Compare Winchester Cottage Rentals

Featured Cottages in Winchester

Hattingh Equine Rescue Launches Farm Cottage Stay to Support Rescued Horses

Guests staying at this cottage can enjoy an outdoor pool, a water dispenser, and barbecue grills. This smoke-free cottage also has a garden.

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.

Cozy Retreat - Hot tub + Mountain Views + Pets

$237 nightly

$262 total

Jul 26 - Jul 27

Total with taxes and fees

Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.

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

This cottage features a hot tub and barbecue grills. This smoke-free cottage also has a garden.

RIVERKEEPER INN, Waterfront Property on the Potomac River

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

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

$321 nightly

$370 total

Jul 30 - Jul 31

Total with taxes and fees

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.

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

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

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

Guests staying at this cottage have access to a garden and barbecue grills.

At this cottage, guests have access to features like laundry facilities.

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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

333 Front Royal Pike Winchester VA

$86 nightly

$95 total

Aug 2 - Aug 3

Total with taxes and fees

9.2/10 Wonderful! (1,005 reviews)

TRU By Hilton Winchester

118 Mercedes Court Winchester VA

$81 nightly

$90 total

Jul 26 - Jul 27

Total with taxes and fees

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St Winchester VA

$122 nightly

$138 total

Jul 26 - Jul 27

Total with taxes and fees

9.4/10 Exceptional! (1,005 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	186 Cottages
Lowest Price	$90
Highest Price	$370
Popular accommodation	Hattingh Equine Rescue Launches Farm Cottage Stay to Support Rescued Horses, Secluded, Cozy Cottage in the Shenandoah Valley, Cozy Retreat - Hot tub + Mountain Views + Pets, Charming Cottage, Fresh Eggs, Friendly Pets AND Pet Friendly!, RIVERKEEPER INN, Waterfront Property on the Potomac River , Cottage by the Caverns FIRE PIT MOUNTAIN VIEWS, Charming 2-Bedroom Cottage in Loudoun Co, VA on 12 Gorgeous Acres w/ 2-Acre Pond, LIFE IS BETTER AT THE SHENANDOAH RIVER AT OUR COZY RIVERFRONT COTTAGE!!, Bear Mountain Cottage