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Search results; Over 1,000 places in Winchester

Guest favorite
Home in Winchester
Cozy Cottage
1 queen bed
May 12 – 17
4.91 out of 5 average rating, 672 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
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
Home in Winchester
NEW Serene Country Refuge at The Right Angle
4 beds
Apr 19 – 24
5.0 out of 5 average rating, 13 reviews
Guest favorite
Farm stay in Winchester
Renovated historic home on working cattle farm
2 beds
Apr 28 – May 3
4.88 out of 5 average rating, 42 reviews
Guest favorite
Apartment in Winchester
The Carriage Inn - 1-bdrm apt in historic downtown
1 queen bed
Apr 19 – 24
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
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
Guesthouse in Winchester
Carriage House on the Park
1 queen bed
May 22 – 27
4.95 out of 5 average rating, 159 reviews
Guest favorite
Home in Winchester
Cute 2 Story Home in Winchester
4 beds
Jun 21 – 26
5.0 out of 5 average rating, 13 reviews
Superhost
Farm stay in Winchester
The Winchester Retreat
1 bed
May 9 – 14
4.86 out of 5 average rating, 43 reviews
Guest favorite
Farm stay in Winchester
LenMar Farm Country Stay near Lexington KY
3 beds
Jun 18 – 23
4.93 out of 5 average rating, 106 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
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
Superhost
Home in Winchester
The Winchester 2
5 beds
May 5 – 10
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Winchester
River Relaxation -3king beds
3 beds
May 18 – 23
4.82 out of 5 average rating, 39 reviews
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
Guest favorite
Cabin in Mount Sterling
The Honey Hut, Think of “ On Golden Pond"
2 beds
Apr 21 – 26
4.96 out of 5 average rating, 202 reviews