%{visible} of %{smart_count_str} Airbnb Category showing||||%{visible} of %{smart_count_str} Airbnb Categories showing
Display total before taxes

Search results; Over 1,000 homes in Winchester

Guest favorite
Apartment in Winchester
Whimsical Winchester Apartment!
1 queen bed
Apr 28 – May 3
4.93 out of 5 average rating, 14 reviews
Guest favorite
Apartment in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 queen bed
Apr 20 – 25
4.93 out of 5 average rating, 73 reviews
Guest favorite
Guesthouse in Winchester
Escape and unwind in the country
2 beds
May 6 – 11
4.98 out of 5 average rating, 174 reviews
Apartment in Winchester
2nd Story Historic Downtown 2 BR w Modern Comforts
2 queen beds
Apr 28 – May 3
4.65 out of 5 average rating, 80 reviews
Guest favorite
Loft in Winchester
Stylish Loft Historic Downtown 2Bdrm Winchester KY
2 beds
Apr 28 – May 3
4.98 out of 5 average rating, 57 reviews
Guest favorite
Apartment in Winchester
The River House Floor 2 Getaway, w/a river view.
1 king bed
May 5 – 10
4.92 out of 5 average rating, 99 reviews
Guest favorite
Home in Winchester
Cute 2 Story Home in Winchester
4 beds
May 13 – 18
5.0 out of 5 average rating, 13 reviews
Guest favorite
Farm stay in Winchester
2Rm*Farm Cottage*Comfy King * DT Winchester 5 min.
2 beds
Apr 21 – 26
5.0 out of 5 average rating, 54 reviews
Guest favorite
Farm stay in Winchester
Family Farm Winchester/Lexington 20 min.*Game Room
8 beds
May 6 – 11
4.97 out of 5 average rating, 87 reviews
Guest favorite
Home in Mount Sterling
THE DOLLY - Cozy, Bright Home in Historic Downtown
1 queen bed
Apr 27 – May 2
4.96 out of 5 average rating, 139 reviews
Superhost
Home in Winchester
The Winchester 2
5 beds
May 5 – 10
5.0 out of 5 average rating, 4 reviews
Guest favorite
Guesthouse in Winchester
Carriage House Gardenside
1 king bed
May 17 – 22
4.96 out of 5 average rating, 54 reviews
Superhost
Home in Winchester
The Winchester
5 beds
May 5 – 10
5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in Winchester
Grammys getaway
3 beds
May 5 – 10
4.95 out of 5 average rating, 20 reviews
Guest favorite
Loft in Winchester
Hanna’s 1,400 SQ FT Downtown Royal Retreat Loft
2 beds
Apr 20 – 25
5.0 out of 5 average rating, 12 reviews
Guest favorite
Cabin in Waco
Stunning Cedar Cabin, Hot Tub, Amazing Views!
1 king bed
Jun 17 – 22
5.0 out of 5 average rating, 57 reviews
Home in Winchester
Wi-Fi - Office Space - Full Gym Access - Park View
Apr 20 – 25
New place to stay
Guest favorite
Home in Winchester
Peacock Ranch House - Lexington and Winchester
3 queen beds
Apr 20 – 25
5.0 out of 5 average rating, 22 reviews