Holiday Rentals in Winchester

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Our top choices for Winchester holiday rentals

Luxury tiny home farm stay on historic property with hot tub in Stephens City

Luxury tiny home farm stay on historic property with hot tub in Stephens City
2.0 star property
Stephens City
10.0 out of 10, Exceptional, (1 review)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
The price is €158
includes taxes & fees
10 Feb - 11 Feb
Luxury tiny home farm stay on historic property with hot tub in Stephens City

The Haven at Turkey Run • Hot Tub, Fire Pit, Games

The Haven at Turkey Run • Hot Tub, Fire Pit, Games
Strasburg
10.0 out of 10, Exceptional, (11 reviews)
"Loved the creek and the hot tub!!! Cant say enough good things about this place"
United States
Maxx H.
The price is €486
includes taxes & fees
11 Jan - 12 Jan
The Haven at Turkey Run • Hot Tub, Fire Pit, Games

The Royal Cabin | Private Getaway w/ Hot Tub

The Royal Cabin | Private Getaway w/ Hot Tub
Front Royal
9.8 out of 10, Exceptional, (11 reviews)
"House was very clean and well stocked. Great outdoor games for all ages. Perfect for our family and friends as we celebrated a wedding."
United States
mollie g.
The Royal Cabin | Private Getaway w/ Hot Tub

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown
Old Town Winchester
10.0 out of 10, Exceptional, (1 review)
"Beautiful space; helpful host."
United States
Sally C.
The price is €365
includes taxes & fees
23 Jan - 24 Jan
Magnolia Wind elegant 3 BR 1BA loft apartment park for free and walk downtown

Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA

Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA
Linden
10.0 out of 10, Exceptional, (3 reviews)
"Megan was exceptional at communications, the property was perfect for our Family Thanksgiving. "
United States
Lynne S.
The price is €477
includes taxes & fees
23 Jan - 24 Jan
Cozy Luxury, Meet Not Your Typical Cuties Cabin, a Secluded Retreat in Linden VA

Cozy A frame cabin in quaint Front Royal. Dog friendly

Cozy A frame cabin in quaint Front Royal. Dog friendly
2.0 star property
Front Royal
The price is €227
includes taxes & fees
12 Jan - 13 Jan
Cozy A frame cabin in quaint Front Royal. Dog friendly

The Vue - Mountain Top hot tub overlooking the Shenandoah River

The Vue - Mountain Top hot tub overlooking the Shenandoah River
2.0 star property
Front Royal
9.8 out of 10, Exceptional, (10 reviews)
"Our family had a lovely time at The Vue! It was clean, comfortable, and had everything we needed for a quick getaway. The mountain view was truly incredible and we enjoyed watching the sunrise with our coffee on the back deck. While there's not much of a yard, our pup enjoyed the outdoor space too! Thank for being a part of our family's special memories. We'll be back!"
United States
Alyssa L.
The price is €393
includes taxes & fees
21 Jan - 22 Jan
The Vue - Mountain Top hot tub overlooking the Shenandoah River

Welcome to the Ladybug Retreat!

Welcome to the Ladybug Retreat!
Boyce
10.0 out of 10, Exceptional, (1 review)
"This home is lovely and the host has thought of everything. We will definitely stay here again. "
United States
Catherine A.
The price is €356
includes taxes & fees
23 Jan - 24 Jan
Welcome to the Ladybug Retreat!

Cozy Bear Cabin | Hot Tub, Fenced Yard, Game & Theatre Rooms + THREE KING BEDS!

Cozy Bear Cabin | Hot Tub, Fenced Yard, Game & Theatre Rooms + THREE KING BEDS!
Front Royal
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful time staying there during our time at upperville. The quiet nights in the hot tub were just what we needed! Matthew was a wonderful host and so helpful ! We hope to come back again "
United States
grace g.
The price is €597
includes taxes & fees
22 Jan - 23 Jan
Cozy Bear Cabin | Hot Tub, Fenced Yard, Game & Theatre Rooms + THREE KING BEDS!

