Winchester Holiday Rentals

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Check prices for these dates

Tonight
19 Oct - 20 Oct
Tomorrow
20 Oct - 21 Oct
Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov

Holiday Rentals in Winchester

Exterior
Cozy English Basement Apt quiet but close to downtown
Cozy English Basement Apt quiet but close to downtown
9.6 out of 10, Exceptional, (7)
"Downtown Winchester is charming, and the property was an easy walk from downtown (though in a safe suburban neighborhood). The property itself was just as advertised. I was able to cook meals there; the bed was comfortable; it was much nicer and more varied than a hotel room."
United States
Sherwood W.
The price is HK$777
HK$1,364 total
includes taxes & fees
20 Oct - 21 Oct
Cozy English Basement Apt quiet but close to downtown
Terrace/patio
Cute cabin retreat near Shenandoah National Park and pet friendly!
Cute cabin retreat near Shenandoah National Park and pet friendly!
9.4 out of 10, Exceptional, (12)
"Very relaxing end to out Appalachian Trail hike. The hot tub was so relaxing. It was the perfect way to end a strenuous day."
United States
Jean L.
The price is HK$1,282
HK$3,051 total
includes taxes & fees
6 Nov - 7 Nov
Cute cabin retreat near Shenandoah National Park and pet friendly!
Interior
Rosamond nice downtown studio apt
Rosamond nice downtown studio apt
8.0 out of 10, Very good, (2)
"Small but appropriately priced."
United States
John M.
The price is HK$855
HK$1,496 total
includes taxes & fees
13 Nov - 14 Nov
Rosamond nice downtown studio apt
Exterior
Wilderness Ridge | Private Cabin w/ Mountain Views
Wilderness Ridge | Private Cabin w/ Mountain Views
9.6 out of 10, Exceptional, (4)
"great get away for a family retreat!!!"
United States
Rex P.
The price is HK$1,554
HK$4,104 total
includes taxes & fees
2 Nov - 3 Nov
Wilderness Ridge | Private Cabin w/ Mountain Views
Exterior
Whitetail Cabin | Couple`s Retreat w/ Hot Tub
Whitetail Cabin | Couple`s Retreat w/ Hot Tub
10.0 out of 10, Exceptional, (21)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
The price is HK$1,080
HK$2,836 total
includes taxes & fees
17 Nov - 18 Nov
Whitetail Cabin | Couple`s Retreat w/ Hot Tub
Interior
Pretty Little Apt by the Train II
Pretty Little Apt by the Train II
2.0 star property
10.0 out of 10, Exceptional, (4)
"Great time. Love this city"
United States
Barbara B.
The price is HK$1,010
HK$1,672 total
includes taxes & fees
20 Oct - 21 Oct
Pretty Little Apt by the Train II
Property grounds
Private apartment on a beautiful private farm!
Private apartment on a beautiful private farm!
10.0 out of 10, Exceptional, (5)
"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$1,049
HK$2,099 total
includes taxes & fees
20 Oct - 21 Oct
Private apartment on a beautiful private farm!
Fridge, microwave, oven, stovetop
Mountain View Bungalow in Front Royal
Mountain View Bungalow in Front Royal
10.0 out of 10, Exceptional, (4)
"Property was just what we were looking for "
United States
Tim C.
The price is HK$1,049
HK$1,686 total
includes taxes & fees
26 Oct - 27 Oct
Mountain View Bungalow in Front Royal
Property grounds
Apple Mountain Retreat
Apple Mountain Retreat
10.0 out of 10, Exceptional, (19)
"Very nice place to stay within convenient distance to Front Royal and Shenandoah Natl Park. "
United States
Anonymous traveller
The price is HK$1,049
HK$1,800 total
includes taxes & fees
20 Oct - 21 Oct
Apple Mountain Retreat
Terrace/patio
The Cozy Bear Cabin | Hot Tub, Fenced Yard, Games
The Cozy Bear Cabin | Hot Tub, Fenced Yard, Games
10.0 out of 10, Exceptional, (3)
"We had a wonderful time staying there during our time at upperville. The quiet nights in the hot tub were just what we needed! Matthew was a wonderful host and so helpful ! We hope to come back again "
United States
grace g.
The price is HK$1,165
HK$3,290 total
includes taxes & fees
5 Nov - 6 Nov
The Cozy Bear Cabin | Hot Tub, Fenced Yard, Games
Exterior detail
The Blue Door steps from Handley Library
The Blue Door steps from Handley Library
2.0 star property
5.4 out of 10, (3)
"Perfect. Met all expectations. Small but Great."
United States
derric3k
The price is HK$893
HK$1,496 total
includes taxes & fees
5 Nov - 6 Nov
The Blue Door steps from Handley Library
Terrace/patio
Cabin Retreat in Virginia Wine Country – Hot Tub, Theater Room & Pet-Friendly
Cabin Retreat in Virginia Wine Country – Hot Tub, Theater Room & Pet-Friendly
9.8 out of 10, Exceptional, (10)
"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$1,453
HK$3,359 total
includes taxes & fees
4 Nov - 5 Nov
Cabin Retreat in Virginia Wine Country – Hot Tub, Theater Room & Pet-Friendly
Interior
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.
