Winchester Vacation Rentals

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Check prices for these dates

Tonight
Jul 18 - Jul 19
Tomorrow
Jul 19 - Jul 20
This weekend
Jul 18 - Jul 20
Next weekend
Jul 25 - Jul 27

Vacation Rentals in Winchester

Canal Cabins
Cozy cabin-style room with a large bed, kitchenette, and TV.

Canal Cabins

3.0 star property
10.0 out of 10, Exceptional, (4)
"All was expected. Nice Cabins"
The price is CA $167
CA $189 total
includes taxes & fees
Aug 18 - Aug 19
Canal Cabins
Dreamtime - Modern A-frame Cabin w/ Hot tub
Escape to a serene forest retreat with a cabin-style home featuring a spacious deck and a relaxing hot tub.

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (45)
"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
Sit and enjoy the view from this outdoor seating area with a round table and two chairs.

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

9.8 out of 10, Exceptional, (292)
"We stayed just 2 nights and absolutely loved it. Totally going back again! "
The price is CA $275
CA $436 total
includes taxes & fees
Aug 10 - Aug 11
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Star view cabin-Riverfront
Relax on the deck with Adirondack chairs and a potted plant, taking in the views of the lush landscape and distant mountains.

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (322)
"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*
Relax in this inviting living room with a comfortable sofa, armchairs, and a flat-screen TV.

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

10.0 out of 10, Exceptional, (67)
"Sweet l, well located property with everything you need for a stay! "
The price is CA $201
CA $427 total
includes taxes & fees
Jul 21 - Jul 22
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Secluded River Cabin Getaway (Masten Cabin)
Enjoy cooking in this kitchen with a large window offering a view of the outdoors, featuring a sink, stove, microwave, and refrigerator.

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
Relax in a serene hot tub under a shaded pergola with a breathtaking view of the snowy landscape.

"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 CA $216
CA $376 total
includes taxes & fees
Jul 20 - Jul 21
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Charming Cabin in the Woods with River Access
Guests can enjoy a peaceful retreat in this cabin-style building, featuring a spacious porch and easy access to the surrounding woods.

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (27)
"Very nice rest time…"
The price is CA $224
CA $406 total
includes taxes & fees
Jul 27 - Jul 28
Charming Cabin in the Woods with River Access
Lookout Cabin in the mountains, Amazing Views!
Relax in a hot tub on a spacious deck with a breathtaking view of rolling hills.

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 CA $263
CA $499 total
includes taxes & fees
Jul 20 - Jul 21
Lookout Cabin in the mountains, Amazing Views!
Summer at A Cozy Bear Cottage! New Furniture & lamps/lighting!
Cozy cabin with a porch and stairs, surrounded by a well-maintained lawn and trees.

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

10.0 out of 10, Exceptional, (64)
Summer at A Cozy Bear Cottage! New Furniture & lamps/lighting!
Falling Leaf Cabin - Rustic Charm With Modern Decor!
Escape to a cozy cabin surrounded by nature, featuring a steeply pitched roof, chimney, and inviting front porch.

Falling Leaf Cabin - Rustic Charm With Modern Decor!

9.8 out of 10, Exceptional, (289)
"Exceeded expectations."
Falling Leaf Cabin - Rustic Charm With Modern Decor!
Cottage on King | Charming Historic Leesburg Home
Relax in this inviting outdoor seating area with sofas, armchairs, and a central table featuring a fire feature.

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (52)
The price is CA $239
CA $476 total
includes taxes & fees
Aug 11 - Aug 12
Cottage on King | Charming Historic Leesburg Home
Family Farmhouse Inn
Relax in a serene garden setting with a shaded deck, comfortable seating, and a charming gazebo.

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 CA $177
CA $198 total
includes taxes & fees
Jul 27 - Jul 28
Family Farmhouse Inn
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Enjoy the serene forest views from this outdoor deck, featuring a round table and comfortable seating.

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
Relax in a serene outdoor setting with a bubbling hot tub surrounded by lush greenery and a deck.

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

9.8 out of 10, Exceptional, (58)
"Clean, well appointed cabin. Good communication"
Riverfront🏕A-Frame/HOT TUB/Fire Pit! FAST Wifi
Quaint Loft Cabin w/Hot Tub, FirePit, Deck & Grill
Cozy living area with a long table, sofa, and TV, plus a kitchen with modern appliances and cabinetry.

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

9.2 out of 10, Wonderful, (7)
"We had a great time in West Virginia and the Chalet. The properry was well maintained and the host was very proactive with checking in to see if we arrived and got inside without incident, and to see if we needed anythjng. "
The price is CA $205
CA $367 total
includes taxes & fees
Jul 30 - Jul 31
Quaint Loft Cabin w/Hot Tub, FirePit, Deck & Grill
Private Log Cabin - Hot Tub, NEW SatelliteWi-Fi, Fireplace, Sm Pet Considered
Guests can enjoy a balcony with a railing, offering a view of the surrounding forest.

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
Guests can enjoy a serene outdoor setting surrounded by mature trees and a clear sky.

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

9.6 out of 10, Exceptional, (185)
"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!
Enjoy a panoramic view of the lush landscape from the large, arched window in this spacious room.

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.
Enjoy a peaceful retreat in this cabin with a balcony and covered porch, surrounded by trees.

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 CA $186
CA $498 total
includes taxes & fees
Jul 22 - Jul 23
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 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?

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly: This vacation home rental 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. Kitchen amenities include a dishwasher, a fridge, and a stovetop. 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 19 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 Museum of the Shenandoah Valley. Other places in town to visit include Patsy Cline Historic House and Jim Barnett Park.

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.