A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Winchester Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Winchester vacation rentals

A wooden cabin with a garage, surrounded by trees and a gravel driveway.

1. The Pond Cabin

The Pond Cabin
2.0 star property
Linden
$414 nightly
The price is $457
Sep 29 - Sep 30
Total with taxes and fees
The Pond Cabin
A two-story residential building with a front porch, a pathway leading to the entrance, and a well-maintained lawn.

2. Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (51 reviews)
"Wow what an awesome place to stay!! Clean and so nice. I highly recommend."
United States
Mickey
$132 nightly
The price is $149
Oct 12 - Oct 13
Total with taxes and fees
Roadhaven1830
A modern living room with a fireplace, a large sofa, a coffee table, and a TV mounted on the wall.

3. Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!

Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!
3.0 star property
Luray
$290 nightly
The price is $334
Sep 20 - Sep 21
Total with taxes and fees
Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!
A hallway with wooden flooring, a ceiling fan, and a door leading to a room with a bed.

4. Schilling House

Schilling House
3.0 star property
Bolivar
$321 nightly
The price is $343
Sep 20 - Sep 21
Total with taxes and fees
Schilling House
A cozy living room with a fireplace, a dining area with a table and chairs, and a large window overlooking a forest.

5. 2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
6.4 out of 10, (12 reviews)
"This place was wonderful. When have stayed at 4 different cabins like this and this was our favorite. The place was cozy and clean. The pantry was well stocked. The fire pit even had a wood fire prepared. The owners were really nice and communicated well. The facilities at the woods were included We live very the location and the hot tub Highly recommend"
United States
Christopher
$269 nightly
The price is $279
Sep 22 - Sep 23
Total with taxes and fees
2-Bedroom cabin Hot tub Fireplace PS5
A bed with a dark quilted cover, two beige pillows, and a headboard with two wall-mounted lamps.

6. Canal Cabins

Canal Cabins
3.0 star property
Paw Paw
9.8 out of 10, Exceptional, (17 reviews)
"A great place for a nice getaway. The place is well tailored for the cyclists."
United States
Nebojsa
$131 nightly
The price is $148
Oct 17 - Oct 18
Total with taxes and fees
Canal Cabins
A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and two stools.

7. 'thomson Farm' Classic Home < 10 Mi to Vineyards!

'thomson Farm' Classic Home < 10 Mi to Vineyards!
3.0 star property
Leesburg
$1,876 nightly
The price is $2,139
Sep 20 - Sep 21
Total with taxes and fees
'thomson Farm' Classic Home < 10 Mi to Vineyards!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Quality Inn Winchester

Quality Inn Winchester

10/10 Excellent
"The hotel is conveniently located, clean, pleasant and very reasonably priced. It was just what we needed for an overnight stop with a dog."
Neiri 1-night trip
Posted 7 hours ago
Quality Inn 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 $148 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?

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails: This vacation home near Winchester is located in a rural location and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Rocking S Ranch 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 Patsy Cline Historic House and Apple Blossom Mall.

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.