Winchester Holiday Rentals

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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
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 HK$781
HK$2,469 total
includes taxes & fees
28 May - 29 May
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Garden
Family Farmhouse Inn
3.0 star property
9.6 out of 10, Exceptional, (27)
"Nice room and outdoor space. Nearby highway noise detracted from outside atmosphere. Bed was very comfortable, pleasant accommodations . It would be nice to have a breakfast included as there are no nearby places to eat."
The price is HK$953
HK$1,071 total
includes taxes & fees
8 Jun - 9 Jun
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 HK$922
HK$2,280 total
includes taxes & fees
29 May - 30 May
Cabin w Hot Tub, Indoor Pool / Gym Access, & Grill
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
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
2 bedrooms, WiFi, bed sheets
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
9.4 out of 10, Exceptional, (299)
"Great view."
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River
Smart TV, DVD player, books, video library
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
10.0 out of 10, Exceptional, (28)
"This little cabin was great!! Comfortable beds. Very clean. Brigid the host was so responsive. Instructions were very clear. She even answered our questions about recommendations for a goos hiking trail! Highly recommend! I hope we will be back."
The price is HK$1,133
HK$2,573 total
includes taxes & fees
28 May - 29 May
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
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
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
Property grounds
Cozy Lakeside Homestead
10.0 out of 10, Exceptional, (165)
"Cabin was in great place within walking distance to lake,Paula the host very easy to get a hold of,property very clean"
The price is HK$1,641
HK$2,321 total
includes taxes & fees
4 Jun - 5 Jun
Cozy Lakeside Homestead
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 HK$586
HK$1,128 total
includes taxes & fees
9 Jun - 10 Jun
❤️ Secluded 1940s Romantic Tiny House on the 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 HK$1,836
HK$2,810 total
includes taxes & fees
7 Jun - 8 Jun
"Solitude" Secluded 1 BR Cabin w/ Hot Tub near Luray, VA.
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 HK$1,339
HK$3,157 total
includes taxes & fees
10 Jun - 11 Jun
Escape to Shenandoah River, Hot Tub after a Hike!
Secluded, Cozy Cottage in the Shenandoah Valley
10.0 out of 10, Exceptional, (144)
"Stayed here for a weekend for a mini honeymoon/wife’s birthday. The cabin had everything we needed and more. We stay at a lot of cabins around shenendoah valley and this one was definitely high on the list of quality. Very clean and cozy. We took a hike, enjoyed the fire pit and hot tub, grilled, and relaxed on the upper deck. All the appliances worked and shower was great. Our only issue was the bed was very noisy and sounded like it could use some attention or an upgrade, there was a good...
Secluded, Cozy Cottage in the Shenandoah Valley
Property grounds
Hidden Gem in the woods with hot tub
9.6 out of 10, Exceptional, (50)
"We had a great time. Cabin was clean, spacious and well maintained. The fire pit and hot tub were what we looked forward to the most... We were not disappointed."
Hidden Gem in the woods with hot tub
Property grounds
Riverside cottage, minutes from historic Harpers Ferry; private river access!
9.8 out of 10, Exceptional, (56)
"Not much to say other than it was a great stay. Scott was super responsive for the few questions we had and everything was clean and comfortable."
The price is HK$1,133
HK$1,730 total
includes taxes & fees
2 Jun - 3 Jun
Riverside cottage, minutes from historic Harpers Ferry; private river access!
Exterior
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
Cottage w Hot Tub, Pond & Kayaks, Fire Pit, & WiFi
8.8 out of 10, Excellent, (12)
"My partner and I booked this place for a little birthday getaway with our dog. We wanted somewhere with access to cute little towns and hiking, but that also provided us that West Virginia woodsy privacy, and this spot was perfect! Countless awesome hiking spots within 30 minutes. We day tripped to Frederick, MD one day (a little over an hour) and fell in love with the town. Berkeley Springs is an adorable town (though many tons are shot down this time of year so it was a little hard to plan...
The price is HK$820
HK$2,091 total
includes taxes & fees
28 May - 29 May
Cottage w Hot Tub, Pond & Kayaks, Fire Pit, & WiFi
Lake
Above The Rivers Edge Cabin #1
9.8 out of 10, Exceptional, (152)
"Had a fantabulos time! The cabin had everything we needed."
Above The Rivers Edge Cabin #1
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, (1351)
"Great front desk staff. Very friendly and professional Room was clean and perfect for our needs "
The price is HK$907
HK$987 total
includes taxes & fees
2 Jun - 3 Jun
La Quinta Inn & Suites by Wyndham Winchester
Lobby
Microtel Inn & Suites by Wyndham Winchester
2.5 star property
9.0 out of 10, Wonderful, (783)
"Friendly staff. Water pressure in shower could be a better. A little more attention to cleaning the bathrooms. "
The price is HK$658
HK$715 total
includes taxes & fees
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, (1068)
"Norhong real special"
The price is HK$549
HK$597 total
includes taxes & fees
9 Jun - 10 Jun
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.

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

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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.

Recent reviews of Winchester properties
Expedia verified reviews

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

5/5 Excellent
Pleasantly surprised
"Great front desk staff. Very friendly and professional Room was clean and perfect for our needs "
A verified traveller stayed at La Quinta Inn & Suites by Wyndham Winchester
Posted 9 hours ago
La Quinta Inn & Suites by Wyndham Winchester