Photo by Nawa Aseen
Search Vacation Homes in Winchester
Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
OneKeyCashEarn OneKeyCash on all your eligible bookings
Upfront pricingWe are not like the others - we include taxes and fees
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Our top choices for Winchester vacation homes
River Relaxation - Calm Riverfront Home in Winchester Kentucky
River Relaxation - Calm Riverfront Home in Winchester KentuckyWinchester
7.0 out of 10, Good, (4)
"We loved the house, the hosts were great and super communicative! The house is also close to Lexington and Winchester so we had plenty to do and places to eat out! "
Maeve R.
$311 nightly
The price is $343
Dec 28 - Dec 29
Total with taxes and fees
Cozy Tiny Home Retreat - Near RRG Hiking + Hot Tub
Cozy Tiny Home Retreat - Near RRG Hiking + Hot TubStanton
10.0 out of 10, Exceptional, (1)
"Perfect small cozy cabin for a couple get away. Thank you. We really enjoyed our stay."
Carrie F.
$177 nightly
The price is $195
Dec 25 - Dec 26
Total with taxes and fees
Charming Kentucky Stone House
Charming Kentucky Stone HouseLexington
10.0 out of 10, Exceptional, (4)
"My wife and daughter stayed and said it was nice, clean, and easy to navigate, too. They would stay again!"
Justin M.
$205 nightly
The price is $238
Jan 5 - Jan 6, 2026
Total with taxes and fees
My Old Kentucky Home
My Old Kentucky HomeLexington
10.0 out of 10, Exceptional, (27)
"Cool property, with a great location. Owner had great communication."
Anonymous traveler
$213 nightly
The price is $247
Dec 29 - Dec 30
Total with taxes and fees
Cozy 1-bedroom in Lexington
Cozy 1-bedroom in LexingtonLexington
9.2 out of 10, Wonderful, (10)
"The property was clean and well kept, the location is perfect and communication was immediate. I will definitely rent again!"
Becky S.
$194 nightly
The price is $225
Jan 1 - Jan 2, 2026
Total with taxes and fees
Peregrine Cabin - Off the Grid, hike-in cabin
Peregrine Cabin - Off the Grid, hike-in cabinStanton
10.0 out of 10, Exceptional, (13)
"We absolutely loved being tucked into the woods. We had a great experience and it was the perfect trip for our anniversary. "
Kenetra F.
$162 nightly
The price is $176
Dec 26 - Dec 27
Total with taxes and fees
Pet-Friendly Bluegrass Retreat w/ Fenced Yard
Pet-Friendly Bluegrass Retreat w/ Fenced YardGeorgetown
9.4 out of 10, Exceptional, (28)
"Cute quaint neighborhood, big back yard space, host very responsive. "
Jenny M.
$178 nightly
The price is $196
Jan 24 - Jan 25, 2026
Total with taxes and fees
Hot Tub Glow Hill Home Near KY Horse Park, Ark and Rupp Arena
Hot Tub Glow Hill Home Near KY Horse Park, Ark and Rupp ArenaGeorgetown
10.0 out of 10, Exceptional, (3)
"Enjoyed my stay. Hosts were easy to communicate with and the rental was clean and quiet. "
Barton
$233 nightly
The price is $256
Dec 26 - Dec 27
Total with taxes and fees
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.
Find vacation rentals that suit your style
Cabins
Aparthotels
Save an average of 15% on thousands of hotels when you're signed in
Top Winchester Hotel Reviews
Embassy Suites by Hilton Lexington Green
10/10 Excellent
Find out more about Winchester
Winchester Vacation Homes information
Number of reviews | 418 |
|---|---|
Accommodation | 437 Vacation Homes |
Lowest Price | $132 |
Highest Price | $343 |
Explore a world of travel with Expedia
- Hotels near Bluegrass Heritage Museum
- Hotels near Community Park
- Hotels near Clark Regional Medical Center
- Hotels near Lykins Park
- Hotels near Southwind Golf Course
- Hotels near Cassell Creek Golf Course
- Hotels near Kentucky River Museum
- Hotels near Fort Boonesborough State Park
- Hotels near Grimes Mill Winery
- Hotels near Kentucky River
- Lexington Hotels
- Hotels near W S Webb Museum of Anthropology
- Hotels near Hamburg Pavilon
- Cabin Rentals in Mount Sterling
- RV Parks in Mount Sterling
- B&B in Mount Sterling
- Motels in Mount Sterling
- Apartments in Mount Sterling
- Cottages in Mount Sterling
- Condo Rentals in Mount Sterling
- Farmstay in Mount Sterling
- Hotels near Raven Run Nature Sanctuary
- Hotels near Jacobson Park
- Mount Sterling Hotels
- Hotels near Hamburg Place
- Hotels near Liberty Area
- Hotels with a Pool in Mount Sterling
- Pet-friendly Hotels in Mount Sterling
- Hotels with Hot Tubs in Mount Sterling
- Hotels with smoking rooms in Mount Sterling
- 4 Star Hotels in Mount Sterling
- Luxury Hotels in Mount Sterling
- 3 Star Hotels in Mount Sterling
- Marriott Hotels & Resorts in Mount Sterling
- Hilton Hotels in Mount Sterling
- Hotels with a Gym in Mount Sterling
- Hotels with an Outdoor Pool in Mount Sterling
- Family Hotels in Mount Sterling
- Hotels with Connecting Rooms in Mount Sterling
- Red Roof Inn Hotels in Mount Sterling
- Extended Stay Hotels in Mount Sterling
- Hotel Wedding Venues Hotels in Mount Sterling
- Best Western Hotels in Mount Sterling
- Resorts & Hotels with Spas in Mount Sterling
- Non-Smoking Hotels in Mount Sterling
- Hotels with an Indoor Pool in Mount Sterling
- Hotels near Claiborne Farm
- Hotels near The Thoroughbred Center
- Hotels near Lexington Ice Center
- Cabin Rentals in Paris
- Apartments in Paris
- Motels in Paris
- B&B in Paris
- Cottages in Paris
- Vacation Homes in Paris
- Hotels near Talon Winery
- Hotels near Hopewell Museum
- Paris Hotels
- Hotels near The Cane Ridge Meeting House
- Camargo Hotels
- Bluegrass Heritage Museum
- Lykins Park
- Southwind Golf Course
- Cassell Creek Golf Course
- Fort Boonesborough State Park
- Boone Station State Historic Site
- Grimes Mill Winery
- Raven Run Nature Sanctuary
- Jacobson Park
- Visit Mount Sterling
- Mount Sterling Vacations
- White Hall State Historic Site
- Claiborne Farm
- The Thoroughbred Center
- Lexington Ice Center
- Talon Winery
- Hopewell Museum
- The Cane Ridge Meeting House
- Nannine Clay Wallis Arboretum
- Visit Paris
- Car rentals near Lykins Park
- Car rentals near Clintonville
- Car rentals near North Middletown
- Car rentals near Hamburg Pavilon
- Car rentals near Mount Sterling
- Enterprise Rental Cars in Mount Sterling
- Hertz Rental Cars in Mount Sterling
- Budget Rental Cars in Mount Sterling
- Luxury Car Rentals in Mount Sterling
- Car rentals near The Thoroughbred Center
- Car rentals near Camargo
- Car rentals near Paris