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 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 AED 397
AED 768 total
includes taxes & fees
17 Jun - 18 Jun
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 AED 1,084
AED 1,901 total
includes taxes & fees
29 May - 30 May
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)
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 AED 400
AED 842 total
includes taxes & fees
16 Jun - 17 Jun
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 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 AED 551
AED 972 total
includes taxes & fees
3 Jun - 4 Jun
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)
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)
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)
Hot Tub | Great Location |Patio| Grill | Tempurpedic Beds
Hot Tub | Great Location |Patio| Grill | Tempurpedic Beds
10.0 out of 10, Exceptional, (37)
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)
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)
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 AED 463
AED 510 total
includes taxes & fees
6 Jun - 7 Jun
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 AED 439
AED 847 total
includes taxes & fees
12 Jun - 13 Jun
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 AED 496
AED 830 total
includes taxes & fees
25 Jun - 26 Jun
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.
Recent reviews of Winchester hotelsExpedia verified reviews
5/5 Excellent
"The front desk staff was tremendous."
A verified traveler from Colorado Springs stayed at Hyatt Regency Lexington
Posted 19 hours ago
Top Vacation Homes in Other Destinations
More Accommodation Types in Winchester
- Cabin Rentals in Winchester (161)
- Apartments in Winchester (114)
- Condo Rentals in Winchester (48)
- Cottages in Winchester (30)
- RV Parks in Winchester (13)
- Motels in Winchester (13)
- Farmstay in Winchester (10)
- 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)