Winchester Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Winchester holiday rentals

Property grounds

Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (36 reviews)
"Great stay! The place was clean, comfortable, and exactly as described. Host was responsive and helpful. Would definitely stay again."
United States
Wafaa L.
The price is HK$1,489
HK$1,867 total
includes taxes & fees
23 Jun - 24 Jun
Blue Mountain Cabin, secluded, perfect for couples, near main road
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 HK$1,724
HK$3,688 total
includes taxes & fees
24 Jun - 25 Jun
Bluemont home just minutes to wineries, breweries, hiking and more!
Exterior

Blue Mountain House - Hot Tub, Grill, Fire Table

Blue Mountain House - Hot Tub, Grill, Fire Table
Linden
The price is HK$1,254
HK$3,536 total
includes taxes & fees
13 Jul - 14 Jul
Blue Mountain House - Hot Tub, Grill, Fire Table
Terrace/patio

Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
Stephens City
10.0 out of 10, Exceptional, (6 reviews)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
The price is HK$1,136
HK$1,439 total
includes taxes & fees
2 Jul - 3 Jul
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Fridge, microwave, oven, stovetop

Greek Spa • Private Acreage • Stonefire pizza oven

Greek Spa • Private Acreage • Stonefire pizza oven
Front Royal
The price is HK$886
HK$2,633 total
includes taxes & fees
24 Jun - 25 Jun
Greek Spa • Private Acreage • Stonefire pizza oven
TV

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Front Royal
9.6 out of 10, Exceptional, (17 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
The price is HK$1,164
HK$1,733 total
includes taxes & fees
30 Jun - 1 Jul
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Smart TV, books

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Winchester Historic District
8.8 out of 10, Excellent, (5 reviews)
"Large historic house at a great location "
United States
Bryan T.
The price is HK$1,082
HK$1,803 total
includes taxes & fees
23 Jun - 24 Jun
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
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 HK$1,129
HK$2,386 total
includes taxes & fees
23 Jun - 24 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 HK$1,058
HK$1,736 total
includes taxes & fees
25 Jun - 26 Jun
Mountain View Bungalow in Front Royal
TV, fireplace, table football, offices

Delicious Cabin • Wine Country Retreat w/ Hot Tub

Delicious Cabin • Wine Country Retreat w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (11 reviews)
"The cabin was impressive both inside and out. We loved the location and proximity to skyline drive. We would definitely stay here again as it made our trip so much more enjoyable. "
United States
Bill A.
The price is HK$1,379
HK$3,613 total
includes taxes & fees
28 Jun - 29 Jun
Delicious Cabin • Wine Country Retreat w/ Hot Tub
Dining

Comfy Getaway in Strasburg, VA!

Comfy Getaway in Strasburg, VA!
Strasburg
The price is HK$1,199
HK$3,009 total
includes taxes & fees
25 Jun - 26 Jun
Comfy Getaway in Strasburg, VA!
Outdoor spa tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (22 reviews)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
The price is HK$1,058
HK$3,017 total
includes taxes & fees
23 Jun - 24 Jun
The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Exterior

The Pond Cabin

The Pond Cabin
2.0 star property
Linden
The price is HK$1,873
HK$3,579 total
includes taxes & fees
30 Jun - 1 Jul
The Pond Cabin
Property grounds

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Bluemont
10.0 out of 10, Exceptional, (11 reviews)
"Our stay was great, and we had an excellent time in the area. Short drive to hiking spots and within walking distance to the local Bluemont Station restaurant. Highly recommend this stay in a quaint location!"
United States
Nicholas B.
The price is HK$1,107
HK$2,299 total
includes taxes & fees
23 Jun - 24 Jun
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Property grounds

The Haven at Turkey Run • Hot Tub, Fire Pit, Games

The Haven at Turkey Run • Hot Tub, Fire Pit, Games
Strasburg
10.0 out of 10, Exceptional, (14 reviews)
"Loved the creek and the hot tub!!! Cant say enough good things about this place"
United States
Maxx H.
The price is HK$1,379
HK$3,570 total
includes taxes & fees
15 Jul - 16 Jul
The Haven at Turkey Run • Hot Tub, Fire Pit, Games
Terrace/patio

Cozy English Basement Apt quiet but close to downtown

Cozy English Basement Apt quiet but close to downtown
Winchester
9.6 out of 10, Exceptional, (8 reviews)
"This property was the perfect stop for our overnight stay in Winchester. The perfect, quiet neighborhood very close to the walking mall. Just what we needed. "
United States
Anonymous traveller
The price is HK$784
HK$1,376 total
includes taxes & fees
2 Jul - 3 Jul
Cozy English Basement Apt quiet but close to downtown
Interior

Mountain cabin near national park & wineries

Mountain cabin near national park & wineries
Linden
10.0 out of 10, Exceptional, (31 reviews)
"It was a great place to stay and very clean."
United States
Chynna V.
The price is HK$1,481
HK$3,354 total
includes taxes & fees
23 Jun - 24 Jun
Mountain cabin near national park & wineries
Fridge, microwave, oven, stovetop

The Queen of Winchester Three Bedroom with Upper Level Deck

The Queen of Winchester Three Bedroom with Upper Level Deck
Winchester
7.8 out of 10, Good, (7 reviews)
"If you want to be in the town and have quick access to everything, this is the place for you."
United States
Chris C.
The price is HK$745
HK$1,635 total
includes taxes & fees
23 Jun - 24 Jun
The Queen of Winchester Three Bedroom with Upper Level Deck
Shower

Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
9.0 out of 10, Wonderful, (9 reviews)
"Stayed here with my 5 month old daughter, my mom and a friend and we had a blast. Kind folks, beautiful grounds and a super cute barn apartment! The fresh flowers in the kitchen were a lovely touch. "
United States
Haley M.
The price is HK$1,058
HK$2,117 total
includes taxes & fees
29 Jun - 30 Jun
Lunar Loft, with mountain views
Fridge, stovetop, coffee/tea maker, lobster pot

Buena Vista

Buena Vista
Shawneeland
The price is HK$823
HK$1,842 total
includes taxes & fees
7 Jul - 8 Jul
Buena Vista
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

Quality Inn Winchester

Quality Inn Winchester

8/10 Good
"It’s a bit dated, but clean"
Dianne 1-night trip
Posted 2 hours ago
Quality Inn Winchester

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
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  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Shenandoah Valley Discovery Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theatre scene while you're visiting.

What are some of the best holiday rentals that Winchester has to offer?

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.: This holiday home rental outside of Winchester offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Winchester?

Choose from 14 Expedia holiday rentals in Winchester for a memorable holiday.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Rocking S Ranch are a couple of the family-friendly sights, whereas cultural attractions include Bright Box Theater and Winchester Little Theater. Other places in town to visit include Patsy Cline Historic House and Museum of the Shenandoah Valley.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family getaway.