Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Winchester

Property grounds
Hidden Gem in the woods with hot tub

Hidden Gem in the woods with hot tub

Berkeley Springs
9.6 out of 10, Exceptional, (86)
"Beautiful cabin. Updated photos are accurate but the space is even bigger in person. Hot tub and fire pit were great. House is clean and well equipped. Would stay again in a heartbeat. "
United States
Paul P.
Hidden Gem in the woods with hot tub
Smart TV, fireplace
Private, light filled retreat space... with your own pickleball court!

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

Berkeley Springs
10.0 out of 10, Exceptional, (59)
"We loved this place! The view was beautiful. Enjoyed the pickleball court. Would highly recommend it to anyone looking for a relaxing getaway!"
United States
Denise H.
Private, light filled retreat space... with your own pickleball court!
Exterior
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

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

Berkeley Springs
9.8 out of 10, Exceptional, (289)
"It was a great time, easy check in and out! Grill and hot tub were great, and there was an amazing view of the stars."
United States
Julian B.
The price is ￥13,865
￥47,127 total
includes taxes & fees
Nov 16 - Nov 17
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Exterior
Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!

Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!

Luray
10.0 out of 10, Exceptional, (188)
"Very peaceful place only 2.5 miles from Luray. Everything you need to cook a meal, a very comfortable bed, and a great view. I will most likely stay here again when I travel this way in the future. "
United States
Ellen C.
Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!
Outdoor dining
Dreamtime - Modern A-frame Cabin w/ Hot tub

Dreamtime - Modern A-frame Cabin w/ Hot tub

Berkeley Springs
10.0 out of 10, Exceptional, (50)
"Awesome place! Perfect for 4 people. Great long weekend!"
United States
Stephanie P.
The price is ￥46,091
￥58,648 total
includes taxes & fees
Dec 3 - Dec 4
Dreamtime - Modern A-frame Cabin w/ Hot tub
Exterior
Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray

Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray

2.0 star property
Luray
10.0 out of 10, Exceptional, (41)
"Great stay! "
United States
Kristen F.
The price is ￥48,529
￥89,349 total
includes taxes & fees
Nov 16 - Nov 17
Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray
Exterior
A Cozy Bear Cottage! Quiet Mountain Cabin!

A Cozy Bear Cottage! Quiet Mountain Cabin!

Luray
10.0 out of 10, Exceptional, (76)
"Great experience at the Cozy Bear Cottage. The cabin was just as described. Very comfortable and great communication from the host. "
United States
Jessica B.
A Cozy Bear Cottage! Quiet Mountain Cabin!
Property grounds
Cabin w New Hot Tub, River/Kayak, WiFi, & Fire Pit

Cabin w New Hot Tub, River/Kayak, WiFi, & Fire Pit

Great Cacapon
9.4 out of 10, Exceptional, (192)
"Overall a decent cabin. Think it’s probably best if you have a group or family of 6 looking for something economical. Seems like the cabin could use an overall refresh. Wish the hot tub was on the enclosed patio. "
United States
Brian
Cabin w New Hot Tub, River/Kayak, WiFi, & Fire Pit
Cabin, 1 Queen Bed, Mountain View | 1 bedroom, pillowtop beds, free WiFi, bed sheets
Canal Cabins

Canal Cabins

3.0 star property
Paw Paw
9.6 out of 10, Exceptional, (13)
"Great place for bikers to stay"
United States
mark
Canal Cabins
Outdoor spa tub
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

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

Rileyville
10.0 out of 10, Exceptional, (345)
"We had a great time at "Walden!" Beautiful location...Everything as advertised and more!! Plan to return...Highly recommend!! "
United States
Stephen D.
The price is ￥23,417
￥40,855 total
includes taxes & fees
Nov 18 - Nov 19
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Outdoor dining
Outdoor Theatre | Hot Tub | Fire Pit | Dogs

Outdoor Theatre | Hot Tub | Fire Pit | Dogs

Luray
9.8 out of 10, Exceptional, (56)
"Just as described online. Beautiful and secluded with great amenities. We really enjoyed our time there."
United States
Cheryl O.
The price is ￥15,261
￥46,908 total
includes taxes & fees
Dec 9 - Dec 10
Outdoor Theatre | Hot Tub | Fire Pit | Dogs
Exterior
Beautiful Private Cabin, adjacent to the National Forest

