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Winchester Vacation Rentals

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Vacation Rentals in Winchester

Cozy 2 bedroom apartment 2 miles from historic Winchester.
The price is $135 per night from Jun 30 to Jul 1
Stay at this apartment in Winchester. Enjoy free WiFi, onsite parking, and an in-room DVD player. Popular attractions Jim Barnett Park and Abram's Delight are ...
4.3/5 Excellent! (3 reviews)
Great Stay!
"Stayed a couple nights for a wedding in the area. Great place, plenty of room, no issues."

Reviewed on Jun 11, 2022

Cozy 2 bedroom apartment 2 miles from historic Winchester.
Experience Basil! Modern Gem in Historic District!
Stay at this vacation home in Winchester. Enjoy free WiFi, onsite parking, and a garden. Popular attractions Handley Regional Library and Stonewall Jackson's ...
5/5 Exceptional! (2 reviews)
Winchester weekend
"Perfect location for a Winchester visit. Clear communication with the hosts and an overall easy process."

Reviewed on Jun 25, 2022

Experience Basil! Modern Gem in Historic District!
APM Executive Suites
3 out of 5
2971 Valley Ave, Winchester, VA, 22601
Stay at this 3-star apartment in Winchester. Enjoy free WiFi, free parking, and a conference center. Popular attractions The Kernstown Battlefield and Apple ...
3.9/5 Good! (17 reviews)
A bait and switch. Not worth it
"On check in and check out, no masks. Kim did put one on. Said it was overbooked. Upgrade to corporate apt. By pics, i would have stayed with suite. Old apt. Big living room. 2 couches. 2 ceiling fan light and floor lamp. Kitchen was ok. No can opener. Bath was clean and bright. Bedroom was smallish. ..."

Reviewed on Jan 28, 2021

APM Executive Suites
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Yellow Submarine trendy basement apt w/courtyard
Stay at this apartment in Winchester. Enjoy free WiFi, a patio, and a Smart TV. Popular attractions Handley Regional Library and Old Court House Civil War Museum ...
Yellow Submarine trendy basement apt w/courtyard
Escape to Blossom, a EuroLux MidCentury Experience
Stay at this property in Winchester. Enjoy free WiFi, onsite parking, and a garden. Popular attractions Handley Regional Library and Stonewall Jackson's Headquarters ...
Escape to Blossom, a EuroLux MidCentury Experience
City Charmer near Historic OldTown Winchester.
Stay at this vacation home in Winchester. Enjoy free WiFi, onsite parking, and a garden. Our guests praise the convenient parking and the overall value in our ...
5/5 Exceptional! (44 reviews)
Beautiful home and close to downtown Winchester
"Great location. Quick walk or Uber drive to downtown Winchester. Perfect little getaway. Home is cute and very inviting."

Reviewed on May 27, 2022

City Charmer near Historic OldTown Winchester.
Modern Upscale Home, Historic Downtown Winchester
Stay at this vacation home in Winchester. Enjoy free WiFi, onsite parking, and a patio. Popular attractions Patsy Cline Historic House and Shenandoah Valley ...
5/5 Exceptional! (10 reviews)
Perfection
"The house was beautifully decorated and spotless. The host had so many extras for us...coffee, sweets, treats, kitchen supplies, toiletries and so on. She went above and beyond our expectations. Front porch was our favorite. Kitchen was stocked and soooooooo organized. We walked to town each day ..."

Reviewed on Jun 17, 2022

Modern Upscale Home, Historic Downtown Winchester
Colonial Getaway Near Old Town Historic Winchester
Stay at this vacation home in Winchester. Enjoy WiFi, onsite parking, and fenced yards. Popular attractions Jim Barnett Park and Abram's Delight are located ...
4.9/5 Exceptional! (30 reviews)
Amazing House!
"Awesome kitchen and space! Everything was great! :)"

Reviewed on Jun 2, 2022

Colonial Getaway Near Old Town Historic Winchester
Lofts for weekly rentals! 2 miles from historic downtown.
Stay at this property in Winchester. Enjoy WiFi, a TV, and cable/satellite TV. Popular attractions The Kernstown Battlefield and Apple Blossom Mall are located ...
Lofts for weekly rentals! 2 miles from historic downtown.
Crystal Lake House
Winchester, VA
Stay at this vacation home in Winchester. Enjoy 1 bedroom. Discover genuine guest reviews for Crystal Lake House along with the latest prices and availability ...
Crystal Lake House
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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.

Other types of properties in Winchester you may be interested in

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA, 22602
Fully refundableReserve now, pay when you stay
The price is $63 per night from Jul 11 to Jul 12
Travelodge by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA, 22602
Fully refundableReserve now, pay when you stay
The price is $113 per night from Jul 6 to Jul 7
La Quinta Inn & Suites by Wyndham Winchester
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.

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 $63 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.

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