Compare Winchester Cottage Rentals

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Featured Cottages in Winchester

Hattingh Equine Rescue Launches Farm Cottage Stay to Support Rescued Horses

Hattingh Equine Rescue Launches Farm Cottage Stay to Support Rescued Horses

Purcellville VA
Guests staying at this cottage can enjoy an outdoor pool, barbecue grills, and a garden. This smoke-free cottage also has a water dispenser.
Pool
Kitchen
LIFE IS BETTER AT THE SHENANDOAH RIVER AT OUR COZY RIVERFRONT COTTAGE!!

LIFE IS BETTER AT THE SHENANDOAH RIVER AT OUR COZY RIVERFRONT COTTAGE!!

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

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

Luray VA
This cottage features a hot tub and a garden. This smoke-free cottage also has barbecue grills.
Hot Tub
Kitchen
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, a garden, and barbecue grills.
Kitchen
Washer
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
Cozy Retreat - Hot tub + Mountain Views + Pets

Cozy Retreat - Hot tub + Mountain Views + Pets

Fort Valley 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
Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!

Harpers Ferry WV
$458 nightly
The price is $509 total per night
$509 total
Sep 9 - Sep 10
Total with taxes and fees
Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills.
Hot Tub
Kitchen
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.
Hot Tub
Kitchen
18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg

Middleburg VA
$370 nightly
The price is $397 total per night
$397 total
Sep 3 - Sep 4
Total with taxes and fees
Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Pet friendly
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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

    Spark by Hilton Winchester

    Spark by Hilton Winchester

    150 Wingate Dr Winchester VA
    $77 nightly
    The price is $87 total per night from Sep 13 to Sep 14
    $87 total
    Sep 13 - Sep 14
    Total with taxes and fees
    9.2/10 Wonderful! (1,001 reviews)
    Holiday Inn Winchester Se-Historic Gateway by IHG

    Holiday Inn Winchester Se-Historic Gateway by IHG

    333 Front Royal Pike Winchester VA
    $104 nightly
    The price is $115 total per night from Sep 6 to Sep 7
    $115 total
    Sep 6 - Sep 7
    Total with taxes and fees
    The George Washington Hotel, A Wyndham Grand Hotel

    The George Washington Hotel, A Wyndham Grand Hotel

    103 E Piccadilly St Winchester VA
    $130 nightly
    The price is $148 total per night from Sep 8 to Sep 9
    $148 total
    Sep 8 - Sep 9
    Total with taxes and fees
    9.4/10 Exceptional! (1,000 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
189 Cottages
Lowest Price
$87
Highest Price
$509
Popular accommodation
 Hattingh Equine Rescue Launches Farm Cottage Stay to Support Rescued Horses, LIFE IS BETTER AT THE SHENANDOAH RIVER AT OUR COZY RIVERFRONT COTTAGE!!, Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!, RIVERKEEPER INN, Waterfront Property on the Potomac River , Hunt Country cottage in Upperville!, Cozy Retreat - Hot tub + Mountain Views + Pets, Peaceful Lakefront Cottage with Mountain Views!, Secluded Cottage on 10 Acres. Close to Shen. Natl. Park and Luray Caverns, 18th Century Stone Cottage minutes from historic Middleburg

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