"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal

"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal
Front Royal
10.0 out of 10, Exceptional, (3 reviews)
"My family and I had a wonderful stay! The property and surrounding views are beautiful. The house was very clean and the host was very responsive when I had a question or two to ask. I highly recommend staying here!"
United States
Jay L.
The price is €383
includes taxes & fees
22 Jan - 23 Jan
"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal

Luxury Riverfront Home Getaway with Hot Tub

Luxury Riverfront Home Getaway with Hot Tub
2.0 star property
Warren County
Luxury Riverfront Home Getaway with Hot Tub

Blue Mountain Cabin, secluded, perfect for couples, near main road

Blue Mountain Cabin, secluded, perfect for couples, near main road
Front Royal
10.0 out of 10, Exceptional, (27 reviews)
"Great place to relax"
United States
Judy
The price is €199
includes taxes & fees
11 Jan - 12 Jan
Blue Mountain Cabin, secluded, perfect for couples, near main road

The Far View Retreat | Hot Tub + Scenic Views

The Far View Retreat | Hot Tub + Scenic Views
Front Royal
10.0 out of 10, Exceptional, (15 reviews)
"The cabin was spacious and well equipped. The rooms were clean and comfy. The hot tub was clean and refreshing after a long hiking day. Lovd the covered deck for watching sunrises and the deer. I heard a coyote howl early one morning."
United States
Gina H.
The price is €497
includes taxes & fees
19 Jan - 20 Jan
The Far View Retreat | Hot Tub + Scenic Views

Cameron Charmer pristine downtown apt with double master suites

Cameron Charmer pristine downtown apt with double master suites
Winchester
9.4 out of 10, Exceptional, (6 reviews)
"The home was exactly as advertised! It was also located in a great spot whichbwas within walking distance to many of the Historic District of Downtown Winchester. We will definitely be staying here again!"
United States
David K.
Cameron Charmer pristine downtown apt with double master suites

The Foxwood Cabin | Hot Tub, Screened Porch, Grill

The Foxwood Cabin | Hot Tub, Screened Porch, Grill
Front Royal
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful, quiet place to stay. Beds are very comfortable. Every room was very clean. "
United States
Alex H.
The price is €486
includes taxes & fees
11 Jan - 12 Jan
The Foxwood Cabin | Hot Tub, Screened Porch, Grill

3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!

3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!
Stephens City
9.4 out of 10, Exceptional, (8 reviews)
"Had a great stay at this property for a girls weekend. Nearby to cute shops, a nice winery, grocery stores and restaurants. Nice amenities with games, entertainment systems, outdoor space, and in a great neighborhood too. Lots of space for families or friend reunions. Will rent again here when staying in the area. "
United States
Maureen W.
3BDR, 3 Full-Bath house in City, 2 living rooms [3,000 sq. ft.] - Pet Friendly!

Delicious Cabin • Wine Country Retreat w/ Hot Tub

Delicious Cabin • Wine Country Retreat w/ Hot Tub
Linden
9.8 out of 10, Exceptional, (10 reviews)
"The cabin was impressive both inside and out. We loved the location and proximity to skyline drive. We would definitely stay here again as it made our trip so much more enjoyable. "
United States
Bill A.
The price is €485
includes taxes & fees
19 Jan - 20 Jan
Delicious Cabin • Wine Country Retreat w/ Hot Tub

Wilderness Ridge | Private Cabin w/ Mountain Views

Wilderness Ridge | Private Cabin w/ Mountain Views
Linden
9.4 out of 10, Exceptional, (6 reviews)
"great get away for a family retreat!!!"
United States
Rex P.
The price is €573
includes taxes & fees
12 Jan - 13 Jan
Wilderness Ridge | Private Cabin w/ Mountain Views

Historic Bluemont Village Home

Historic Bluemont Village Home
Bluemont
10.0 out of 10, Exceptional, (39 reviews)
"This was one of the best VRBO experiences I’ve had! Communication with the host was exceptional, and the home itself was gorgeous. It’s clear they have put a lot of thought into make this house a perfect getaway — it is beautifully decorated and has all the comforts of home. We will definitely stay here again!"
United States
Mary S.
The price is €376
includes taxes & fees
12 Jan - 13 Jan
Historic Bluemont Village Home

Newly renovated Farm cottage with Mountain views

Newly renovated Farm cottage with Mountain views
Strasburg
10.0 out of 10, Exceptional, (38 reviews)
"Beautiful place; very friendly hosts. We enjoyed our stay very much! We will visit again! "
United States
Shannon H.
The price is €285
includes taxes & fees
12 Jan - 13 Jan
Newly renovated Farm cottage with Mountain views
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, 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 €94 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?

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub: 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. It has 3 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 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 Bright Box Theater and Museum of the Shenandoah Valley. 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.