 Mar - 20 Mar
Shenandoah mountain cottage w/ hot tub & lake
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 €348
includes taxes & fees
14 Apr - 15 Apr
Indigo Blue modern open vibe on tree lined street
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 €336
includes taxes & fees
22 Mar - 23 Mar
The Apple Mountain House
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 €352
includes taxes & fees
24 Mar - 25 Mar
🔥 Hottub + 🐕 friendly + 🏔️ view + Skyline Dr + Wineries
TV, fireplace

Holiday Home in Shenandoah Farms

25 min to SNP Forest Views, Deck and Game Lounge
The price is €461
includes taxes & fees
23 Mar - 24 Mar
25 min to SNP Forest Views, Deck and Game Lounge
Interior

Holiday Home in Front Royal

Litorum - a place to land, breathe, and reset.
The price is €359
includes taxes & fees
27 Mar - 28 Mar
Litorum - a place to land, breathe, and reset.
Living area

Holiday Home in Warren County

Luxury Riverfront Home Getaway with Hot Tub
The price is €418
includes taxes & fees
22 Mar - 23 Mar
Luxury Riverfront Home Getaway with Hot Tub
TV

Holiday Home in Front Royal

Front royal majestic paradise
The price is €1,356
includes taxes & fees
1 Apr - 2 Apr
Front royal majestic paradise
Outdoor dining

Holiday Home in Wardensville

Cozy Lakeside Homestead
10.0 out of 10, Exceptional, (208 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 €232
includes taxes & fees
23 Mar - 24 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 €289
includes taxes & fees
19 Mar - 20 Mar
Spacious 3BR Townhome Near Luray Caverns & Shenandoah, Family & Pet-Friendly
Property grounds

Holiday Home in Harpers Ferry

Single Level, 3 Bedroom Home In Between Harper's Ferry & Casino.
7.6 out of 10, Good, (27 reviews)
"The inside was well done and clean. Even though the neighbors are close, they were quiet. My husband and I were able to relax in a comfortable setting."
United States
Melissa H.
The price is €257
includes taxes & fees
23 Mar - 24 Mar
Single Level, 3 Bedroom Home In Between Harper's Ferry & Casino.
Terrace/patio

Holiday Home in Rileyville

Sunset Mountain Cabin
9.8 out of 10, Exceptional, (37 reviews)
"Absolutely enjoyed our time here! So peaceful and beautiful! The host was amazing and very responsive! Loved the hot tub and how very open the space was. Definitely would come back!"
United States
Kim B.
The price is €344
includes taxes & fees
22 Mar - 23 Mar
Sunset Mountain Cabin
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 €209
includes taxes & fees
24 Mar - 25 Mar
Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4
Dining

Holiday Home in Berkeley Springs

Modern, family-friendly, nature packed getaway
9.0 out of 10, Wonderful, (24 reviews)
"Great house! We loved the fire pit outside and the beautiful interior. Host was very responsive and helpful! Would def stay here again. "
United States
Erika R.
The price is €233
includes taxes & fees
19 Mar - 20 Mar
Modern, family-friendly, nature packed getaway
2 bedrooms, travel cot, WiFi, bed sheets

Holiday Home in Harpers Ferry

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
10.0 out of 10, Exceptional, (16 reviews)
"Great spot"
China
Clara
The price is €270
includes taxes & fees
22 Mar - 23 Mar
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
House, 4 Bedrooms | Interior

Holiday Home in Wardensville

Heishman Historic Hillside Home 4 Bedroom Home
3.0 star property
The price is €306
includes taxes & fees
22 Mar - 23 Mar
Heishman Historic Hillside Home 4 Bedroom Home
Property grounds

Holiday Home in Edinburg

Peaceful Retreat on Creekside
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 €184
includes taxes & fees
19 Mar - 20 Mar
Peaceful Retreat on Creekside
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

Lansdowne Resort and Spa

Lansdowne Resort and Spa

8/10 Good
"Beautiful hotel -rooms were very spacious, pool was great, bar has nice selection and staff. We were there in March so outdoor pool etc was not open but it looked pretty with waterfalls etc.Spa was nice but very expensive. "
Gina 4-night trip
Posted 3 hours ago
Lansdowne Resort and Spa

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
436
Accommodation
632 Holiday Homes
Lowest Price
€184
Highest Price
€1,356