Compare Winchester Cottage Rentals

Start date: Check-in selected.
To Date
End date: Check-out

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 Cottages

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

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

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

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

$283 nightly
The price is $326 total per night
$326 total
Oct 29 - Oct 30
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

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
Hunt Country cottage in Upperville!

Hunt Country cottage in Upperville!

At this cottage, guests have access to features like laundry facilities.
Washer
Dryer
Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers

$383 nightly
The price is $426 total per night
$426 total
Oct 5 - Oct 6
Total with taxes and fees
At this cottage, guests have access to an arcade/game room, laundry facilities, and barbecue grills.
Kitchen
Washer
Historical cottage in the town of Paris

Historical cottage in the town of Paris

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Cozy Retreat - Hot tub + Mountain Views + Pets

Cozy Retreat - Hot tub + Mountain Views + Pets

$252 nightly
The price is $278 total per night
$278 total
Oct 5 - Oct 6
Total with taxes and fees
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

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

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

    Hampton Inn Winchester-University/Mall Area

    Hampton Inn Winchester-University/Mall Area

    640 East Jubal Early Drive, Winchester, VA
    $106 nightly
    The price is $120 total per night from Nov 2 to Nov 3
    $120 total
    Nov 2 - Nov 3
    Total with taxes and fees
    9/10 Wonderful! (1,007 reviews)
    La Quinta Inn & Suites by Wyndham Winchester

    La Quinta Inn & Suites by Wyndham Winchester

    1055 Millwood Pike, Route 50 East, Winchester, VA
    $108 nightly
    The price is $118 total per night from Nov 2 to Nov 3
    $118 total
    Nov 2 - Nov 3
    Total with taxes and fees
    9.2/10 Wonderful! (2,167 reviews)
    Travelodge by Wyndham Winchester

    Travelodge by Wyndham Winchester

    160 Front Royal Pike, Winchester, VA
    $69 nightly
    The price is $75 total per night from Nov 2 to Nov 3
    $75 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.4/10 Very Good! (1,100 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
192 Cottages
Lowest Price
$75
Highest Price
$426
Popular accommodation
Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!, Cottage by the Caverns *FIRE PIT* *MOUNTAIN VIEWS*, Secluded, Cozy Cottage in the Shenandoah Valley, Hunt Country cottage in Upperville!, Quiet Cottage on Five+ Acres of Woods Close to All That Berkeley Springs Offers, Historical cottage in the town of Paris, Cozy Retreat - Hot tub + Mountain Views + Pets, CEDAR LANE - Private Cottage, Sophisticated Country Charm, Charming Cottage in Purcellville on 12 Gorgeous Acres with 2 Acre Stocked Pond

Explore More Ways to Travel with Travelocity

Explore More Ways to Travel with Travelocity