Photo by Hyelsinta

Search Cottages in Winchester

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Cottages in Winchester

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

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

8.8 out of 10, Excellent, (18)
"This cottage was such a great place to come back to after a long day of hiking and exploring Red River Gorge. Super cute in & outside with a beautiful landscape. We also had visits from a local cat every morning and night and he was so extremely sweet and made the trip all the more better."
1 bed cottage, grill, fire pit, Very close to Red River Gorge!!
3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

The price is AED 731
AED 1,595 total
includes taxes & fees
16 Jul - 17 Jul
3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark
Mountaintop Cottage
Terrace/patio

Mountaintop Cottage

2.0 star property
10.0 out of 10, Exceptional, (11)
"The cabin was in an excellent location and was very clean! The host was super helpful with providing directions and answering questions."
The price is AED 514
AED 733 total
includes taxes & fees
21 Jul - 22 Jul
Mountaintop Cottage
Unique, Cozy Stay near Red River Gorge
Exterior

Unique, Cozy Stay near Red River Gorge

8.0 out of 10, Very Good, (4)
"Love it ❤️"
The price is AED 285
AED 535 total
includes taxes & fees
16 Jul - 17 Jul
Unique, Cozy Stay near Red River Gorge
Springside BoHo Getaway
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Springside BoHo Getaway

10.0 out of 10, Exceptional, (45)
"A charming, historic property. Beds are comfy, shower was hot and powerful. 15 mins from the horse park. Perfect for a long stay."
The price is AED 551
AED 1,118 total
includes taxes & fees
16 Jul - 17 Jul
Springside BoHo Getaway
Cozy 1 bedroom cottage on picturesque horse farm
Fridge, microwave, coffee/tea maker, toaster

Cozy 1 bedroom cottage on picturesque horse farm

10.0 out of 10, Exceptional, (36)
"The stay was wonderful. "
Cozy 1 bedroom cottage on picturesque horse farm
Bungalow | 1 Bed, 0.5 Bath
Interior

Bungalow | 1 Bed, 0.5 Bath

10.0 out of 10, Exceptional, (3)
"If you're looking for an off grid sleeping porch in the red river gorge, this one has a nice wooded view."
The price is AED 397
AED 740 total
includes taxes & fees
16 Jul - 17 Jul
Bungalow | 1 Bed, 0.5 Bath
1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!
Pool

1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!

8.4 out of 10, Very Good, (15)
"It was really nice clean.Beautiful place we would definitely stay again."
1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, KY!
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (13)
"Simply a great experience start to finish"
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
House (1 Bedroom) | Interior

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

3.0 star property
The price is AED 496
AED 965 total
includes taxes & fees
17 Jul - 18 Jul
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
House (2 Bedrooms) | Outdoor dining

Peaceful Mt Sterling Cabin: Deck & Fire Pit!

3.0 star property
10.0 out of 10, Exceptional, (1)
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
Lexington Getaway w/ Backyard Deck < 2 Mi to UK!
Interior

Lexington Getaway w/ Backyard Deck < 2 Mi to UK!

3.0 star property
Lexington Getaway w/ Backyard Deck < 2 Mi to UK!
10 Mi to Keeneland: Family Home w/ Deck & Yard
House (3 Bedrooms) | Interior

10 Mi to Keeneland: Family Home w/ Deck & Yard

3.0 star property
10 Mi to Keeneland: Family Home w/ Deck & Yard
Quaint Creekside Cottage w/ Porch & Backyard!
House (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Quaint Creekside Cottage w/ Porch & Backyard!

3.0 star property
Quaint Creekside Cottage w/ Porch & Backyard!
Cozy Cottage Perfect for Girls Night Away
Interior

Cozy Cottage Perfect for Girls Night Away

10.0 out of 10, Exceptional, (9)
"We loved everything about our stay at the charming Lady Clay!! Can't recommend it enough!"
The price is AED 1,135
AED 2,217 total
includes taxes & fees
11 Aug - 12 Aug
Cozy Cottage Perfect for Girls Night Away
Lexington Home ~ 2 Mi to University of Kentucky!
House (3 Bedrooms) | Interior

Lexington Home ~ 2 Mi to University of Kentucky!

3.0 star property
Lexington Home ~ 2 Mi to University of Kentucky!
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
House (3 Bedrooms) | Interior

Georgetown Home ~ 6 Mi to Kentucky Horse Park!

3.0 star property
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Cozy Georgetown Cottage on a Working Horse Farm!
Interior

Cozy Georgetown Cottage on a Working Horse Farm!

10.0 out of 10, Exceptional, (1)
"Had the most wonderful stay what a beautiful place."
Cozy Georgetown Cottage on a Working Horse Farm!
Hike & Climb: Pet-friendly Red River Gorge Cabin!
House (2 Bedrooms) | Interior

Hike & Climb: Pet-friendly Red River Gorge Cabin!

3.0 star property
Hike & Climb: Pet-friendly Red River Gorge Cabin!
Family Home w/ Ping-pong & Fire Pit in Lexington
House (2 Bedrooms) | Interior

Family Home w/ Ping-pong & Fire Pit in Lexington

3.0 star property
Family Home w/ Ping-pong & Fire Pit in Lexington
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Why book your cottage in Winchester with Expedia?
We think that a vacation should be simple, so if you're after cottages in Winchester at a nice price, Expedia has your back. Keep the budget under control and opt for a low-cost option far away from the hustle and bustle, or splurge on an upmarket cottage to pamper your favorite people.
How can I find cheap cottages in Winchester?
With Expedia's useful filter tool, sourcing cheap cottages in Winchester couldn't be simpler. To discover properties that'll make your wallet smile, narrow your search by budget, amenities and star rating.