Compare Winchester Cottage Rentals

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Featured Winchester Cottages

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*

Luray VA
$268 nightly
The price is $309 total per night
$309 total
Dec 1 - Dec 2
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
Secluded, Cozy Cottage in the Shenandoah Valley

Secluded, Cozy Cottage in the Shenandoah Valley

Maurertown VA
Guests staying at this cottage enjoy a hot tub, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
Hunt Country cottage in Upperville!

Hunt Country cottage in Upperville!

Upperville VA
At this cottage, guests have access to features like laundry facilities.
Washer
Dryer
The Vue - Mountain top hot tub overlooking the Shenandoah River

The Vue - Mountain top hot tub overlooking the Shenandoah River

2 out of 5
Front Royal VA
$351 nightly
The price is $387 total per night
$387 total
Dec 9 - Dec 10
Total with taxes and fees
Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills.
Hot Tub
Kitchen
Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance

Shepherdstown WV
At this cottage, guests have access to barbecue grills.
Kitchen
Air conditioning
Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond

Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond

Purcellville VA
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!

Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!

Luray VA
Guests staying at this cottage enjoy a hot tub, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
Hot Tub
Kitchen
CEDAR LANE - Private Cottage, Sophisticated Country Charm

CEDAR LANE - Private Cottage, Sophisticated Country Charm

Middleburg VA
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Carrot Top Cottage surrounded by National Park

Carrot Top Cottage surrounded by National Park

Harpers Ferry WV
At this cottage, guests have access to features like laundry facilities.
Kitchen
Air conditioning
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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.

Hotel Options in Winchester

    Travelodge by Wyndham Winchester

    Travelodge by Wyndham Winchester

    160 Front Royal Pike Winchester VA
    $68 nightly
    The price is $74 total per night from Dec 1 to Dec 2
    $74 total
    Dec 1 - Dec 2
    Total with taxes and fees
    8.4/10 Very Good! (1,093 reviews)
    La Quinta Inn & Suites by Wyndham Winchester

    La Quinta Inn & Suites by Wyndham Winchester

    1055 Millwood Pike, Route 50 East Winchester VA
    $94 nightly
    The price is $102 total per night from Dec 15 to Dec 16
    $102 total
    Dec 15 - Dec 16
    Total with taxes and fees
    9.2/10 Wonderful! (2,226 reviews)
    Microtel Inn & Suites by Wyndham Winchester

    Microtel Inn & Suites by Wyndham Winchester

    150 Faraday Plaza Winchester VA
    $72 nightly
    The price is $78 total per night from Dec 14 to Dec 15
    $78 total
    Dec 14 - Dec 15
    Total with taxes and fees
    9/10 Wonderful! (1,360 reviews)

Cottages

Book a cottage in Winchester
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Winchester. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Winchester better.

Cottage apartments in Winchester range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Winchester
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Winchester and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Winchester cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Winchester. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Winchester Cottages essential information

Accommodation
191 Cottages
Lowest Price
$74
Highest Price
$387
Popular accommodation
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*, Secluded, Cozy Cottage in the Shenandoah Valley, Hunt Country cottage in Upperville!, The Vue - Mountain top hot tub overlooking the Shenandoah River, Quaint Mini Cottage in Shepherdstown - Walking Distance, Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond, Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!, CEDAR LANE - Private Cottage, Sophisticated Country Charm, Carrot Top Cottage surrounded by National Park

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