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Search results; Over 1,000 homes in Winchester

Apartment in Winchester
The Winchester Cozy One Bedroom!
1 queen bed
Apr 30 – May 5
4.7 out of 5 average rating, 20 reviews
Superhost
Home in Winchester
River Relaxation -3king beds
3 beds
May 18 – 23
4.82 out of 5 average rating, 39 reviews
Home in Winchester
Wi-Fi - Office Space - Full Gym Access - Park View
Apr 19 – 24
New place to stay
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
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
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
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
LenMar Farm Country Stay near Lexington KY
3 beds
Jun 18 – 23
4.93 out of 5 average rating, 106 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
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 Irvine
Pauline's Paradise
3 beds
Apr 20 – 25
5.0 out of 5 average rating, 45 reviews
Guest favorite
Home in Winchester
Grammys getaway
3 beds
May 5 – 10
4.95 out of 5 average rating, 20 reviews
Guest favorite
Cottage in Clay City
Scenic views, farm fun in peaceful modern cottage
3 beds
Apr 29 – May 4
4.97 out of 5 average rating, 92 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
Tiny home in Richmond
Tiny Home; Mini Farm Getaway
May 7 – 12
5.0 out of 5 average rating, 12 reviews
Guest favorite
Cabin in Richmond
Private cabin on KY River/Hot tub/30 miles to Lex
5 beds
May 12 – 17
4.96 out of 5 average rating, 49 reviews
Guest favorite
Treehouse in Georgetown
Treehouse with TWO outdoor tubs by the creek!
1 bed
Apr 28 – May 3
4.98 out of 5 average rating, 86 reviews
Superhost
Home in Winchester
The River House
4 beds
May 4 – 9