Winchester Vacation Rentals

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Vacation Rentals in Winchester

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

10.0 out of 10, Exceptional, (98)
"Clean and nice place to stay to visit Shenandoah "
The price is ¥25,094
¥60,420 total
includes taxes & fees
Sep 29 - Sep 30
Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

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

9.8 out of 10, Exceptional, (283)
"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 ¥13,285
¥45,154 total
includes taxes & fees
Sep 29 - Sep 30
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Road Haven 1830

3.0 star property
9.6 out of 10, Exceptional, (36)
"Great place to stay! It’s clean cozy and quiet! I would definitely stay again in the future!"
The price is ¥19,042
¥21,383 total
includes taxes & fees
Sep 29 - Sep 30
Road Haven 1830

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (46)
"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 ¥28,932
¥35,846 total
includes taxes & fees
Oct 8 - Oct 9
Dreamtime - Modern A-frame Cabin w/ Hot tub

Canal Cabins

3.0 star property
9.6 out of 10, Exceptional, (9)
"Perfect for an over night Clean quiet simple. Ac needs repair"
The price is ¥18,266
¥20,640 total
includes taxes & fees
Sep 27 - Sep 28
Canal Cabins

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

10.0 out of 10, Exceptional, (47)
"Couldn't ask for a nicer place to stay peaceful, quiet with a great view. Wildlife is abundant and beautiful everything that you could need or want to relax Bill and Patty were excellent hosts looking forward to visiting again"
Private, light filled retreat space... with your own pickleball court!

Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill

9.6 out of 10, Exceptional, (11)
"Hot tub was nice relaxing cozy cabin"
The price is ¥11,063
¥28,756 total
includes taxes & fees
Sep 29 - Sep 30
Rustic Tabor Woods Cabin near Cacapon State Park w/Patio, Grill

Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

9.6 out of 10, Exceptional, (62)
"We had a great stay! The place was very clean, the back deck was such a great added bonus.. had a good selection of movies and games. 4 wheel drive is advisable. Very comfy!!"
The price is ¥20,938
¥48,591 total
includes taxes & fees
Oct 1 - Oct 2
Dog Friendly Cabin near River on Nearly 5 acres w/Strong WiFi + Robust Amenities

Falling Leaf Cabin - Rustic Charm With Modern Decor!

9.8 out of 10, Exceptional, (297)
"Well kept cabin in a secluded part of Shenandoah. Would book again!"
Falling Leaf Cabin - Rustic Charm With Modern Decor!

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (330)
"Great location, great views, "
Star view cabin-Riverfront

Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks

10.0 out of 10, Exceptional, (11)
"It was an amazing place, will recommend to friends and hopefully will be back."
The price is ¥22,083
¥36,666 total
includes taxes & fees
Oct 1 - Oct 2
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks

Endless Skies & Spectacular Views!!!

10.0 out of 10, Exceptional, (76)
"Gorgeous property, very peaceful, highly recommended!"
Endless Skies & Spectacular Views!!!

Modern Glass Retreat in Fort Valley with WiFi, AC, EV charger

10.0 out of 10, Exceptional, (6)
"This was a perfect weekend get away! Super clean. The host provided all the necessities that you might need like shampoo, soap, tissues, etc. The host was very prompt with responding to questions. Would definitely recommend! "
The price is ¥44,504
¥64,394 total
includes taxes & fees
Sep 29 - Sep 30
Modern Glass Retreat in Fort Valley with WiFi, AC, EV charger

The Oculus - Huge Cabin with a Hot Tub!

9.6 out of 10, Exceptional, (24)
"This was a great place for our vacation."
The price is ¥14,761
¥64,243 total
includes taxes & fees
Oct 9 - Oct 10
The Oculus - Huge Cabin with a Hot Tub!

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (61)
"We truly loved this location and definitely will be back!"
The price is ¥5,982
¥15,622 total
includes taxes & fees
Oct 5 - Oct 6
❤️ Secluded 1940s Romantic Tiny House on the River

1959 TOPLEY Retreat offers Serenity/Tranquility + Pets - Fenced Area/ FREE WIFI

10.0 out of 10, Exceptional, (8)
"This is a lovely home and super clean. My partner and I stayed here for a long weekend to go hiking around Shenandoah. Luray was also a nice little town."
The price is ¥25,832
¥42,719 total
includes taxes & fees
Sep 25 - Sep 26
1959 TOPLEY Retreat offers Serenity/Tranquility + Pets - Fenced Area/ FREE WIFI

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

9.8 out of 10, Exceptional, (123)
"The property was awesome. Very secluded, very clean, fully stocked. Check in is a little late and check out a little early, but would definitely stay again. The property was incredible with only little things like the electric fireplaces or the bubbles on the hottub not working. Plenty of space for a whole family, and plenty to do if you bring dogs. "
Private Log Cabin - Hot Tub, NEW SatelliteWi-Fi, Fireplace, Sm Pet Considered

Spectacular Views, Swimming Pool, Hot Tub, Real Log Fires, Mountain Getaway

9.4 out of 10, Exceptional, (144)
"Enjoyable. 4wd required"
Spectacular Views, Swimming Pool, Hot Tub, Real Log Fires, Mountain Getaway

Peaceful Waterfall House -- 2 bedroom hidden treasure

9.8 out of 10, Exceptional, (7)
"What a nice, history rich house to stay in. You can tell it has old bones but has been maintained and is full of character. Loved the relaxing setting with the river running around the house. Plenty to explore on the property down by the water and in the woods. Exactly what’s needed for a relaxing get away. Close to town as well for anything needed. Kirsten was a great host. "
The price is ¥29,625
¥46,609 total
includes taxes & fees
Sep 29 - Sep 30
Peaceful Waterfall House -- 2 bedroom hidden treasure

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

10.0 out of 10, Exceptional, (93)
"Very nice relaxing getaway, quite how do you spell quiet and serene location. "
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
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

Find out more about Winchester

Find out more about Winchester

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Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we offer vacation rentals in Winchester near Shenandoah Valley Discovery Museum, or you can go with a secluded option if you want a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theater scene while you're visiting.

What are some of the best vacation home rentals in Winchester?

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub: This vacation home near Winchester is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Winchester?

Choose from 16 Expedia vacation rentals in Winchester for a memorable vacation.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Nalls Farm Market are a couple of 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 vacation rental in Winchester like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Winchester. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for family trips.