Photo by Hyelsinta
Search Vacation Homes in Winchester
Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check availability on Vacation Homes in Winchester
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 $107
$208 total
includes taxes & fees
Jun 17 - Jun 18
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, (115)
The price is $295
$518 total
includes taxes & fees
May 29 - May 30
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)
Save an average of 15% on thousands of hotels when you're signed in
Totally renovated downtown home walk to all
Totally renovated downtown home walk to all
9.6 out of 10, Exceptional, (43)
The price is $220
$312 total
includes taxes & fees
May 29 - May 30
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 $109
$229 total
includes taxes & fees
Jun 16 - Jun 17
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, (4)
The price is $251
$430 total
includes taxes & fees
Jun 4 - Jun 5
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)
Luxury Home | Outdoor Deck | Great Location
Luxury Home | Outdoor Deck | Great Location
10.0 out of 10, Exceptional, (55)
The price is $169
$472 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, (81)
Heavenly Home In the Heart of Horse Country
Heavenly Home In the Heart of Horse Country
10.0 out of 10, Exceptional, (42)
The price is $190
$426 total
includes taxes & fees
May 29 - May 30
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 $1,504
$2,303 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 $309
$719 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, (16)
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 29 - May 30
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 $127
$307 total
includes taxes & fees
Jun 17 - Jun 18
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, (1313)
The price is $126
$139 total
includes taxes & fees
Jun 6 - Jun 7
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 $114
$224 total
includes taxes & fees
Jun 12 - Jun 13
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, (97)
The price is $129
$223 total
includes taxes & fees
Jun 16 - Jun 17
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 | 937 |
---|---|
Accommodation | 399 Vacation Homes |
Lowest Price | $107 |
Highest Price | $1,504 |
Recent reviews of Winchester hotelsExpedia verified reviews
5/5 Excellent
"Expedia didn't have listed $75 per clean up fee. Otherwise, nice stay"
A verified traveler stayed at Elwood Hotel & Suites
Posted 16 hours ago
Top Vacation Homes in Other Destinations
More Accommodation Types in Winchester
- Cabin Rentals in Winchester (181)
- Apartments in Winchester (117)
- Condo Rentals in Winchester (51)
- Cottages in Winchester (30)
- RV Parks in Winchester (26)
- Farmstay in Winchester (13)
- Motels in Winchester (13)
- Guest Houses in Winchester (10)
- B&B in Winchester (9)
- Chalets in Winchester (4)
- Resorts in Winchester (1)
- Villas in Winchester (1)
- Hotels (1,199)
All Accommodation Types
Expedia's Latest Trends
Hotels
Top Hotels in RichmondGeorgetown Cheap HotelsNicholasville Cheap HotelsTop Hotels in GeorgetownRichmond Cheap HotelsTop Hotels in FrankfortFrankfort Luxury HotelsTop Hotels in WilmoreFrankfort Pet-friendly HotelsTop Hotels in VersaillesTop Hotels in NicholasvilleGeorgetown Hotels with an Indoor PoolRichmond Hotels with an Indoor PoolFrankfort Cheap HotelsTop Hotels in Midway
Flights
Cars