Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (142)
"We really enjoyed the secluded location. It felt just far enough away but also easy to get to the cities nearby. We had a few issues with bugs, but nothing unexpected for mountain life. The kitchen was well stocked and the wifi worked surprisingly well during our stay. This was great for our girls trip and we would definitely come here again!"
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Property grounds
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
9.6 out of 10, Exceptional, (151)
"We enjoyed the home but the land even more. Nature is awesome!"
Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI
Garden
Family Farmhouse Inn
3.0 star property
9.6 out of 10, Exceptional, (25)
"excellent "
The price is €126
per night
23 May - 24 May
Family Farmhouse Inn
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TV, fireplace, books, stereo
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
9.6 out of 10, Exceptional, (8)
"Beautiful property, quiet, and very spacious. This property had everything we were looking for in a getaway. My family enjoyed our time together here. We did have a power outage and I let Tony know as soon as the power went out. He was quick to respond and even gave updates. Loved the communication from Tony throughout our whole experience. Definitely would stay here again and at another one of his properties."
The price is €282
per night
29 May - 30 May
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
2 bedrooms, WiFi, bed sheets
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
9.8 out of 10, Exceptional, (265)
"The place is amazing, great view to the river, night view is gorgeous, my kids had a lot of fun here, we will come back"
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
Exterior
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
9.8 out of 10, Exceptional, (244)
"We really enjoyed the property. It was clean. Internet worked well. Washer and dryer was nice. Too cold to enjoy the hot tub for me. My suggestions are a new shower head, thank goodness I didn’t have to wash my hair. The flow is too spread out and not enough to efficiently rinse as you shower. Second is a cheaper Kcup machine would be nice. Traveling with ground coffee is not really ideal for a quick trip away. Third thing I suggest is two beach towels (minimum) for the use of the hot tub. We...
The price is €295
per night
27 May - 28 May
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Property grounds
Riverside cottage, minutes from historic Harpers Ferry; private river access!
9.8 out of 10, Exceptional, (56)
"It was farther from Harper’s Ferry then I expected. However to location was beautiful."
The price is €209
per night
2 Jun - 3 Jun
Riverside cottage, minutes from historic Harpers Ferry; private river access!
Property grounds
Dreamtime - Modern A-frame Cabin w/ Hot tub
10.0 out of 10, Exceptional, (26)
"Cabin was amazing. Definitely would go back!"
Dreamtime - Modern A-frame Cabin w/ Hot tub
Smart TV, DVD player, books, video library
Cozy Mountain Cabin w/ Steam Shower! Family Friendly!
10.0 out of 10, Exceptional, (28)
"Very nice clean cabin in a very quiet location. enjoyed our stay watching the deer come by everyday and other wildlife."
The price is €311
per night
23 May - 24 May
Cozy Mountain Cabin w/ Steam Shower! Family Friendly!
Interior
Escape to Shenandoah River, Hot Tub after a Hike!
10.0 out of 10, Exceptional, (38)
"Super clean. Super easy check in & check out. Quiet and beautiful setting. The windows bring the outdoors in. Fabulous to watch the electric storm through those big beautiful windows from the comfort of the couch."
The price is €352
per night
5 Jun - 6 Jun
Escape to Shenandoah River, Hot Tub after a Hike!
Interior
Lake House w/ Pool and King Bed, Fishing - Dogs OK
10.0 out of 10, Exceptional, (12)
"We enjoyed our stay, really nice place we enjoyed seeing the water"
Lake House w/ Pool and King Bed, Fishing - Dogs OK
2 bedrooms, WiFi, bed sheets
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
9.4 out of 10, Exceptional, (297)
"The description was accurate and the view was very nice. There was a small glitch regarding linens when we checked in but John worked with us to fix it. Overall we enjoyed our stay"
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
View from property
RIVERKEEPER INN, Waterfront Property on the Potomac River
9.4 out of 10, Exceptional, (104)
"Sweet place! We brought out dog, and it felt like a second home - safe, beautiful, and easy."
RIVERKEEPER INN, Waterfront Property on the Potomac River
Pool
"Solitude" Secluded 1 BR Cabin w/ Hot Tub near Luray, VA.
10.0 out of 10, Exceptional, (273)
"Our stay was very relaxed, the property is in a nice location, nestled in the woods, with a nice amount of lawn in the front. We enjoyed the wildlife, and explored Luray caverns and some of the Shenandoah mountains. The cabin is very simple, but sufficient, and has essentials, although a cabinet somewhere would have been convenient. Thank you for making our great week possible, it was a blessing!"
The price is €315
per night
27 May - 28 May
"Solitude" Secluded 1 BR Cabin w/ Hot Tub near Luray, VA.
Exterior
18th Century Stone Cottage minutes from historic Middleburg
10.0 out of 10, Exceptional, (16)
"We had a nice stay in a lovely rural location with nice outdoor terrace and quiet street for a long walk. Communication with the host was simple and straight forward."
The price is €369
per night
9 Jun - 10 Jun
18th Century Stone Cottage minutes from historic Middleburg
Property grounds
Hidden Gem in the woods with hot tub
9.6 out of 10, Exceptional, (49)
"We really enjoyed our stay! The hot tub, game room, fire pit, and smart TV were all great! It was a beautiful woodsy getaway for sure and it was peaceful."
Hidden Gem in the woods with hot tub
Fridge, microwave, oven, stovetop
Secluded Pet-Friendly High-Tech Log Cabin in the Woods
9.6 out of 10, Exceptional, (149)
"great spot for a get a way. highly recommend the baths in town."
Secluded Pet-Friendly High-Tech Log Cabin in the Woods
Property grounds
Secluded Mountain Cabin with Spectacular Views- Hiker's Dream
10.0 out of 10, Exceptional, (25)
"The pictures and description are 100% accurate, but being there in person to take in the peaceful surroundings and views of nature with the family was a great experience. The hostess was responsive from the moment we booked and provided all the info we needed to make it to this mountain top cabin on the VA/WV border. We drove up on a Friday and after getting out of DC traffic we were on our way to Almost Heaven cabin. When we’re about a mile or so from the cabin we saw a black bear crossing...
Secluded Mountain Cabin with Spectacular Views- Hiker's Dream
Fridge, microwave, oven, stovetop
Breathtaking views with an indoor private pool, come escape with us
9.8 out of 10, Exceptional, (227)
"Fantastic spot to spend a few days. Incredible house, fantastic amenities, and a beautiful location."
Breathtaking views with an indoor private pool, come escape with us
Property grounds
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (188)
"Beautiful quiet location. Very close to the forest, but unfortunately there is a large stream that runs across the trail that leads to GWNF. Otherwise, a nearly perfect place! The host's communication was great as well. We enjoyed the pool table (can be table tennis as well), and the variety of hikes a short drive away. Some of the furniture had animal hair on it from a previous guest. A deeper clean would have been appreciated, but it wasn't a major concern. We will consider visiting again in...
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Don't see what you're looking for?
See all available properties in 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.

