Winchester Holiday Rentals

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Holiday Rentals in Winchester

Hidden Gem in the woods with hot tub

Berkeley Springs
9.6 out of 10, Exceptional, (84)
"Beautiful cabin. Updated photos are accurate but the space is even bigger in person. Hot tub and fire pit were great. House is clean and well equipped. Would stay again in a heartbeat. "
United States
Paul P.
Hidden Gem in the woods with hot tub

Private, light filled retreat space... with your own pickleball court!

Berkeley Springs
10.0 out of 10, Exceptional, (59)
"We loved this place! The view was beautiful. Enjoyed the pickleball court. Would highly recommend it to anyone looking for a relaxing getaway!"
United States
Denise H.
Private, light filled retreat space... with your own pickleball court!

Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

Harpers Ferry
10.0 out of 10, Exceptional, (79)
"Absolutely delightful!"
United States
John M.
The price is NZ$498
includes taxes & fees
10 Nov - 11 Nov
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

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

Berkeley Springs
9.8 out of 10, Exceptional, (289)
"It was a great time, easy check in and out! Grill and hot tub were great, and there was an amazing view of the stars."
United States
Julian B.
The price is NZ$544
includes taxes & fees
16 Nov - 17 Nov
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.

Dreamtime - Modern A-frame Cabin w/ Hot tub

Berkeley Springs
10.0 out of 10, Exceptional, (50)
"Awesome place! Perfect for 4 people. Great long weekend!"
United States
Stephanie P.
Dreamtime - Modern A-frame Cabin w/ Hot tub

Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray

2.0 star property
Luray
10.0 out of 10, Exceptional, (40)
"Wonderful vacation home in a great location. We visited Shenandoah NP and Luray Caverns both just 10-15 min away. Clean spacious and well equipped home. Would definitely stay here again. "
United States
Amy M.
The price is NZ$674
includes taxes & fees
11 Nov - 12 Nov
Amazing Grace log cabin home with 3 bedrooms, WiFi and AC in breathtaking Luray

Cabin w New Hot Tub, River/Kayak, WiFi, & Fire Pit

Great Cacapon
9.4 out of 10, Exceptional, (192)
"Overall a decent cabin. Think it’s probably best if you have a group or family of 6 looking for something economical. Seems like the cabin could use an overall refresh. Wish the hot tub was on the enclosed patio. "
United States
Brian
Cabin w New Hot Tub, River/Kayak, WiFi, & Fire Pit

A Cozy Bear Cottage! Quiet Mountain Cabin!

Luray
10.0 out of 10, Exceptional, (75)
"Great experience at the Cozy Bear Cottage. The cabin was just as described. Very comfortable and great communication from the host. "
United States
Jessica B.
A Cozy Bear Cottage! Quiet Mountain Cabin!

Canal Cabins

3.0 star property
Paw Paw
9.8 out of 10, Exceptional, (12)
"Great place for bikers to stay"
United States
mark
The price is NZ$229
includes taxes & fees
10 Nov - 11 Nov
Canal Cabins

"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

Rileyville
10.0 out of 10, Exceptional, (344)
"We had a great time at "Walden!" Beautiful location...Everything as advertised and more!! Plan to return...Highly recommend!! "
United States
Stephen D.
The price is NZ$487
includes taxes & fees
13 Nov - 14 Nov
"Walden" Modern Cabin on 54 Riverfront Acres along Shenandoah River w/Hot Tub

Outdoor Theatre | Hot Tub | Fire Pit | Dogs

Luray
9.8 out of 10, Exceptional, (56)
"Just as described online. Beautiful and secluded with great amenities. We really enjoyed our time there."
United States
Cheryl O.
The price is NZ$543
includes taxes & fees
12 Nov - 13 Nov
Outdoor Theatre | Hot Tub | Fire Pit | Dogs

Beautiful Private Cabin, adjacent to the National Forest

Luray
9.8 out of 10, Exceptional, (136)
"Everything we hoped for in a weekend trip! The house smelled like cedar, was clean and very ample space. The hot tub was easy to operate; kitchen appliances helped cut down on eating out costs - would highly recommend and plan on making a reservation again!"
United States
Brieona C.
Beautiful Private Cabin, adjacent to the National Forest

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

Luray
9.8 out of 10, Exceptional, (80)
"We had a great experience for a family wedding! The place was very clean and was in a great local spot that was easy to get to our wedding venue. "
United States
Rebecca W.
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

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

Front Royal
9.6 out of 10, Exceptional, (332)
"Been staying here for years. Great spot"
United States
Nicholas D.
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo

Falling Leaf Cabin - Rustic Charm With Modern Decor!

Rileyville
9.8 out of 10, Exceptional, (302)
"Fallong Lead cabin is just the perfect little cabin. Everything you need to relax and unwind with gorgeous views and a wonderful hot tub. Looking forward to staying here again!!"
United States
Melissa R.
Falling Leaf Cabin - Rustic Charm With Modern Decor!

Private Log Cabin - Hot Tub, NEW SatelliteWi-Fi, Fireplace, Sm Pet Considered

Berkeley Springs
9.8 out of 10, Exceptional, (127)
"Everything was perfect Definitely recommended I liked that every room was climate controlled Very convenient "
United States
Donald C.
Private Log Cabin - Hot Tub, NEW SatelliteWi-Fi, Fireplace, Sm Pet Considered

Roadhaven 1830

3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (38)
"This cottage was super clean and cozy!!! The back yard was so relaxing with many games to keep adults and young kids entertained . I would highly recommend this place. I would live to stay again. The owner was very sweet also ❤️"
United States
Shirley
The price is NZ$270
includes taxes & fees
12 Nov - 13 Nov
Roadhaven 1830

Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks

Luray
10.0 out of 10, Exceptional, (13)
"Everything you need in this little space with easy access to deck with grill, fire pit and hot tub."
United States
Traci M.
The price is NZ$437
includes taxes & fees
12 Nov - 13 Nov
Cute Riverside Cabin w Hot Tub, Fire Pit, & Kayaks

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

Rileyville
10.0 out of 10, Exceptional, (336)
"Place was beautiful and lived up to the name Solitude. Spent our honeymoon in perfect bliss. Great location to get away. "
United States
Sumcountryguy
The price is NZ$517
includes taxes & fees
25 Nov - 26 Nov
"Solitude" Secluded 1 BR Cabin Nestled in the Woods w/ Hot Tub near Luray, VA.

Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4

Luray
10.0 out of 10, Exceptional, (62)
"Fantastic hosts; very responsive. Cute place. Shower is small, but really great. Quiet neighborhood. Would stay again. "
United States
Ashley L.
The price is NZ$440
includes taxes & fees
11 Nov - 12 Nov
Tiny Barn w/Modern Charm on 3 Acres, Mountain and Pasture Views- Sleeps 4
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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Top Winchester Hotel Reviews

Find out more about Winchester

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, 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 NZ$229 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 17 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 Bright Box Theater and Winchester Little Theater. Other places in town to visit include Patsy Cline Historic House and Museum of the Shenandoah Valley.

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.