Compare Winchester Cottage Rentals

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Featured Winchester Cottages

1 bed cottage, grill, fire pit, Very close to Red River Gorge!!

1 bed cottage, grill, fire pit, Very close to Red River Gorge!!

Stanton KY
At this cottage, guests have access to barbecue grills.
Pet friendly
Air conditioning
Cozy Cottage Perfect for Girls Night Away

Cozy Cottage Perfect for Girls Night Away

Lexington KY
$737 nightly
The price is $855 total per night
$855 total
Jan 2 - Jan 3
Total with taxes and fees
Guests staying at this cottage enjoy a hot tub and laundry facilities.
Hot Tub
Kitchen
Mountaintop Cottage

Mountaintop Cottage

2 out of 5
Stanton KY
$175 nightly
The price is $193 total per night
$193 total
Jan 3 - Jan 4
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
Unique, Cozy Stay near Red River Gorge

Unique, Cozy Stay near Red River Gorge

Slade KY
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Air conditioning
Laundry
Bungalow | 1 Bed, 0.5 Bath

Bungalow | 1 Bed, 0.5 Bath

Stanton KY
At this cottage, guests have access to barbecue grills.
Kitchen
Pet friendly
3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark

3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark

Georgetown KY
This cottage is a smoke-free cottage.
Kitchen
Air conditioning
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

3 out of 5
Frenchburg KY
$236 nightly
The price is $262 total per night
$262 total
Jan 4 - Jan 5
Total with taxes and fees
This cottage features free WiFi in public areas and barbecue grills. A stay here includes free parking.
Kitchen
Pet friendly
Cozy 1 bedroom cottage on picturesque horse farm

Cozy 1 bedroom cottage on picturesque horse farm

Georgetown KY
Guests staying at this cottage have access to a garden and barbecue grills.
Kitchen
Free WiFi
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY

Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY

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

    Best Western Winchester Hotel

    Best Western Winchester Hotel

    1307 W Lexington Ave Winchester KY
    $72 nightly
    The price is $80 total per night from Jan 6 to Jan 7
    $80 total
    Jan 6 - Jan 7
    Total with taxes and fees
    8.4/10 Very Good! (1,001 reviews)
    Hampton Inn Winchester

    Hampton Inn Winchester

    1025 Early Dr Winchester KY
    $123 nightly
    The price is $136 total per night from Jan 25 to Jan 26
    $136 total
    Jan 25 - Jan 26
    Total with taxes and fees
    9.2/10 Wonderful! (452 reviews)
    Baymont by Wyndham Winchester

    Baymont by Wyndham Winchester

    960 Interstate Dr Winchester KY
    $80 nightly
    The price is $88 total per night from Jan 8 to Jan 9
    $88 total
    Jan 8 - Jan 9
    Total with taxes and fees
    7/10 Good! (772 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
34 Cottages
Lowest Price
$80
Highest Price
$855
Popular accommodation
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!, Cozy Cottage Perfect for Girls Night Away, Mountaintop Cottage , Unique, Cozy Stay near Red River Gorge, Bungalow | 1 Bed, 0.5 Bath, 3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark, Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre, Cozy 1 bedroom cottage on picturesque horse farm, Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY

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