Winchester Vacation Rentals

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Our top choices for Winchester vacation rentals

Terrace/patio

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.
$151 nightly
The price is $164
Jan 19 - Jan 20
Total with taxes and fees
Luxury tiny home farm stay on historic property with hot tub in Stephens City
Terrace/patio

"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, (4 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.
$367 nightly
The price is $405
Feb 2 - Feb 3
Total with taxes and fees
"Prima BnB" a Superb 4-bedroom cottage on the mountain near Front Royal
Outdoor spa tub

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)
"Fun location near tons of wineries, bowling, trails, and mountain living. Place is really nice with a grill, solo stove, kfantastic kitchen"
United States
Bret L.
$323 nightly
The price is $356
Jan 28 - Jan 29
Total with taxes and fees
A-Frame near Shenandoah National Park - Pet friendly, EV Charger, Hot Tub
Property grounds

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.
$385 nightly
The price is $425
Jan 22 - Jan 23
Total with taxes and fees
The Vue - Mountain Top hot tub overlooking the Shenandoah River
Terrace/patio

Mountain View Bungalow in Front Royal

Mountain View Bungalow in Front Royal
Front Royal
10.0 out of 10, Exceptional, (12 reviews)
"Property was just what we were looking for "
United States
Tim C.
$200 nightly
The price is $223
Jan 19 - Jan 20
Total with taxes and fees
Mountain View Bungalow in Front Royal
Interior

Rosamond nice downtown studio apt

Rosamond nice downtown studio apt
Winchester Historic District
8.0 out of 10, Very Good, (2 reviews)
"Small but appropriately priced."
United States
John M.
$170 nightly
The price is $193
Jan 29 - Jan 30
Total with taxes and fees
Rosamond nice downtown studio apt
Interior

Lamontagne Farmhouse a Rural Pristine Setting

Lamontagne Farmhouse a Rural Pristine Setting
Bluemont
10.0 out of 10, Exceptional, (12 reviews)
"We loved our stay at this beautiful tranquil farmhouse. Our two Golden’s enjoyed the outdoor space. Hiking close by, a beautiful drive to visit Middleburg is a must. We highly recommend this charming getaway."
United States
AnneMarie M.
$220 nightly
The price is $251
Jan 19 - Jan 20
Total with taxes and fees
Lamontagne Farmhouse a Rural Pristine Setting
Microwave, oven, stovetop, dishwasher

Shenandoah River Retreat: Pool Table and Fireplace

Shenandoah River Retreat: Pool Table and Fireplace
2.0 star property
Front Royal
$284 nightly
The price is $314
Jan 19 - Jan 20
Total with taxes and fees
Shenandoah River Retreat: Pool Table and Fireplace
Exterior

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
10.0 out of 10, Exceptional, (2 reviews)
"Had a good time during my stay and loved seeing Shenandoah"
United States
Kye Y.
$259 nightly
The price is $286
Jan 20 - Jan 21
Total with taxes and fees
Cozy A frame cabin in quaint Front Royal. Dog friendly
Interior

NEW! Historic Schoolhouse HotTub+FirePit+Wineries

NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Fauquier County
8.0 out of 10, Very Good, (1 review)
"The listing indicated pets were welcome and we were able to bring our 13 year old dog, who loves traveling with my husband and I. There was some initial confusion after we booked the Schoolhouse, saying pets are prohibited. Through contact with the host, it was cleared up pretty quickly. All in all, the place was comfortable and we had what we needed to cook a couple of meals. I loved the area and enjoyed walking our dog on the state-maintained back roads. We would have liked to take advantage...
United States
Kathy S.
$285 nightly
The price is $287
Jan 20 - Jan 21
Total with taxes and fees
NEW! Historic Schoolhouse HotTub+FirePit+Wineries
Property grounds

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.
$293 nightly
The price is $323
Jan 18 - Jan 19
Total with taxes and fees
Newly renovated Farm cottage with Mountain views
Property grounds

Apple Mountain Retreat

Apple Mountain Retreat
Linden
10.0 out of 10, Exceptional, (21 reviews)
"Great place to stayed "
United States
Mike F.
$212 nightly
The price is $234
Jan 17 - Jan 18
Total with taxes and fees
Apple Mountain Retreat
Property grounds

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
$206 nightly
The price is $227
Jan 19 - Jan 20
Total with taxes and fees
Blue Mountain Cabin, secluded, perfect for couples, near main road
Property grounds

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.
$237 nightly
The price is $270
Jan 19 - Jan 20
Total with taxes and fees
Lunar Loft, with mountain views
Terrace/patio

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.
$376 nightly
The price is $428
Jan 19 - Jan 20
Total with taxes and fees
Historic Bluemont Village Home
Smart TV, books

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall

Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
2.0 star property
Winchester Historic District
8.6 out of 10, Excellent, (4 reviews)
"Clean property. Convenient to Old Town Winchester. All and all good property. Needs new bedroom pillows. Best."
United States
matthew r.
$204 nightly
The price is $231
Jan 21 - Jan 22
Total with taxes and fees
Dreamweaver — 1BR 1BA just two blocks from the downtown walking mall
Smart TV

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.
$367 nightly
The price is $405
Jan 17 - Jan 18
Total with taxes and fees
Welcome to the Ladybug Retreat!
Exterior detail

The Stock Exchange downtown 3rd floor studio apt

The Stock Exchange downtown 3rd floor studio apt
2.0 star property
Winchester Historic District
6.0 out of 10, (1 review)
$175 nightly
The price is $198
Jan 29 - Jan 30
Total with taxes and fees
The Stock Exchange downtown 3rd floor studio apt
Exterior

Bluemont home just minutes to wineries, breweries, hiking and more!

Bluemont home just minutes to wineries, breweries, hiking and more!
Bluemont
$377 nightly
The price is $419
Jan 20 - Jan 21
Total with taxes and fees
Bluemont home just minutes to wineries, breweries, hiking and more!
Exterior

Big Sunny Family House

Big Sunny Family House
Front Royal
10.0 out of 10, Exceptional, (42 reviews)
"Wonderful house and town! Loved every minute of our trip! "
United States
MaryAnn G.
$357 nightly
The price is $397
Jan 27 - Jan 28
Total with taxes and fees
Big Sunny Family House
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

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent
"This is our number one spot to stay in in Winchester. The location is perfect. Rooms are clean and modern."
Billy 2-night trip
Posted 3 days ago
Microtel Inn & Suites by Wyndham Winchester

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $225 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we offer vacation rentals in Winchester near Shenandoah Valley Discovery Museum, or you can go with a secluded option if you want a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theater scene while you're visiting.

What are some of the best vacation home rentals in Winchester?

Charming mountaintop cabin with hot tub, pool table, and breathtaking views: This vacation home rental near Winchester is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with an arcade game room and a hot tub.

How many vacation rentals will I find in Winchester?

Choose from 15 Expedia vacation rentals in Winchester for a memorable vacation.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Nalls Farm Market are a couple of family-friendly sights, whereas cultural attractions include Bright Box Theater and Museum of the Shenandoah Valley. Other places in town to visit include Apple Blossom Mall and Rock Harbor Golf Course.

What’s a vacation rental in Winchester like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Winchester. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for family trips.