Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Exterior
Updated! Stunning country home near main street
10.0 out of 10, Exceptional, (32)
"Awesome house just outside of town. The place was spotless & well-appointed. Fantastic spot if you travel with your canine family. We had a lovely meal at the Watch & Warrant. Would stay here again without hesitation."
The price is €296
per night
6 May - 7 May
Updated! Stunning country home near main street
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
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, (262)
"Property has a great view and is in a convenient location to town and Shenandoah NP. Would stay again!"
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
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Property grounds
Riverside cottage, minutes from historic Harpers Ferry; private river access!
9.8 out of 10, Exceptional, (54)
"We came into town to see a show at Charles Town Casino. The location was perfect! We loved the view of the river. The home was very clean, comfortable and well appointed. We enjoyed a great dinner at Mi Dellagado and an excellent breakfast at the Mountain View Diner. We would definitely stay here again when we are in the area."
The price is €210
per night
6 May - 7 May
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!"
The price is €356
per night
6 May - 7 May
Dreamtime - Modern A-frame Cabin w/ Hot tub
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
9.8 out of 10, Exceptional, (140)
"Nice place to be sort of off the grid."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Property grounds
Star view cabin-Riverfront
9.8 out of 10, Exceptional, (274)
"My husband and I stayed for a short weekend away from the city. This place is the perfect place to disconnect and surround yourself with nature and beautiful views. Only suggestion that I have for guests is to be sure you bring towels, cooking oil, extra paper towells, and coffee/tea of your choice. Otherwise, everything is provided!"
Star view cabin-Riverfront
2 bedrooms, WiFi, bed sheets
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
9.4 out of 10, Exceptional, (296)
"Recently stayed the cozy cabin for a delightful weekend in the mountains. The cabin is lovely, especially the new master suite, bathroom, and beautiful wrap around deck. There’s almost no need to go anywhere, just sit and enjoy the views, the fireplace, and lovely location. That said, it’s super easy to get to Shenandoah and Front Royal as well, making it a perfect landing spot for activities in the region. I would definitely stay there again and highly recommend."
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Outdoor dining
Bear Valley- Riverfront with hot tub!
9.8 out of 10, Exceptional, (97)
"We came here for a quick Spring Break trip with our boys and dogs. We loved the view in the mornings and the hot tub was very relaxing!"
Bear Valley- Riverfront with hot tub!
Property grounds
Charming mountaintop cabin with hot tub, pool table, and breathtaking views
9.8 out of 10, Exceptional, (168)
"Charming is the perfect word for this cozy cabin. From the exceptional amenities to the perfect view, this place was a dream come true."
Charming mountaintop cabin with hot tub, pool table, and breathtaking views
Garden
Family Farmhouse Inn
3.0 star property
9.6 out of 10, Exceptional, (24)
"excellent "
The price is €133
per night
9 May - 10 May
Family Farmhouse Inn
Exterior
Lovely home, wonderful location.
10.0 out of 10, Exceptional, (46)
"Quaint cottage with comfortable living space and bonus outdoor lounge chairs to enjoy an afternoon book. The property is within 30 mins of hiking trails in Shenandoah National Park. We really appreciated the ability to get to Main Street high end restaurants and an ice cream shop that had delicious flavor choices. We enjoyed ourselves and the owner was quick responding to questions. "
The price is €283
per night
6 May - 7 May
Lovely home, wonderful location.
Property grounds
Family-friendly waterfront cabin with great views & canoes/kayaks. Pets welcome!
10.0 out of 10, Exceptional, (168)
"Small mouth fishing is great! Property was clean and had nice amenities. Would recommend the stay here for a family"
Family-friendly waterfront cabin with great views & canoes/kayaks. Pets welcome!
Pool
"Solitude" Secluded 1 BR Cabin w/ Hot Tub near Luray, VA.
10.0 out of 10, Exceptional, (271)
"Wonderful property! Super clean and welcoming! Very secluded and provided everything we needed to be able to decompress and relax!"
The price is €317
per night
27 May - 28 May
"Solitude" Secluded 1 BR Cabin w/ Hot Tub near Luray, VA.
Property grounds
Hidden Gem in the woods with hot tub
9.6 out of 10, Exceptional, (48)
"Overall we had a great couple of nights away. It was super quiet and just a short drive from the town of Berkeley Springs. We loved the game room, fire pit, hot tub and overall just the quiet of being tucked away in the woods. We did communicate to Michael that the hot tub was a little dirty when we opened it and the shower lacked pressure and he was responsive and said he would take care of them. responsive when we raised a couple of issues and said he"
Hidden Gem in the woods with hot tub
Exterior
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
9.8 out of 10, Exceptional, (15)
"We had a great time at this adorable farmhouse! Our family of 5 enjoyed cooked meals together at the table, tea and coffee every morning, and board games every night! Tom was extremely hospitable and made sure our stay was perfect!"
Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains
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 Home Features Breathtaking Valley Views and Hot Tub
10.0 out of 10, Exceptional, (330)
"We had a great stay. The weather cooperated and we could use the 3 spacious patios to the fullest. The view is outstanding and the cabin is remote yet really close to amenities and shopping. Great times had by all."
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub
Beach
❤️ Secluded 1940s Romantic Tiny House on the River
10.0 out of 10, Exceptional, (41)
"The tiny house is exactly as described. Its small, clean, cozy and comfortable. The location right on the river is fantastic. Being able to have a fire right by the water each night was such a plus. In better weather would be a great put in for canoeing, kataking. Very close many historic sights, unique shops, and outdoor activities. The hosts are very thoughtful, kind and responsive. We will be staying again!!"
The price is €138
per night
19 May - 20 May
❤️ Secluded 1940s Romantic Tiny House on the River
Smart TV, DVD player, books, video library
Cozy Mountain Cabin w/ Steam Shower! Family Friendly!
10.0 out of 10, Exceptional, (26)
"We loved our one night stay at this cozy cabin, the steam shower was amazing. Definitely recommend!"
The price is €311
per night
20 May - 21 May
Cozy Mountain Cabin w/ Steam Shower! Family Friendly!
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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, (1306)
"Hhjjggjj"
The price is €112
per night
12 May - 13 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, (744)
"Clean and comfortable property. Staff was attentive. Breakfast was free and had a nice selection of items."
The price is €85
per night
7 May - 8 May
Microtel Inn & Suites by Wyndham Winchester
Seasonal outdoor pool
Travelodge by Wyndham Winchester
2.5 star property
8.0 out of 10, Very good, (1058)
"Very nice"
The price is €72
per night
6 May - 7 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 €133 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.

What are some of the best holiday rentals that Winchester has to offer?

Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI: This holiday home rental outside of Winchester is located on a river, and has a fireplace, a balcony and a BBQ 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 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Winchester?

Choose from 15 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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