Photo by Hyelsinta

Search Winchester Cottage Rentals

    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
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Cottages in Winchester

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Interior

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

3.0 star property
The price is S$297
includes taxes & fees
27 Jul - 28 Jul
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
Situated in a natural setting, this cabin features a rustic exterior with a steeply pitched roof and a front porch.

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!
Enjoy the peaceful atmosphere of this two-story house with a spacious porch and covered deck, surrounded by a well-manicured lawn.

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
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
Quaint Creekside Cottage w/ Porch & Backyard!
Enjoy a peaceful stay in this charming single-story house with a cozy porch and beautiful views of the surrounding lawn and trees.

Quaint Creekside Cottage w/ Porch & Backyard!

3.0 star property
Quaint Creekside Cottage w/ Porch & Backyard!
Lexington Home ~ 2 Mi to University of Kentucky!
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!
Stroll up to this charming single-story home with a cozy front porch and inviting windows.

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

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

3.0 star property
Family Home w/ Ping-pong & Fire Pit in Lexington
Walk to UK Campus: Charming Home w/ Patio!
Interior

Walk to UK Campus: Charming Home w/ Patio!

3.0 star property
Walk to UK Campus: Charming Home w/ Patio!
Lovely Lexington Home: 4 Mi to Downtown!
Situated in a quiet suburban neighborhood, this single-story home features a gabled roof and a front garage.

Lovely Lexington Home: 4 Mi to Downtown!

3.0 star property
Lovely Lexington Home: 4 Mi to Downtown!
Cozy Georgetown Cottage on a Working Horse Farm!
Interior

Cozy Georgetown Cottage on a Working Horse Farm!

3.0 star property
Cozy Georgetown Cottage on a Working Horse Farm!
15 Mi to Dtwn Lexington: Serene Wilmore Home!
Traditional home with a charming front porch and serene surroundings.

15 Mi to Dtwn Lexington: Serene Wilmore Home!

3.0 star property
15 Mi to Dtwn Lexington: Serene Wilmore Home!
Lexington Family Home ~ 2 Miles to UK Campus!
Stroll up the pathway to this charming home, featuring a cozy chimney and a welcoming front door.

Lexington Family Home ~ 2 Miles to UK Campus!

3.0 star property
Lexington Family Home ~ 2 Miles to UK Campus!
Historic & Spacious Family Home in Nicholasville!
Stately building with a central pediment and columns, set amidst a beautifully manicured lawn and stone pathway.

Historic & Spacious Family Home in Nicholasville!

3.0 star property
Historic & Spacious Family Home in Nicholasville!
Cozy Cabin w/ Hot Tub in Heart of Red River Gorge!
Exterior

Cozy Cabin w/ Hot Tub in Heart of Red River Gorge!

3.0 star property
Cozy Cabin w/ Hot Tub in Heart of Red River Gorge!
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

Top Winchester Hotel Reviews

GuestHouse Lexington

GuestHouse Lexington

10/10 Excellent
"Front desk staff was amazing made the experience painless & easy great place to stay all around if u need a place to stay during a trip make this hotel your first stop"
Stejeta 1-night trip
Posted 16 hours ago
GuestHouse Lexington

Frequently asked questions

Why book your cottage in Winchester with Expedia?
We think that a holiday 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 favourite 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.
What is there to do in Winchester near my cottage?
The most useful travel accessory is a well-planned schedule. Southwind Golf Course is a good spot to start your adventures in Winchester.