Other types of properties in Winchester you may be interested in

Exterior
La Quinta Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (1339)
"Beautiful !!! Way exceeded expectations ! Great price and gorgeous and clean rooms very modern layout ! Beautiful breakfast and pleasant staff. What a pleasure !!! "
The price is €118
per night
27 May - 28 May
La Quinta Inn & Suites by Wyndham Winchester
Lobby
Microtel Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (770)
"Pool is cold, staff is super nice. Place is clean and very nice lots near it for food mall is only 8 min away. Breakfast was ok. Have stayed here several times and will continue to stay here as needed."
The price is €84
per night
2 Jun - 3 Jun
Microtel Inn & Suites by Wyndham Winchester
Seasonal outdoor pool
Travelodge by Wyndham Winchester
2.5 star property
8.0 out of 10, Very good, (1064)
"nice place, clean but in desperate need of update."
The price is €69
per night
28 May - 29 May
Travelodge 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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winchester holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as €126 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester holiday 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 holiday.

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 holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Shenandoah Valley Discovery Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theatre scene while you're visiting.

How many holiday rentals will I find in Winchester?

Choose from 13 Expedia holiday rentals in Winchester for a memorable holiday.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Nalls Farm Market are a couple of the family-friendly sights, whereas cultural attractions include Museum of the Shenandoah Valley and Bright Box Theater. Other places in town to visit include Jim Barnett Park and Apple Blossom Mall.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family getaway.

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