Winchester Vacation Rentals

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Check prices for these dates

Tonight
Jul 24 - Jul 25
Tomorrow
Jul 25 - Jul 26
This weekend
Jul 25 - Jul 27
Next weekend
Aug 1 - Aug 3

Vacation Rentals in Winchester

Canal Cabins
Cabin, 1 Queen Bed, Mountain View | 1 bedroom, pillowtop beds, free WiFi, bed sheets

Canal Cabins

3.0 star property
10.0 out of 10, Exceptional, (4)
"All was expected. Nice Cabins"
The price is ￥17,758
￥20,067 total
includes taxes & fees
Jul 29 - Jul 30
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, (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, "
The price is ￥43,789
￥55,098 total
includes taxes & fees
Aug 24 - Aug 25
Dreamtime - Modern A-frame Cabin w/ Hot tub
Star view cabin-Riverfront
Property grounds

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (323)
"This was absolutely just what we needed! The view was so breathtaking and the serenity of this place is to die for! I was very pleased with our stay here and we will definitely be returning de"
Star view cabin-Riverfront
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Exterior detail

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

10.0 out of 10, Exceptional, (125)
"The view from the porch, accessibility to food, good coffee, hikes, shops, and important history, are unmatched. Our hosts are kind and accommodating. This is our second time here and won't be our last. "
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
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, (68)
"Sweet l, well located property with everything you need for a stay! "
The price is ￥22,802
￥46,555 total
includes taxes & fees
Aug 3 - Aug 4
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
Falling Leaf Cabin - Rustic Charm With Modern Decor!
Exterior

Falling Leaf Cabin - Rustic Charm With Modern Decor!

9.8 out of 10, Exceptional, (290)
"Great location! It provided the perfect space to unwind. I image the view changes with each season, but always beautiful with a feeling of privacy. "
Falling Leaf Cabin - Rustic Charm With Modern Decor!
"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)
"we were looking for a quiet get away, loved having our 16YO boy more interested in fishing and hiking then sitting on his Xbox! We all really loved how quiet and calm it was, definitely plan on going back"
The price is ￥21,748
￥38,079 total
includes taxes & fees
Jul 28 - Jul 29
"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)
"Very nice rest time…"
The price is ￥23,871
￥44,005 total
includes taxes & fees
Jul 27 - Jul 28
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 ￥32,600
￥60,623 total
includes taxes & fees
Jul 27 - Jul 28
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, (64)
"We enjoyed our stay in this cabin. Lots of fun hiking in the National Park nearby. We loved sitting by the firepit in the evenings. The cabin was very clean and well-stocked with everything we needed. "
Summer at A Cozy Bear Cottage! New Furniture & lamps/lighting!
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 ￥18,892
￥21,216 total
includes taxes & fees
Aug 2 - Aug 3
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, (89)
"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, (59)
"Loved everything about this property! So quiet and peaceful. My husband and I needed time to reconnect and connect with nature and this was the place to do it!"
Riverfront🏕A-Frame/HOT TUB/Fire Pit! FAST Wifi
Beautiful Private Cabin, adjacent to the National Forest
Exterior

Beautiful Private Cabin, adjacent to the National Forest

9.8 out of 10, Exceptional, (129)
"Peaceful and wonderful. Well appointed and very clean"
Beautiful Private Cabin, adjacent to the National Forest
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
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, (38)
"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!
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, (186)
"The highlight of the rental for us was definitely the property. We loved the view and our kids enjoyed wading in the river. Hot tub was great after days spent hiking in Shenandoah! "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
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 ￥13,181
￥44,800 total
includes taxes & fees
Jul 28 - Jul 29
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
2 bedrooms, WiFi, bed sheets

Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

9.6 out of 10, Exceptional, (320)
"Very clean with amazing views. "
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.
Pool

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

10.0 out of 10, Exceptional, (320)
"This is, I believe, my fourth time staying at Solitude. I keep coming back because it is perfect. "
The price is ￥25,629
￥42,721 total
includes taxes & fees
Aug 3 - Aug 4
"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

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

10/10 Excellent
"Overall very good experience."
willy 1-night trip
Posted 20 hours ago
Holiday Inn Winchester Se-Historic Gateway by IHG

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?

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!: This vacation home rental near Winchester is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the private yard in this rental home to help you unwind.

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 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.