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Winchester Vacation Rentals

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Vacation Rentals in Winchester

❤️ Secluded 1940s Romantic Tiny House on the River
The price is $65 per night from Jun 6 to Jun 7
$65
per night
Jun 6 - Jun 7
Stay at this cabin in Shepherdstown. Enjoy free WiFi, onsite parking, and a porch. Our guests praise the comfy beds and the overall value in our reviews. Popular ...
9.6/10 Exceptional! (26 reviews)
Heaven!
"Imagine… perfect!"

Reviewed on May 24, 2023

❤️ Secluded 1940s Romantic Tiny House on the River
Dreamtime - Modern A-frame Cabin w/ Hot tub
Stay at this cabin in Berkeley Springs. Enjoy free WiFi, onsite parking, and barbecue grills. Popular attractions Frog Valley Artisans, LTD and Colonial Springs ...
10/10 Exceptional! (20 reviews)
Beautiful Cabin in the woods!
"We enjoyed our stay so much! The cabin is beautiful and situated in a great neighborhood with trails pretty much right outside the door! Easy drive to the brewery, winery and to downtown for restaurants and site seeing!"

Reviewed on May 20, 2023

Dreamtime - Modern A-frame Cabin w/ Hot tub
Falling Leaf Cabin Secluded With Mountain View!
Stay at this family-friendly cabin in Rileyville. Enjoy WiFi, a patio, and a Smart TV. Our guests praise the comfy rooms in our reviews. Popular attraction Elkwallow ...
9.6/10 Exceptional! (211 reviews)
Beautiful cabin
"This was exactly what my wife and I needed to relax and unwind. Cabin looks small on the outside but looks are deceiving. The layout and design was perfect and allows each space to feel open and comfortable. Only thing I’d say is the view has potential to be awe inspiring if some of the overgrowth ..."

Reviewed on May 19, 2023

Falling Leaf Cabin Secluded With Mountain View!

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Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Stay at this family-friendly vacation home in Star Tannery. Enjoy WiFi, onsite parking, and an arcade/game room. Our guests praise the family amenities in our ...
9.6/10 Exceptional! (167 reviews)
Remote cabin,
"This cabin is lovely, it's cozy & I loved the fireplace and a large deck. It's also pretty well stoked. It's remote, which can be a plus if you want to get away from the crowds, but it takes a while to get in and out the area if you want to go places. The gravel road leading to the house is in great ..."

Reviewed on May 18, 2023

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Charming mountaintop cabin with hot tub, pool table, and breathtaking views
Stay at this vacation home in Great Cacapon. Enjoy WiFi, an arcade/game room, and a garden. Popular attractions Frog Valley Artisans, LTD and Prospect Peak are ...
9.8/10 Exceptional! (139 reviews)
Beautiful mountain views
"We had such an amazing time at the cabin. The view was beautiful and we enjoyed the hot tub. It was exactly what we were looking for."

Reviewed on May 2, 2023

Charming mountaintop cabin with hot tub, pool table, and breathtaking views
Breathtaking views  with an  indoor private pool, come escape with us
Stay at this vacation home in Bluemont. Enjoy private pools, WiFi, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular ...
9.6/10 Exceptional! (187 reviews)
Stay at bear chase manor
"Always wanted to stay at this property and loved it!"

Reviewed on May 26, 2023

Breathtaking views with an indoor private pool, come escape with us
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Stay at this family-friendly vacation home in Star Tannery. Enjoy free WiFi, onsite parking, and an arcade/game room. Discover genuine guest reviews for Adorable ...
9.8/10 Exceptional! (107 reviews)
Best stay by 200%.
"Absolutely the best stay. 200% better than we expected. Perfect!!!"

