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Compare 399 Vacation Homes in Winchester with updated reviews, rates, and availability.
Stay in a 1953 Gunnison Home is within walking distance to St Joe Hospital
Stay in a 1953 Gunnison Home is within walking distance to St Joe Hospital
9.2 out of 10, Wonderful, (18)
The price is $100
$203 total
includes taxes & fees
May 27 - May 28
Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location
Morrison Cabin Offers The Finest Interiors, Unique History & Very Best Location
10.0 out of 10, Exceptional, (114)
The price is $295
$515 total
includes taxes & fees
May 26 - May 27
3 Bdr/3 Bath House in Andover Convenient to All of Lexington
3 Bdr/3 Bath House in Andover Convenient to All of Lexington
10.0 out of 10, Exceptional, (263)
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Totally renovated downtown home walk to all
Totally renovated downtown home walk to all
9.6 out of 10, Exceptional, (40)
The price is $220
$312 total
includes taxes & fees
May 27 - May 28
Stylish 2Bed/2Bath - Close to I-75 and EKU
Stylish 2Bed/2Bath - Close to I-75 and EKU
10.0 out of 10, Exceptional, (17)
The price is $124
$246 total
includes taxes & fees
May 27 - May 28
Isla's Landing - Charming Historic 1940s Home
Isla's Landing - Charming Historic 1940s Home
10.0 out of 10, Exceptional, (18)
Victorian glory in downtown Georgetown. Close to Horse Park and College.
Victorian glory in downtown Georgetown. Close to Horse Park and College.
10.0 out of 10, Exceptional, (3)
The price is $251
$428 total
includes taxes & fees
May 27 - May 28
The Wellington: Fire-pit; Walk to EKU & Town by I-75
The Wellington: Fire-pit; Walk to EKU & Town by I-75
9.8 out of 10, Exceptional, (61)
The price is $150
$265 total
includes taxes & fees
Jun 3 - Jun 4
5 Star Location | Walk to Downtown | Patio | Fire Pit
5 Star Location | Walk to Downtown | Patio | Fire Pit
10.0 out of 10, Exceptional, (137)
The price is $171
$486 total
includes taxes & fees
Jun 3 - Jun 4
Luxury Home | Outdoor Deck | Great Location
Luxury Home | Outdoor Deck | Great Location
10.0 out of 10, Exceptional, (55)
The price is $169
$470 total
includes taxes & fees
May 30 - May 31
Cinderella’s Guest House
Cinderella’s Guest House
10.0 out of 10, Exceptional, (63)
Newly renovated Historic House within walking distance to UK.
Newly renovated Historic House within walking distance to UK.
10.0 out of 10, Exceptional, (80)
Heavenly Home In the Heart of Horse Country
Heavenly Home In the Heart of Horse Country
10.0 out of 10, Exceptional, (41)
The price is $190
$426 total
includes taxes & fees
May 26 - May 27
Cozy Modern 3-bd, Pet Friendly, 12 miles from RRG!
Cozy Modern 3-bd, Pet Friendly, 12 miles from RRG!
10.0 out of 10, Exceptional, (19)
7 Bedrooms | 6.5 Bathrooms |Hot Tub | 10 Beds
7 Bedrooms | 6.5 Bathrooms |Hot Tub | 10 Beds
10.0 out of 10, Exceptional, (19)
The price is $1,694
$2,546 total
includes taxes & fees
Jun 21 - Jun 22
Hot Tub | Great Location |Patio| Grill | Tempurpedic Beds
Hot Tub | Great Location |Patio| Grill | Tempurpedic Beds
10.0 out of 10, Exceptional, (37)
The price is $299
$706 total
includes taxes & fees
Jun 12 - Jun 13
Lexington Vacation Home ~ 6 Mi to Horse Park!
Lexington Vacation Home ~ 6 Mi to Horse Park!
10.0 out of 10, Exceptional, (15)
Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8
Bourbon Run - HotTub/ Ark 30min/ Horse Park 12min/ Walk Downtown/ 4BR Sleeps 8
10.0 out of 10, Exceptional, (3)
The price is $185
$359 total
includes taxes & fees
May 28 - May 29
Lovely 3 Bdrm Home w/Free Parking Close to I-75!
Lovely 3 Bdrm Home w/Free Parking Close to I-75!
10.0 out of 10, Exceptional, (9)
Mid-Century 3 BR In Heart of Downtown Lex
Mid-Century 3 BR In Heart of Downtown Lex
9.6 out of 10, Exceptional, (18)
The price is $126
$307 total
includes taxes & fees
May 27 - May 28
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.
Other property types in Winchester
Natural Bridge State Resort Park
Natural Bridge State Resort Park
8.6 out of 10, Excellent, (1308)
The price is $126
$139 total
includes taxes & fees
May 23 - May 24
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
Hot Tub & WiFi - Family Log Cabin - Cozy Canopy - Red River Gorge, Kentucky!
9.8 out of 10, Exceptional, (242)
The price is $152
$269 total
includes taxes & fees
Jun 6 - Jun 7
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
Upscale Shipping Container Cabin in the Woods of Red River Gorge-HOT TUB
10.0 out of 10, Exceptional, (96)
The price is $139
$236 total
includes taxes & fees
Jun 6 - Jun 7
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.
Winchester Vacation Homes information
Number of reviews | 933 |
---|---|
Accommodation | 399 Vacation Homes |
Lowest Price | $100 |
Highest Price | $1,694 |
Recent reviews of Winchester hotelsExpedia verified reviews
5/5 Excellent
"The free snacks were a great addition!"
A verified traveler stayed at Embassy Suites by Hilton Lexington Green
Posted 12 hours ago
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