Winchester Holiday Rentals

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Check prices for these dates

Tonight
14 Jul - 15 Jul
Tomorrow
15 Jul - 16 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Holiday Rentals in Winchester

Canal Cabins
1 bedroom, pillow-top beds, free WiFi, bed sheets

Canal Cabins

3.0 star property
10.0 out of 10, Exceptional, (3)
"All was expected. Nice Cabins"
The price is HK$952
HK$1,076 total
includes taxes & fees
16 Jul - 17 Jul
Canal Cabins
Dreamtime - Modern A-frame Cabin w/ Hot tub
Outdoor dining

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (41)
"We stayed here for our anniversary and had a great time. Hosts were very responsive when we had a question about the hot tub, "
Dreamtime - Modern A-frame Cabin w/ Hot tub
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Property grounds

"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

9.8 out of 10, Exceptional, (292)
"We spent two night, and the place was wonderful. The views of the mountains are magical. The location is great, and close to so many attractions. Highly recommend a visit here."
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (321)
"We thoroughly enjoyed our stay here. From the moment you walk into the cabin, the views are spectacular and the surroundings are relaxing. We had a wonderful time and can’t wait to come back in the warmer weather to enjoy the outdoors more within a quick drive of lots of parks and scenic views Very clean and well appointed top-notch. "
Star view cabin-Riverfront
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Smart TV, books

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

10.0 out of 10, Exceptional, (66)
"Sweet l, well located property with everything you need for a stay! "
The price is HK$1,130
HK$2,426 total
includes taxes & fees
15 Jul - 16 Jul
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Secluded River Cabin Getaway (Masten Cabin)
Fridge, microwave, oven, stovetop

Secluded River Cabin Getaway (Masten Cabin)

9.8 out of 10, Exceptional, (156)
"It was clean. It had a beautiful drive to it and it was tucked up in the woods. It would be nice if there was curtains, but that is OK. You are surrounded by trees. Enjoyed our visit. Has a very cute town nearby. Wasn’t in the house very much was enjoying all the scenery."
Secluded River Cabin Getaway (Masten Cabin)
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Outdoor spa tub

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

10.0 out of 10, Exceptional, (331)
"The property was on a beautiful valley right next to the Shenandoah river. Everything was about as perfect as it could be. Would definitely recommend. "
The price is HK$1,374
HK$2,326 total
includes taxes & fees
20 Jul - 21 Jul
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Charming Cabin in the Woods with River Access
Exterior

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (27)
"Wonderful little cabin situated perfectly in the area. Great access to the Potomac River and many little towns of interest nearby."
The price is HK$1,280
HK$2,367 total
includes taxes & fees
20 Jul - 21 Jul
Charming Cabin in the Woods with River Access
Lookout Cabin in the mountains, Amazing Views!
Outdoor spa tub

Lookout Cabin in the mountains, Amazing Views!

10.0 out of 10, Exceptional, (14)
"Great spot - beautiful and laid back. Brian was very flexible which is greatly appreciated. "
The price is HK$1,517
HK$2,867 total
includes taxes & fees
20 Jul - 21 Jul
Lookout Cabin in the mountains, Amazing Views!
Summer at A Cozy Bear Cottage! New Furniture & lamps/lighting!
Exterior

Summer at A Cozy Bear Cottage! New Furniture & lamps/lighting!

10.0 out of 10, Exceptional, (61)
"Really nice place. Clean and tidy. The kitchen was well stocked with equipment and coffee. Close to some good hikes and Luray caverns. "
Summer at A Cozy Bear Cottage! New Furniture & lamps/lighting!
Falling Leaf Cabin - Rustic Charm With Modern Decor!
Exterior

Falling Leaf Cabin - Rustic Charm With Modern Decor!

9.8 out of 10, Exceptional, (288)
"Exceeded expectations."
Falling Leaf Cabin - Rustic Charm With Modern Decor!
Cottage on King | Charming Historic Leesburg Home
Terrace/patio

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (52)
"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "
The price is HK$1,410
HK$2,805 total
includes taxes & fees
22 Jul - 23 Jul
Cottage on King | Charming Historic Leesburg Home
Family Farmhouse Inn
Garden

Family Farmhouse Inn

3.0 star property
9.6 out of 10, Exceptional, (35)
"Great place to stay! It’s clean cozy and quiet! I would definitely stay again in the future!"
The price is HK$1,013
HK$1,137 total
includes taxes & fees
15 Jul - 16 Jul
Family Farmhouse Inn
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Outdoor dining

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (87)
"This beautiful cabin has everything you need for a wonderful stay. My husband and I stayed here for our 44th anniversary while visiting local wineries. It was a perfect location."
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Riverfront🏕A-Frame/HOT TUB/Fire Pit! FAST Wifi
Outdoor spa tub

Riverfront🏕A-Frame/HOT TUB/Fire Pit! FAST Wifi

9.8 out of 10, Exceptional, (58)
"The cabin is very nice with great location. We enjoyed our time there."
Riverfront🏕A-Frame/HOT TUB/Fire Pit! FAST Wifi
Quaint Loft Cabin w/Hot Tub, FirePit, Deck & Grill
Interior

Quaint Loft Cabin w/Hot Tub, FirePit, Deck & Grill

9.2 out of 10, Wonderful, (7)
"The cabin was peaceful and relaxing. Modern decor and nice outdoor amenities on the property. We enjoyed our stay."
The price is HK$1,156
HK$2,064 total
includes taxes & fees
15 Jul - 16 Jul
Quaint Loft Cabin w/Hot Tub, FirePit, Deck & Grill
Private Log Cabin - Hot Tub, NEW SatelliteWi-Fi, Fireplace, Sm Pet Considered
Exterior

Private Log Cabin - Hot Tub, NEW SatelliteWi-Fi, Fireplace, Sm Pet Considered

9.8 out of 10, Exceptional, (119)
"Peaceful, quiet, remote retreat. Enjoyed the hot tub and the beds were comfy. Walked around town and bought some treasures from the antique stores. Would recommend and will stay again."
Private Log Cabin - Hot Tub, NEW SatelliteWi-Fi, Fireplace, Sm Pet Considered
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Property grounds

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

9.6 out of 10, Exceptional, (184)
"Such a beautiful property. Very rustic charm inside. The screened in porch and rocking chairs made the weekend. Will return to this property in the future. "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Private, light filled retreat space... with your own pickleball court!
Smart TV, fireplace

Private, light filled retreat space... with your own pickleball court!

10.0 out of 10, Exceptional, (37)
"Beautiful vacation home situated on a picturesque landscape. Peaceful and quiet, it's everything you would hope for as a get-away. The owners are so very kind and helpful with anything you may need. Would definitely stay here again, and give my highest recommendation to other fellow travelers."
Private, light filled retreat space... with your own pickleball court!
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Exterior

Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

9.8 out of 10, Exceptional, (273)
"Very nice stay. We used the fire pit and hot tub and enjoyed both. Excellent location close to cacapon, we ended up hiking and doing the clay shooting. The cabin itself was very nice, cozy, and clean. "
The price is HK$1,095
HK$2,895 total
includes taxes & fees
17 Jul - 18 Jul
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
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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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 19 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 Museum of the Shenandoah Valley. Other places in town to visit include Patsy Cline Historic House and Jim Barnett Park.

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.