Reviewed on May 22, 2023

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
1760s Cabin
Lovettsville, VA
The price is $98 per night from Jun 1 to Jun 2
$98
per night
Jun 1 - Jun 2
Stay at this cabin in Lovettsville. Enjoy free WiFi, onsite parking, and a garden. Popular attractions Hiddencroft Vineyards and Catoctin Valley are located ...
9.8/10 Exceptional! (9 reviews)
Great place!
"The cabin itself is wonderful, and has so much character. The property owners have done remarkable things with it. The only negative I can speak to is that we thought it was out on a farm more remote from the main house. It’s actually located in more of a neighborhood in the yard of the property ..."

Reviewed on May 21, 2023

1760s Cabin
Cozy riverfront cabin on the Shenandoah
Stay at this family-friendly cabin in Luray. Enjoy free WiFi, onsite parking, and a garden. Popular attraction Seven Bends State Park is located nearby. Discover ...
9.8/10 Exceptional! (145 reviews)
Great place
"Great place on the river. Spacious. Comfortable everything. Everything was as advertised. Thank you!"

Reviewed on May 15, 2023

Cozy riverfront cabin on the Shenandoah
NEW! Peaceful Hideaway w/ Shenandoah River Access
Stay at this vacation home in Bluemont. Enjoy a garden, barbecue grills, and a patio. Popular attractions Watermelon Park Campground and Veramar Vineyard are ...
8.8/10 Excellent! (18 reviews)
Beautiful house and property
"My family and I were looking for a quick little getaway house with plenty of running space for our fur babies and just enough space for us to spend quality time together. The river across the road is beautiful and serene and the creek in the woods next to the house is like a dream. The homeowner ..."

Reviewed on May 20, 2023

NEW! Peaceful Hideaway w/ Shenandoah River Access
"Solitude" Spectacular 1 BR Cabin w/ Hot Tub near Luray, VA.
Stay at this cabin in Rileyville. Enjoy free WiFi, onsite parking, and a garden. Popular attraction Elkwallow Picnic Area is located nearby. Discover genuine ...
10/10 Exceptional! (214 reviews)
The name says it all
"This cabin was perfect for a spring retreat on my own. The kitchen was well equipped, the bedroom and living room were comfortable. The cabin sits on a beautiful hillside under tall pines, and was quiet and peaceful. I spent the weekend hiking in SNP, cooking, and relaxing at the cabin."

Reviewed on May 27, 2023

"Solitude" Spectacular 1 BR Cabin w/ Hot Tub near Luray, VA.
Blue Ridge Getaway - Mountaintop Cabin with Sunset Views, Just 300 yards from the A.T.!
Stay at this cabin in Harpers Ferry. Enjoy free WiFi, onsite parking, and a porch. Popular attractions Shenandoah Lake Beach and 868 Estate Vineyards are located ...
10/10 Exceptional! (26 reviews)
Great experience with beautiful views!
"The property was awesome, very well equipped, clean, comfy beds and pillows! So the rest is FYI. We loved it and would stay here again definitely! The property location is a little of a double edged sword. It's very private and as mentioned in the title, the views are amazing! But it's about 15 minutes ..."

Reviewed on Apr 24, 2023

Blue Ridge Getaway - Mountaintop Cabin with Sunset Views, Just 300 yards from the A.T.!
Star view cabin-Riverfront
Stay at this cabin in Rileyville. Enjoy WiFi, onsite parking, and an in-room DVD player. Our guests praise the WiFi and the property condition in our reviews. ...
9.8/10 Exceptional! (205 reviews)
Great stay!
"We had an incredible time at this property! The views were incredible and it’s an easy drive to the park and great outdoors activities. Everything in the house was clean and they had everything we needed for a good weekend trip."

Reviewed on May 3, 2023

Star view cabin-Riverfront
Cozy Lakeside Homestead
Wardensville, WV
The price is $210 per night from Jun 18 to Jun 19
$210
per night
Jun 18 - Jun 19
Stay at this family-friendly vacation home in Wardensville. Enjoy free WiFi, a sauna, and onsite parking. Our guests praise the bathrooms in our reviews. Popular ...
10/10 Exceptional! (137 reviews)
Quiet Retreat in Mountain Woods
"Single-level home, big yard near wooded mountain slope, huge great room, lots of wildlife & birds. Can see small lake. Wardensville, VA does have a grocery store, but very limited choice for restaurants."

