Winchester Holiday Rentals

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Holiday Rentals in Winchester

Canal Cabins

3.0 star property
10.0 out of 10, Exceptional, (3)
"All was expected. Nice Cabins"
The price is AU$193
includes taxes & fees
30 July - 31 July
Canal Cabins

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, "
The price is AU$557
includes taxes & fees
24 July - 25 July
Dreamtime - Modern A-frame Cabin w/ Hot tub

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

10.0 out of 10, Exceptional, (328)
"This cabin fulfilled all my needs. Simple, clean, and efficient. The location was secluded and quiet, just what I needed. Will definitely return!"
The price is AU$448
includes taxes & fees
2 July - 3 July
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

Summer at A Cozy Bear Cottage!

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!

Charming mountaintop cabin with hot tub, pool table, and breathtaking views

9.8 out of 10, Exceptional, (205)
"My wife and I had a great time exploring the surrounding area and had a wonderful time relaxing in the cabin. It was very clean!"
Charming mountaintop cabin with hot tub, pool table, and breathtaking views

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

9.8 out of 10, Exceptional, (291)
"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 price is AU$474
includes taxes & fees
8 July - 9 July
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA

Charming Cabin in the Woods with River Access

9.6 out of 10, Exceptional, (25)
"Wonderful little cabin situated perfectly in the area. Great access to the Potomac River and many little towns of interest nearby."
The price is AU$463
includes taxes & fees
20 July - 21 July
Charming Cabin in the Woods with River Access

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 AU$220
includes taxes & fees
2 July - 3 July
Family Farmhouse Inn

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (320)
"We had a wonderful time enjoying this peaceful setting. The house is just as described and everything worked well! "
Star view cabin-Riverfront

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

10.0 out of 10, Exceptional, (318)
"My wife & I needed a break from the daily grind & this place was exactly what the doctor ordered. Highly highly recommend this place to anyone. We hope to be able to return again sometime"
The price is AU$456
includes taxes & fees
9 July - 10 July
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

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 AU$402
includes taxes & fees
2 July - 3 July
Quaint Loft Cabin w/Hot Tub, FirePit, Deck & Grill

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

10.0 out of 10, Exceptional, (36)
"We enjoyed our stay here."
Private, light filled retreat space... with your own pickleball court!

Cabin near River, Firepit, Family-friendly, WiFi, Great Location, Veteran owned!

10.0 out of 10, Exceptional, (31)
"The house is great! We loved our stay. The place is even better than the listing. Know that you’re not particularly close to any restaurants or stores but that wasn’t an issue for us. You’re close to the park entrance. The lot is peaceful and an amazing place to unwind after a long day of hiking. "
Cabin near River, Firepit, Family-friendly, WiFi, Great Location, Veteran owned!

Outdoor Theatre | Hot Tub | Fire Pit | Dogs

10.0 out of 10, Exceptional, (43)
"It was a amazing stay"
The price is AU$505
includes taxes & fees
21 July - 22 July
Outdoor Theatre | Hot Tub | Fire Pit | Dogs

Lookout Cabin in the mountains, Amazing Views!

10.0 out of 10, Exceptional, (14)
"A small, quaint, mountain-top cabin close to Shenandoah National Park. The cabin was clean and cozy with all the amenities you need. Beautiful view from the living room and outdoor hot tub. "
The price is AU$524
includes taxes & fees
8 July - 9 July
Lookout Cabin in the mountains, Amazing Views!

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 by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

10.0 out of 10, Exceptional, (64)
"Very nice updated house 20 minutes from Shenandoah Park. "
The price is AU$473
includes taxes & fees
7 July - 8 July
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

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

9.8 out of 10, Exceptional, (56)
"The cabin is very nice with great location. We enjoyed our time there."
Riverfront🏕A-Frame/HOT TUB/Fire Pit! FAST Wifi

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

9.6 out of 10, Exceptional, (182)
"We had an extremely relaxing stay. The area is gorgeous…loved being close to the water. We brought our dog and it was great to let him run and play and just be a dog. Did have a few issues with a few appliances, but the host was super quick to bring a new remote and coffee pot. All in all we would stay again!"
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

Secluded River Cabin Getaway (Masten Cabin)

9.8 out of 10, Exceptional, (152)
"We had a wonderful stay! Cabin was clean and welcoming, beautiful views, and overall a charming, relaxing cabin in the woods!"
Secluded River Cabin Getaway (Masten Cabin)
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 20 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.