Winchester Holiday House Rentals from AU$301: Search Holiday Homes

Winchester Holiday Homes
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Our top choices for Winchester holiday homes

Shenandoah River Retreat: Pool Table and Fireplace

Front Royal

The price is AU$467

AU$467

includes taxes & fees

26 Jan - 27 Jan

Shenandoah River Retreat: Pool Table and Fireplace

Mountain View Bungalow in Front Royal

Front Royal

10.0 out of 10, Exceptional, (13 reviews)

10/10

Exceptional

(13 reviews)

"Property was just what we were looking for "

Tim C.

The price is AU$327

AU$327

includes taxes & fees

29 Jan - 30 Jan

Mountain View Bungalow in Front Royal

Lamontagne Farmhouse a Rural Pristine Setting

Bluemont

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"We loved our stay at this beautiful tranquil farmhouse. Our two Golden’s enjoyed the outdoor space. Hiking close by, a beautiful drive to visit Middleburg is a must. We highly recommend this charming getaway."

AnneMarie M.

The price is AU$354

AU$354

includes taxes & fees

26 Jan - 27 Jan

Lamontagne Farmhouse a Rural Pristine Setting

3 bedrooms, iron/ironing board, WiFi, bed sheets

Welcome to the Ladybug Retreat!

Boyce

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"This home is lovely and the host has thought of everything. We will definitely stay here again. "

Catherine A.

The price is AU$582

AU$582

includes taxes & fees

29 Jan - 30 Jan

Welcome to the Ladybug Retreat!

Newly renovated Farm cottage with Mountain views

Strasburg

10.0 out of 10, Exceptional, (38 reviews)

10/10

Exceptional

(38 reviews)

"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "

Shannon H.

The price is AU$470

AU$470

includes taxes & fees

22 Feb - 23 Feb

Newly renovated Farm cottage with Mountain views

Historic Bluemont Village Home

Bluemont

10.0 out of 10, Exceptional, (39 reviews)

10/10

Exceptional

(39 reviews)

"This was one of the best VRBO experiences I’ve had! Communication with the host was exceptional, and the home itself was gorgeous. It’s clear they have put a lot of thought into make this house a perfect getaway — it is beautifully decorated and has all the comforts of home. We will definitely stay here again!"

Mary S.

The price is AU$616

AU$616

includes taxes & fees

25 Jan - 26 Jan

Historic Bluemont Village Home

3 bedrooms, desk, iron/ironing board, travel cot

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

Linden

10.0 out of 10, Exceptional, (21 reviews)

10/10

Exceptional

(21 reviews)

"Very nice stay! A peaceful, quiet little place. Cozy beds! We enjoyed our time. "

Katelyn E.

The price is AU$470

AU$470

includes taxes & fees

26 Jan - 27 Jan

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

Big Sunny Family House

Front Royal

10.0 out of 10, Exceptional, (42 reviews)

10/10

Exceptional

(42 reviews)

"Wonderful house and town! Loved every minute of our trip! "

MaryAnn G.

The price is AU$589

AU$589

includes taxes & fees

28 Jan - 29 Jan

Big Sunny Family House

Bluemont home just minutes to wineries, breweries, hiking and more!

Bluemont

The price is AU$642

AU$642

includes taxes & fees

1 Feb - 2 Feb

Bluemont home just minutes to wineries, breweries, hiking and more!

Cameron Charmer pristine downtown apt with double master suites

Winchester

9.4 out of 10, Exceptional, (6 reviews)

9.4/10

Exceptional

(6 reviews)

"Nice house in a good central location. "

Mitchell V.

The price is AU$503

AU$503

includes taxes & fees

15 Feb - 16 Feb

Cameron Charmer pristine downtown apt with double master suites

Front royal majestic paradise

Front Royal

The price is AU$2,258

AU$2,258

includes taxes & fees

3 Feb - 4 Feb

Front royal majestic paradise

Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA

Linden

10.0 out of 10, Exceptional, (3 reviews)

10/10

Exceptional

(3 reviews)

"Megan was exceptional at communications, the property was perfect for our Family Thanksgiving. "

Lynne S.

The price is AU$814

AU$814

includes taxes & fees

26 Jan - 27 Jan

Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA

The Apple Mountain House

Front Royal

9.6 out of 10, Exceptional, (10 reviews)

9.6/10

Exceptional

(10 reviews)

"The stay was amazing! Breathtaking views, clean home, and wonderful amenities!!"

Katia R.

The price is AU$521

AU$521

includes taxes & fees

4 Feb - 5 Feb

The Apple Mountain House

3 bedrooms, iron/ironing board, free WiFi, bed sheets

On the river ~ hot tub ~ serene river views ~ fire pit

Strasburg

10.0 out of 10, Exceptional, (29 reviews)

10/10

Exceptional

(29 reviews)

"Our stay was wonderful. Everything was clean and inviting. The views were great!"

Ryann S.

The price is AU$807

AU$807

includes taxes & fees

1 Feb - 2 Feb

On the river ~ hot tub ~ serene river views ~ fire pit

New, Contemporary House in Historic Harpers Ferry

Harpers Ferry

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"The home was perfect for our visit.We were in and out all weekend but really appreciated the well stocked kitchen supplies, the comfortable beds and the hot water levels. We were able to relax in the spacious living room and spend some time on the little outdoor areas. We would stay again but if the group was much bigger there may be issues as there are only bathrooms on the first floor. "

Erin J.

The price is AU$543

AU$543

includes taxes & fees

25 Jan - 26 Jan

New, Contemporary House in Historic Harpers Ferry

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

Luray

10.0 out of 10, Exceptional, (65 reviews)

10/10

Exceptional

(65 reviews)

"This property was very clean and conveniently located to everything we wanted to do. We enjoyed our stay"

Cindy H.

The price is AU$301

AU$301

includes taxes & fees

2 Feb - 3 Feb

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

Peaceful cottage in farmland - close to Luray, Shenandoah River & National Park

Luray

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"Great stay- only one night for a friends wedding in Shenandoah. Nice place to stay, no issues! "

Jacquelin S.

The price is AU$403

AU$403

includes taxes & fees

1 Feb - 2 Feb

Peaceful cottage in farmland - close to Luray, Shenandoah River & National Park

The Blue Pearl by Zen Living

Luray

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"Such a cute place and just perfect!"

Anonymous traveller

The price is AU$407

AU$407

includes taxes & fees

1 Feb - 2 Feb

The Blue Pearl by Zen Living

Modern, family-friendly, nature packed getaway

Berkeley Springs

8.8 out of 10, Excellent, (21 reviews)

8.8/10

Excellent

(21 reviews)

"Great house! We loved the fire pit outside and the beautiful interior. Host was very responsive and helpful! Would def stay here again. "

Erika R.

The price is AU$396

AU$396

includes taxes & fees

25 Jan - 26 Jan

Modern, family-friendly, nature packed getaway

Tranquil Dome at Faraway Camp

Luray

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

The price is AU$464

AU$464

includes taxes & fees

28 Jan - 29 Jan

Tranquil Dome at Faraway Camp

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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