Reviewed on May 19, 2023

Cozy Lakeside Homestead
Secluded River Cabin Getaway (Masten Cabin)
Stay at this vacation home in Strasburg. Enjoy free WiFi, onsite parking, and barbecue grills. Popular attractions Secret Passage Ranch and Strasburg Museum ...
9.8/10 Exceptional! (92 reviews)
Perfect
"Very cozy and clean"

Reviewed on May 16, 2023

Secluded River Cabin Getaway (Masten Cabin)
Art Docko - Lakefront Artists' Retreat for a Relaxing Getaway!
The price is $284 per night from Jun 1 to Jun 2
$284
per night
Jun 1 - Jun 2
Stay at this cottage in Harpers Ferry. Enjoy free WiFi, a Smart TV, and 4 bathrooms. Popular attractions Shenandoah Lake Beach and K & S Pewter are located nearby. ...
10/10 Exceptional! (3 reviews)
This house is a gem!
"This house is modern and sits on a beautiful lake. Top of the line architecture and is fully equipped."

Reviewed on Apr 20, 2023

Art Docko - Lakefront Artists' Retreat for a Relaxing Getaway!
Lost River Luxury Cabin in Wild Wonderful West Virginia-2 hour drive fr DC!
Stay at this cabin in Baker. Enjoy WiFi, onsite parking, and a garden. Popular attractions Lost River and Lost River Artisans Cooperative are located nearby. ...
10/10 Exceptional! (40 reviews)
Easter break with grandson
"First, I appreciate Stacey answering all my questions, and making the whole process simple. Not only was the communication great (& friendly) the house had all my “wants” which is not usually the case. Very soft/cozy sofas to lounge in, uncomplicated TVs, decks with a view & rocking chairs, fireplace ..."

Reviewed on Apr 17, 2023

Lost River Luxury Cabin in Wild Wonderful West Virginia-2 hour drive fr DC!
New! Sapphire Ridge | Escape to Shenandoah River | Hot Tub!
Stay at this cabin in Front Royal. Enjoy WiFi, a patio, and 3 bedrooms. Popular attractions Shenandoah River and Tuckers Lane Trailhead are located nearby. Discover ...
10/10 Exceptional! (4 reviews)
Great mountain stay
"Kayla’s house was clean and comfy, and Kayla was a very responsive host. We very much enjoyed our stay!"

Reviewed on Apr 23, 2023

New! Sapphire Ridge | Escape to Shenandoah River | Hot Tub!
*Harper's Ferry Hideaway*
Harpers Ferry, WV
Stay at this vacation home in Harpers Ferry. Enjoy free WiFi, onsite parking, and a garden. Popular attractions Notaviva Vineyards and Shenandoah Lake Beach ...
8/10 Very Good! (20 reviews)
Cute!!
"Loved our stay, such a beautiful area!"

Reviewed on Dec 12, 2022

*Harper's Ferry Hideaway*
"The Chalet" Shenandoah Valley Getaway w/ Hot Tub near Luray, VA
Stay at this family-friendly cabin in Rileyville. Enjoy free WiFi, onsite parking, and barbecue grills. Popular attraction Elkwallow Picnic Area is located nearby. ...
9.8/10 Exceptional! (223 reviews)
Great stay!
"This was the perfect place for a quick family vacation!"

Reviewed on May 25, 2023

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

Other types of properties in Winchester you may be interested in

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA, 22602
Fully refundableReserve now, pay when you stay
Travelodge by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA, 22602
Fully refundableReserve now, pay when you stay
La Quinta Inn & Suites by Wyndham Winchester
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.

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $60 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails: This vacation home rental near Winchester is located in a rural location 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. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Winchester?

Choose from 10 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 Shenandoah National Park and Patsy Cline Historic House.

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.

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