Compare Winchester Cabin Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Winchester Cabins

Don't see what you're looking for?
See all available properties in Winchester
View all properties
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.

Hotel Options in Winchester

    La Quinta Inn & Suites by Wyndham Winchester

    La Quinta Inn & Suites by Wyndham Winchester

    1055 Millwood Pike, Route 50 East, Winchester, VA, 22602
    The price is $110 per night from Mar 5 to Mar 6
    $110
    per night
    Mar 5 - Mar 6
    4.3/5 Excellent! (1,029 reviews)
    The George Washington Hotel, A Wyndham Grand Hotel

    The George Washington Hotel, A Wyndham Grand Hotel

    103 E Piccadilly St, Winchester, VA, 22601
    The price is $125 per night from Feb 8 to Feb 9
    $125
    per night
    Feb 8 - Feb 9
    4.6/5 Exceptional! (1,023 reviews)
    Travelodge by Wyndham Winchester

    Travelodge by Wyndham Winchester

    160 Front Royal Pike, Winchester, VA, 22602
    The price is $65 per night from Mar 5 to Mar 6
    $65
    per night
    Mar 5 - Mar 6
    3.8/5 Good! (1,041 reviews)

What is the price range for Winchester cabin rentals?


Cabins in Winchester cost from just $65 a night to $389 a night for that something truly special. Prices and availability are subject to change. Additional terms may apply.

What types of Winchester cabin are available?


You might fancy a luxury log cabin retreat for a romantic getaway. Maybe you’re after a family lodge in the woods or a rustic hideaway by the water. With a fantastic selection of 28 unique Winchester cabins to choose from, your perfect escape is just a click away.


How do I find cheap cabin rentals in Winchester?


To see the latest deals on Winchester cabins rentals, enter your travel details and hit search. Arrange your results by price to see the cheapest options first and use the budget filter, map, and ratings to compare cabins. We find prices are often lower during , so this could be the best time to find a cabin bargain.


Why should I choose a Winchester cabin rental?


Picture a cozy space full of personality, space, and privacy. A cabin booked through Orbitz is a place where you can escape the rat race, unwind, and make plans on your private deck, cocooned by trees, water, or views for days. Cook for yourself, just as you like it, share special moments, and build memories.






What amenities will I find in Winchester cabins?


Sink into your outdoor hot tub in a secluded cabin rental or let the kids splash around in a cabin resort’s indoor pool. Our amenities filters make it easy to find cabins in Winchester that deliver those special extras that make all the difference.


How do I find pet-friendly cabins in Winchester?


Click on our pet-friendly filter for woof-tastic Winchester cabins rentals, where your pooch can enjoy a vacation, too. Take walks to dog-happy cafés, explore nature together from sunrise to sundown, then snuggle together in front of a cozy log fire or under the twinkling stars on your deck.


Are there any luxury cabin rentals in Winchester?


To find those luxury cabins with the top-notch touches you’re looking for, use the budget filter, read customer reviews, and dip into the property listings for the details. You can then compare cabins and choose the best cabins for a truly luxurious experience.


How do I find some of the best cabins in Winchester on Orbitz?


Enter your travel details, hit search, and use the filters to see our best deals on cabins in Winchester. Easy! From luxury log cabin rentals to affordable weekend cabin getaways, Orbitz finds your dream cabin in just a few clicks. You can unlock Orbucks when you sign up for Orbitz Rewards, too.