Compare Winchester Cottage Rentals

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Featured Cottages in Winchester

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

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

Luray VA
$274 nightly
The price is $316 total per night
$316 total
Mar 24 - Mar 25
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
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.
RIVERKEEPER INN, Waterfront Property on the Potomac River

RIVERKEEPER INN, Waterfront Property on the Potomac River

Harper's Ferry WV
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns

Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns

Luray VA
Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills.
Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Harpers Ferry WV
$292 nightly
The price is $325 total per night
$325 total
Mar 24 - Mar 25
Total with taxes and fees
Guests staying at this cottage have access to barbecue grills and a garden.
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 barbecue grills. This smoke-free cottage also has a garden.
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

Hamilton VA
$344 nightly
The price is $392 total per night
$392 total
Mar 26 - Mar 27
Total with taxes and fees
Guests of this cottage have access to a hot tub.
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, a garden, and barbecue grills.
Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond

Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond

Purcellville VA
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
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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

    Holiday Inn Winchester Se-Historic Gateway by IHG

    Holiday Inn Winchester Se-Historic Gateway by IHG

    333 Front Royal Pike Winchester VA
    $98 nightly
    The price is $106 total per night from Mar 29 to Mar 30
    $106 total
    Mar 29 - Mar 30
    Total with taxes and fees
    9/10 Wonderful! (1,003 reviews)
    La Quinta Inn & Suites by Wyndham Winchester

    La Quinta Inn & Suites by Wyndham Winchester

    1055 Millwood Pike, Route 50 East Winchester VA
    $104 nightly
    The price is $114 total per night from Apr 20 to Apr 21
    $114 total
    Apr 20 - Apr 21
    Total with taxes and fees
    9.2/10 Wonderful! (2,276 reviews)
    Sleep Inn & Suites Winchester near University

    Sleep Inn & Suites Winchester near University

    140 Costello Dr Winchester VA
    $76 nightly
    The price is $83 total per night from Apr 20 to Apr 21
    $83 total
    Apr 20 - Apr 21
    Total with taxes and fees
    7.8/10 Good! (1,001 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
$83
Highest Price
$392
Popular accommodation
Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*, CEDAR LANE - Private Cottage, Sophisticated Country Charm, RIVERKEEPER INN, Waterfront Property on the Potomac River , Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns, Amazing dog-friendly cottage. Walk 2 Harpers Ferry, Secluded, Cozy Cottage in the Shenandoah Valley, The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!, Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond, Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond

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