Winchester Holiday Rentals

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Holiday Rentals in Winchester

Dreamtime - Modern A-frame Cabin w/ Hot tub

10.0 out of 10, Exceptional, (34)
"The cabin was in a beautiful community and setting with a fabulous outdoor area facing the woods. Many amenities in the home that made our stay easy with nicely renovated interior. Owner was very willing and able to offer help with anything and was receptive to feedback. Thank you!"
The price is AU$592
includes taxes & fees
3 Dec - 4 Dec
Dreamtime - Modern A-frame Cabin w/ Hot tub

Secluded Pet-Friendly High-Tech Log Cabin in the Woods

9.6 out of 10, Exceptional, (165)
"I enjoyed every peaceful moment I was there! Living near, and working in a big city is loud and stressful. This was just what the Dr. ordered! Beautiful home in a beautiful setting with great amenities. Loved the lower level deck and propane fire pit that was ready to use! My older dog had a few problems traversing the steps but he loved being there as well!!! Already booked another stay! "
Secluded Pet-Friendly High-Tech Log Cabin in the Woods

Hidden Gem in the woods with hot tub

9.4 out of 10, Exceptional, (63)
"Great location, a little out of the way, but very relaxing. Great hot tub and fire pit. My family and I had an amazing time. "
Hidden Gem in the woods with hot tub

Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

9.6 out of 10, Exceptional, (289)
"We had a wonderful time in this cabin. It is very peaceful and quiet. The view is amazing and we loved watching all the wildlife. Perfect location to front royal and many wineries but staying in and enjoying the beautiful cabin and scenery was our favorite ! "
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

9.8 out of 10, Exceptional, (169)
"this was a great first experience. The cabin was fantastic and the kitchen was exceptional. The downstairs was well stocked with different games and I really enjoyed all the different trails that nested up against this great cabin."
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

10.0 out of 10, Exceptional, (299)
"Beautiful!! So very peaceful. We will go back 💯 "
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.8 out of 10, Exceptional, (86)
"We were looking to unplug for a night, and this cottage was the perfect spot! Clean and well kept, calm and quiet surroundings. One note is that the WiFi was not working. We didn’t need it for our trip, but something to keep in mind!"
The price is AU$341
includes taxes & fees
25 Nov - 26 Nov
Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Charming mountaintop cabin with hot tub, pool table, and breathtaking views

9.8 out of 10, Exceptional, (187)
"Enjoyed our stay. Very quiet as the summer season was over. Rained most of the time we were there as remnants of hurricane Helena passed thru. We spent a lot of time just relaxing, hot tubbing between rain drops and hanging out on the covered deck (our favorite spot). Pool table room very nice. Huge bathroom downstairs. Area was nice with town close by, just down the very windy road. No complaints, would recommend to friends."
Charming mountaintop cabin with hot tub, pool table, and breathtaking views

Star view cabin-Riverfront

9.8 out of 10, Exceptional, (297)
"Great stay. Incredible views. Perfect weekend getaway. If you want to have a nice dinner bring your own glassware. Supplies were minimal in the house. "
Star view cabin-Riverfront

Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

9.8 out of 10, Exceptional, (260)
"The cabin was extremely clean, had anything you would need for the weekend. Owners responded very fast when we had any questions. Location is beautiful, and hot tube was perfect. Our only issue was the sulfur smell inside the cabin when we ran the water or took a shower. We did contact the owner and she did explain that it may of been due to the rain, She told us what to do and it seemed to help for - day, but next day smell was back. We didn’t want to keep bothering her about it, because we...
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Romantic, rustic, private A-frame chalet tucked in the woods - 4 miles to town!

8.6 out of 10, Excellent, (34)
"Will visit again!"
Romantic, rustic, private A-frame chalet tucked in the woods - 4 miles to town!

Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

10.0 out of 10, Exceptional, (358)
"We had a wonderful stay at Deer Haven. The house was clean and very comfortable. The views were amazing, and the hot tub was perfect after long days of hiking. Nice outside deck seating and interior seats to allow for maximum views enjoyment! Would definitely rent this house again if we return to the area."
Secluded Mountain Home Features Breathtaking Valley Views and Hot Tub

Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

9.6 out of 10, Exceptional, (327)
"Amazing!!!"
Authentic Mountain Log Cabin Perched On A Cliff Side Above The Shenandoah River

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (47)
"My husband and I stayed here to celebrate our second anniversary. We wanted just a quiet getaway and it was the perfect place. Definitely will have to come back again."
The price is AU$172
includes taxes & fees
3 Dec - 4 Dec
❤️ Secluded 1940s Romantic Tiny House on the River

Cottage w Hot Tub, Pond & Kayaks, Fire Pit, & WiFi

9.0 out of 10, Wonderful, (27)
"Always have a Wonderful stay at Tony’s properties!"
The price is AU$386
includes taxes & fees
1 Dec - 2 Dec
Cottage w Hot Tub, Pond & Kayaks, Fire Pit, & WiFi

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

9.8 out of 10, Exceptional, (204)
"This is three fifth time we’ve stayed here. It’s a gorgeous secluded area, so quiet and peaceful with no one around. Walk out the front door for hours on end of hiking. Great beds, great tv, fun pool table and three best porch! Will continue to return! Pet friendly too!"
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

Beautiful 360 views!

10.0 out of 10, Exceptional, (172)
"This is our third stay at this cottage. We wouldn't stay anywhere else."
Beautiful 360 views!

Cozy Lakeside Homestead

10.0 out of 10, Exceptional, (177)
"Lots of great space indoors and outdoors for a variety of activities. "
The price is AU$462
includes taxes & fees
2 Dec - 3 Dec
Cozy Lakeside Homestead

Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!

10.0 out of 10, Exceptional, (76)
"Whisky Hill is an amazing cabin. My husband and I enjoyed our stay. Everything was clean, and had everything we needed. It was not difficult at all to find. We thoroughly enjoyed our time and can’t wait to be back. It was a great find!! Highly recommend if coming to the Linden area. "
Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!

Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!

9.8 out of 10, Exceptional, (19)
"My friends and I always choose a new cabin for our annual fall getaway. We've not had a bad experience yet. Mountain Mama's Woodpecker Woods did not disappoint, either! Comfortable, warm, clean, spacious log cabin. It had everything we needed. In fact, it was so relaxing, we never made it to the hot tub. We did visit Harper's Ferry Park and enjoyed walking the hiking trail to the downtown area. :-) We especially loved the close proximity to the Washington, DC Metro area. If there was anything...
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!
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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Other types of properties in Winchester you may be interested in

La Quinta Inn & Suites by Wyndham Winchester

2.5 star property
9.2 out of 10, Wonderful, (1727)
"Clean and safe feeling. Excellence workers, prompt, courteous and knowledgeable. "
The price is AU$178
includes taxes & fees
1 Dec - 2 Dec
La Quinta Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 star property
9.0 out of 10, Wonderful, (1049)
"Confortable bed to sleep in, noisy bathroom fan."
The price is AU$127
includes taxes & fees
1 Dec - 2 Dec
Microtel Inn & Suites by Wyndham Winchester

Red Roof Inn Winchester, VA

2.0 star property
7.4 out of 10, Good, (1039)
"As described "
The price is AU$101
includes taxes & fees
5 Dec - 6 Dec
Red Roof Inn Winchester, VA
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Breathtaking views with an indoor private pool, come escape with us: This holiday home rental outside of Winchester is located in the mountains, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Winchester?

Choose from 21 Expedia holiday rentals in Winchester for a memorable holiday.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Rocking S Ranch 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 Patsy Cline Historic House 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.