Photo by Hyelsinta

Search Cottages in Winchester

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

In two weeks
3 Oct - 5 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec
In four months
9 Jan - 11 Jan

Cottages in Winchester

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

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

8.4 out of 10, Very Good, (22)
"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!!
Mountaintop Cottage
Exterior

Mountaintop Cottage

2.0 star property
10.0 out of 10, Exceptional, (17)
"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 SAR 506
SAR 724 total
includes taxes & fees
1 Oct - 2 Oct
Mountaintop Cottage
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Exterior

Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!

10.0 out of 10, Exceptional, (280)
"This is an adorable property on a beautiful farm! Hosts were very kind and attentive. We will definitely stay here the next time we are in Lexington! "
Charming Cottage Home On A Farm In The Kentucky Horse Country! Relax!
Cozy Cottage Perfect for Girls Night Away
Interior

Cozy Cottage Perfect for Girls Night Away

9.8 out of 10, Exceptional, (10)
"This place is just charming. We were in town for our daughter’s graduation from UK and your place was perfect. Spacious and so comfy. "
Cozy Cottage Perfect for Girls Night Away
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

10.0 out of 10, Exceptional, (3)
"Great stay! Will be back again. "
3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark
Cozy 1 bedroom cottage on picturesque horse farm
Exterior

Cozy 1 bedroom cottage on picturesque horse farm

10.0 out of 10, Exceptional, (40)
"Great stay, would do it gain for sure "
Cozy 1 bedroom cottage on picturesque horse farm
Unique, Cozy Stay near Red River Gorge
Exterior

Unique, Cozy Stay near Red River Gorge

7.0 out of 10, Good, (8)
"Me and my girlfriend had a great time enjoy the area around were we were staying and had a great time and the people their were nice"
The price is SAR 291
SAR 546 total
includes taxes & fees
5 Oct - 6 Oct
Unique, Cozy Stay near Red River Gorge
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!

8.8 out of 10, Excellent, (18)
"It was really nice clean.Beautiful place we would definitely stay again."
1,600 Acres | Pool | Pond | Fishing | | WiFi near Red River Gorge, 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
10.0 out of 10, Exceptional, (1)
"The cabin was adorable and had everything we needed for a weekend getaway. The host was very responsive, and we had a wonderful trip! "
The price is SAR 506
SAR 985 total
includes taxes & fees
22 Oct - 23 Oct
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
Exterior

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!
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!
Location! Comfy Beds~Hot Tub~6mi KY Horse Park~Walkable
Exterior

Location! Comfy Beds~Hot Tub~6mi KY Horse Park~Walkable

Location! Comfy Beds~Hot Tub~6mi KY Horse Park~Walkable
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
Exterior

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
Springside BoHo Getaway
Exterior

Springside BoHo Getaway

10.0 out of 10, Exceptional, (48)
"Jonathon provided a great stay. "
Springside BoHo Getaway
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
House (3 Bedrooms) | Front of property

Georgetown Home ~ 6 Mi to Kentucky Horse Park!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice property, very clean."
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Lexington Getaway w/ Backyard Deck < 2 Mi to UK!
House (3 Bedrooms) | Interior

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

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

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

3.0 star property
10.0 out of 10, Exceptional, (1)
"I liked the porch and the pergola. My granddaughter ran around the house in bare feet and her feet got incredibly dirty. Floors probably need a good cleaning. That was the only begative i had."
10 Mi to Keeneland: Family Home w/ Deck & Yard
Lovely Lexington Home: 4 Mi to Downtown!
House (4 Bedrooms) | Interior

Lovely Lexington Home: 4 Mi to Downtown!

3.0 star property
Lovely Lexington Home: 4 Mi to Downtown!
Quaint Creekside Cottage w/ Porch & Backyard!
Interior

Quaint Creekside Cottage w/ Porch & Backyard!

3.0 star property
Quaint Creekside Cottage w/ Porch & Backyard!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

GLō Best Western Lexington

GLō Best Western Lexington

10/10 Excellent
"Love the place "
Alfredo 1-night trip
Posted 2 days ago
GLō Best Western Lexington

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.