Winchester Vacation Rentals

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Check prices for these dates

Tonight
Jun 28 - Jun 29
Tomorrow
Jun 29 - Jun 30
Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13

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, (2)
"All was expected. Nice Cabins"
The price is ￥16,266
￥18,380 total
includes taxes & fees
Jul 5 - Jul 6
Canal Cabins
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, (34)
"We enjoyed our stay here."
Private, light filled retreat space... with your own pickleball court!
Dreamtime - Modern A-frame Cabin w/ Hot tub
Outdoor dining

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 ￥41,804
￥52,494 total
includes taxes & fees
Jul 24 - Jul 25
Dreamtime - Modern A-frame Cabin w/ Hot tub
Log Cabin w Loft, Hot Tub, Deck, Fire Pit, & WiFi
Terrace/patio

Log Cabin w Loft, Hot Tub, Deck, Fire Pit, & WiFi

9.0 out of 10, Wonderful, (22)
"It was wonderful and peaceful"
The price is ￥32,445
￥51,605 total
includes taxes & fees
Jun 29 - Jun 30
Log Cabin w Loft, Hot Tub, Deck, Fire Pit, & WiFi
Secluded River Cabin Getaway (Masten Cabin)
Fridge, microwave, oven, stovetop

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)
Charming Cabin in the Woods with River Access
Exterior

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 ￥23,578
￥43,618 total
includes taxes & fees
Jul 20 - Jul 21
Charming Cabin in the Woods with River Access
A Cozy Bear Cottage! Clean and Quiet!!
Exterior

A Cozy Bear Cottage! Clean and Quiet!!

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. "
A Cozy Bear Cottage! Clean and Quiet!!
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Property grounds

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

9.8 out of 10, Exceptional, (289)
"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 ￥24,073
￥41,093 total
includes taxes & fees
Jul 1 - Jul 2
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
"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, (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 ￥24,735
￥42,196 total
includes taxes & fees
Jul 2 - Jul 3
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub
Outdoor Theatre | Hot Tub | Fire Pit | Dogs
Outdoor dining

Outdoor Theatre | Hot Tub | Fire Pit | Dogs

10.0 out of 10, Exceptional, (43)
"It was a amazing stay"
The price is ￥16,345
￥47,205 total
includes taxes & fees
Jun 30 - Jul 1
Outdoor Theatre | Hot Tub | Fire Pit | Dogs
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly
Outdoor spa tub

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

9.6 out of 10, Exceptional, (181)
"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
Star view cabin-Riverfront
Property grounds

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
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 ￥18,651
￥20,946 total
includes taxes & fees
Jul 2 - Jul 3
Family Farmhouse Inn
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, (122)
"Great location to hiking trails and Harper’s Ferry National Park, shops, and restaurants. Charming, cozy house with a great sense of history, complete with wonky angles and creaky floorboards. Gas fireplace is a nice bonus."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
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, (315)
"Beautiful cabin and spectacular location. Highly recommended for a great escape. Loved it!!!"
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
Grill, Fire Pit, WiFi, Deck, Hammock, Games & Dogs
TV, offices

Grill, Fire Pit, WiFi, Deck, Hammock, Games & Dogs

8.8 out of 10, Excellent, (3)
"Found this cabin to be cute and comfortable. Nice surroundings with deer, turtles, birds and squirrel. Would return again! "
The price is ￥22,887
￥47,474 total
includes taxes & fees
Jul 10 - Jul 11
Grill, Fire Pit, WiFi, Deck, Hammock, Games & Dogs
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Miscellaneous

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

10.0 out of 10, Exceptional, (373)
"My family and I enjoyed our week in the Shenandoah Valley. This property had everything we needed to enjoy meals together and quality family time in the evening. There was so much to do in the area. We would definitely love to visit again "
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
Property grounds

Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

10.0 out of 10, Exceptional, (42)
"Great getaway location. Beautiful property"
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>
RIVERKEEPER INN, Waterfront Property on the Potomac River
Terrace/patio

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (121)
"Riverkeeper Inn is located in a peaceful and quiet area of Harpers Ferry, equally perfect in early mornings and late nights. The check-in and check-out process were very easy, and the property itself had everything we could've asked for, and then some."
RIVERKEEPER INN, Waterfront Property on the Potomac River
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, (64)
"Very nice updated house 20 minutes from Shenandoah Park. "
The price is ￥20,830
￥44,697 total
includes taxes & fees
Jun 29 - Jun 30
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*
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 20 Expedia vacation rentals in Winchester for a memorable vacation.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Rocking S Ranch 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.