Winchester Holiday Rentals

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Our top choices for Winchester holiday rentals

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, (31 reviews)
"Very cozy cabin for two, great for a secluded getaway within range of great places to visit. Had everything we needed."
United States
Tom C.
The price is NZ$404
includes taxes & fees
29 Mar - 30 Mar
Blue Mountain Cabin, secluded, perfect for couples, near main road

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Linden
9.4 out of 10, Exceptional, (13 reviews)
"Great place to stay to catch the northern entrance to Shenandoah. Comfortable beds, great furniture, and easy drive to Front Royal for dining. "
United States
Scott M.
The price is NZ$635
includes taxes & fees
14 Apr - 15 Apr
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub

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
Stephens City
10.0 out of 10, Exceptional, (2 reviews)
"Fresh bread, farm eggs, an amazing host! What a perfect place to stay. "
United States
Chris F.
The price is NZ$280
includes taxes & fees
8 Apr - 9 Apr
Luxury tiny home farm stay on historic property with hot tub in Stephens City

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (17 reviews)
"We enjoyed our stayed so much! This location is perfect. This property is so clean. "
United States
Nicole Z.
The price is NZ$376
includes taxes & fees
29 Mar - 30 Mar
Mountain View Bungalow in Front Royal

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 NZ$544
includes taxes & fees
29 Mar - 30 Mar
Newly renovated Farm cottage with Mountain views

Hidden Gem on Hidden Valley Lane

Hidden Gem on Hidden Valley Lane
Linden
9.6 out of 10, Exceptional, (27 reviews)
"Great place. Very clean, lots of comfortable rooms. Nice outside area for dogs. "
United States
Lisa W.
The price is NZ$766
includes taxes & fees
29 Mar - 30 Mar
Hidden Gem on Hidden Valley Lane

Dog-Friendly Cottage w Playground, Grill & Games

Dog-Friendly Cottage w Playground, Grill & Games
Middletown
9.6 out of 10, Exceptional, (17 reviews)
"Clean cute house, exactly as described. Close to Shenandoah national park and skyline drive. Hosts very communicative "
United States
Corrin D.
Dog-Friendly Cottage w Playground, Grill & Games

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View
Front Royal
9.6 out of 10, Exceptional, (17 reviews)
"Nice place, comfortable bed. Close to hiking in the area."
United States
Jake M.
The price is NZ$375
includes taxes & fees
6 Apr - 7 Apr
Country cottage beside stocked pond on 40 acres and Blue ridge Mountain View

Lunar Loft, with mountain views

Lunar Loft, with mountain views
Bluemont
8.8 out of 10, Excellent, (6 reviews)
"Stayed here with my 5 month old daughter, my mom and a friend and we had a blast. Kind folks, beautiful grounds and a super cute barn apartment! The fresh flowers in the kitchen were a lovely touch. "
United States
Haley M.
The price is NZ$461
includes taxes & fees
30 Mar - 31 Mar
Lunar Loft, with mountain views

The Pond Cabin: Hot Tub & Stocked Pond

The Pond Cabin: Hot Tub & Stocked Pond
Linden
10.0 out of 10, Exceptional, (34 reviews)
"It was the perfect home away from home in a place that allowed our little family to take a breath of nature and just be. Close enough to many fun adventures. The amenities provided on the property also kept us very busy!"
United States
Brena H.
The price is NZ$878
includes taxes & fees
29 Mar - 30 Mar
The Pond Cabin: Hot Tub & Stocked Pond

The Juniper Cabin • Cozy Hideaway w/ Hot Tub

The Juniper Cabin • Cozy Hideaway w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (22 reviews)
"We had a fantastic time staying at this property for the weekend."
United States
Colin N.
The price is NZ$663
includes taxes & fees
19 Apr - 20 Apr
The Juniper Cabin • Cozy Hideaway w/ Hot Tub

Mountain Cabin • Views • Hot Tub • 5 Beds • Skyline Drive

Mountain Cabin • Views • Hot Tub • 5 Beds • Skyline Drive
Front Royal
10.0 out of 10, Exceptional, (5 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 NZ$682
includes taxes & fees
8 Apr - 9 Apr
Mountain Cabin • Views • Hot Tub • 5 Beds • Skyline Drive

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Front Royal
9.2 out of 10, Wonderful, (5 reviews)
"Absolutely perfect spot for a leaf-peeping getaway. Clean, charming, romantic! Close to antiques, vineyards and Shenandoah!"
United States
Paul B.
The price is NZ$756
includes taxes & fees
13 Apr - 14 Apr
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub

Nostalgia Lane in the heart of the city

Nostalgia Lane in the heart of the city
Old Town Winchester
9.0 out of 10, Wonderful, (15 reviews)
"Adorable place and perfect for Winchester and surrounding parks, wineries, and farms."
United States
Tracy F.
The price is NZ$562
includes taxes & fees
1 Apr - 2 Apr
Nostalgia Lane in the heart of the city

Mountain cabin near national park & wineries

Mountain cabin near national park & wineries
Linden
10.0 out of 10, Exceptional, (29 reviews)
"The house and location were perfect for a little getaway with friends. It was very clean, and the location was great! We were very pleased with the entire experience."
United States
Jennifer d.
The price is NZ$718
includes taxes & fees
29 Mar - 30 Mar
Mountain cabin near national park & wineries

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 NZ$834
includes taxes & fees
14 Apr - 15 Apr
The Foxwood Cabin | Hot Tub, Screened Porch, Grill

Shenandoah mountain cottage w/hot tub & fire pit

Shenandoah mountain cottage w/hot tub & fire pit
Front Royal
9.0 out of 10, Wonderful, (31 reviews)
"The house itself was clean, the beds are comfortable, and it is in a nice, quiet, and private location. The property manager was very pleasant and responsed to any questions or concerns quickly. "
United States
Elissa S.
The price is NZ$534
includes taxes & fees
30 Mar - 31 Mar
Shenandoah mountain cottage w/hot tub & fire pit

Skyland Hideaway | Mountain Cabin w/ Hot Tub

Skyland Hideaway | Mountain Cabin w/ Hot Tub
Linden
10.0 out of 10, Exceptional, (15 reviews)
"Quiet with amenities to support R&R, enjoying nature, and togetherness."
United States
Patricia B.
The price is NZ$737
includes taxes & fees
6 Apr - 7 Apr
Skyland Hideaway | Mountain Cabin w/ Hot Tub

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Bluemont
10.0 out of 10, Exceptional, (7 reviews)
"Had a fun visit. Property and host we're excellent."
United States
Daniel D.
The price is NZ$471
includes taxes & fees
31 Mar - 1 Apr
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Morocco Loft 2BR overlooking city walking mall

Morocco Loft 2BR overlooking city walking mall
Old Town Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great property with all the comforts of home"
United States
Kristen R.
The price is NZ$546
includes taxes & fees
31 Mar - 1 Apr
Morocco Loft 2BR overlooking city walking mall
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$587 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?

Secluded River Cabin Getaway (Masten Cabin): This holiday home rental outside of Winchester is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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 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.