Beautiful Private Cabin, adjacent to the National Forest

Luray
9.8 out of 10, Exceptional, (136)
"Everything we hoped for in a weekend trip! The house smelled like cedar, was clean and very ample space. The hot tub was easy to operate; kitchen appliances helped cut down on eating out costs - would highly recommend and plan on making a reservation again!"
United States
Brieona C.
Beautiful Private Cabin, adjacent to the National Forest
1 bedroom, iron/ironing board, free WiFi, bed sheets
Silo Tiny House Cabin

Silo Tiny House Cabin

Harpers Ferry
9.6 out of 10, Exceptional, (8)
"Very nice place. Staying in a silo was a unique experience. It snowed while we were there and it was beautiful. We would definitely stay again. There is a lot to see and do in Harper's Ferry and the surrounding area."
United States
Teresa B.
The price is ￥27,038
￥45,534 total
includes taxes & fees
Nov 13 - Nov 14
Silo Tiny House Cabin
Smart TV, books
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

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

Luray
9.8 out of 10, Exceptional, (80)
"We had a great experience for a family wedding! The place was very clean and was in a great local spot that was easy to get to our wedding venue. "
United States
Rebecca W.
The price is ￥24,650
￥50,803 total
includes taxes & fees
Dec 7 - Dec 8
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Exterior
Private Log Cabin - Hot Tub, NEW SatelliteWi-Fi, Fireplace, Sm Pet Considered

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

Berkeley Springs
9.8 out of 10, Exceptional, (128)
"Everything was perfect Definitely recommended I liked that every room was climate controlled Very convenient "
United States
Donald C.
Private Log Cabin - Hot Tub, NEW SatelliteWi-Fi, Fireplace, Sm Pet Considered
Garden
Roadhaven 1830

Roadhaven 1830

3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (38)
"This cottage was super clean and cozy!!! The back yard was so relaxing with many games to keep adults and young kids entertained . I would highly recommend this place. I would live to stay again. The owner was very sweet also ❤️"
United States
Shirley
The price is ￥20,174
￥22,655 total
includes taxes & fees
Nov 13 - Nov 14
Roadhaven 1830
Property grounds
❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown
10.0 out of 10, Exceptional, (64)
"We truly loved this location and definitely will be back!"
United States
Astrid
The price is ￥6,239
￥16,293 total
includes taxes & fees
Nov 19 - Nov 20
❤️ Secluded 1940s Romantic Tiny House on the River
Exterior
Falling Leaf Cabin - Rustic Charm With Modern Decor!

Falling Leaf Cabin - Rustic Charm With Modern Decor!

Rileyville
9.8 out of 10, Exceptional, (302)
"Fallong Lead cabin is just the perfect little cabin. Everything you need to relax and unwind with gorgeous views and a wonderful hot tub. Looking forward to staying here again!!"
United States
Melissa R.
Falling Leaf Cabin - Rustic Charm With Modern Decor!
Terrace/patio
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks

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

Luray
10.0 out of 10, Exceptional, (13)
"Everything you need in this little space with easy access to deck with grill, fire pit and hot tub."
United States
Traci M.
The price is ￥22,693
￥37,501 total
includes taxes & fees
Nov 13 - Nov 14
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks
Pool
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

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

Rileyville
10.0 out of 10, Exceptional, (336)
"Excellent experience! The cabin was great, the location was great, the sights and people were great!"
United States
Tom A.
The price is ￥26,344
￥44,762 total
includes taxes & fees
Nov 25 - Nov 26
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

10/10 Excellent
"Nice place "
Phillip 2-night trip
Posted 22 hours ago
La Quinta Inn & Suites by Wyndham 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:

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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?

Half Round- A Quiet Mid-Century Modern Cabin: This vacation home rental near Winchester is located on a lake and has a fireplace, a patio, 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. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals will I find in Winchester?

Choose from 17 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.