10.0 out of 10, Exceptional, (1)
"Jessica was a wonderful host. Outdoor table was lovely with a great view of a garden with cows as next door neighbors "
United States
Susan B.
The price is HK$1,049
HK$2,099 total
includes taxes & fees
3 Nov - 4 Nov
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Exterior
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
10.0 out of 10, Exceptional, (5)
"The house was perfect! It was clean, updated, and was in a great location near multiple wineries and hiking spots. The bed was comfortable, we liked the layout, and enjoyed the hot tub. We would definitely book this place again. The communication was great as well. "
United States
Melissa S.
The price is HK$1,204
HK$3,145 total
includes taxes & fees
5 Nov - 6 Nov
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
2 bedrooms, travel cot, WiFi, bed sheets
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
8.0 out of 10, Very good, (1)
"The listing indicated pets were welcome and we were able to bring our 13 year old dog, who loves traveling with my husband and I. There was some initial confusion after we booked the Schoolhouse, saying pets are prohibited. Through contact with the host, it was cleared up pretty quickly. All in all, the place was comfortable and we had what we needed to cook a couple of meals. I loved the area and enjoyed walking our dog on the state-maintained back roads. We would have liked to take advantage...
United States
Kathy S.
The price is HK$878
HK$2,721 total
includes taxes & fees
11 Nov - 12 Nov
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Terrace/patio
Luxury Riverfront Home Getaway with Hot Tub
Luxury Riverfront Home Getaway with Hot Tub
2.0 star property
The price is HK$1,546
HK$3,584 total
includes taxes & fees
4 Nov - 5 Nov
Luxury Riverfront Home Getaway with Hot Tub
Fridge, microwave, oven, stovetop
Yellow Submarine trendy basement apt and courtyard
Yellow Submarine trendy basement apt and courtyard
9.0 out of 10, Wonderful, (2)
"Very clean and comfortable. Really cool furniture pieces. Nice kitchen, dining room, living room. Will stay here again when in the area. "
United States
Eric N.
The price is HK$1,134
HK$1,998 total
includes taxes & fees
20 Oct - 21 Oct
Yellow Submarine trendy basement apt and courtyard
Outdoor dining
Newly renovated Farm cottage with Mountain views
Newly renovated Farm cottage with Mountain views
10.0 out of 10, Exceptional, (37)
"Very clean cottage with well-stocked kitchen with a great outdoors area for grilling and hanging out. Quiet relaxing location way up off the road. The hosts were unobtrusive but available. We have already recommended this cottage to our immediate family for future stays. "
United States
Becky C.
The price is HK$1,243
HK$2,519 total
includes taxes & fees
20 Oct - 21 Oct
Newly renovated Farm cottage with Mountain views
TV, fireplace, offices
Skyland Hideaway | Mountain Cabin w/ Hot Tub
Skyland Hideaway | Mountain Cabin w/ Hot Tub
10.0 out of 10, Exceptional, (14)
"We just stayed at SkyLand The house was clean, comfortable and welcoming. Matt is a great host Very responsive. The hot tub needed more water...no big deal. The beds were comfy and the coffee much appreciated upon arrival. Definitely wanna stay again."
United States
Virginia
The price is HK$1,398
HK$3,290 total
includes taxes & fees
2 Nov - 3 Nov
Skyland Hideaway | Mountain Cabin w/ Hot Tub
Property grounds
The Vue - Mountain top hot tub overlooking the Shenandoah River
The Vue - Mountain top hot tub overlooking the Shenandoah River
2.0 star property
9.8 out of 10, Exceptional, (7)
"Love the view and beautiful appointed decor throughout the home…"
United States
Lynn M.
The price is HK$1,527
HK$3,304 total
includes taxes & fees
6 Nov - 7 Nov
The Vue - Mountain top hot tub overlooking the Shenandoah River
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

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"Room was exceptionally clean. Quiet. Comfortable beds. Lots of parking. Staff very friendly helpful. Liked this hotel very much. Very reasonable dog fed "
Linda 1-night trip
Posted 3 days ago
Comfort Inn & Suites 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
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • 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?

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly: This holiday home rental outside of Winchester is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Winchester?

Choose from 17 Expedia holiday rentals in Winchester for a memorable holiday.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Nalls Farm Market 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.