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 prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 424 Vacation Homes in Winchester with updated reviews, rates, and availability.

Luxurious 1-bedroom with Free Parking
Luxurious 1-bedroom with Free Parking
9.8 out of 10, Exceptional, (35)
The price is AED 364
AED 955 total
includes taxes & fees
8 Jun - 9 Jun

Bluegrass Oasis - Entire house,12 guests, 5mi to KHP
Bluegrass Oasis - Entire house,12 guests, 5mi to KHP
9.8 out of 10, Exceptional, (19)

Hot Tub/Playground/12 min to Horse Park/30min Ark
Hot Tub/Playground/12 min to Horse Park/30min Ark
10.0 out of 10, Exceptional, (17)
The price is AED 595
AED 1,425 total
includes taxes & fees
13 May - 14 May

Welcome to “The Spot” - North Limestone/Downtown!
Welcome to “The Spot” - North Limestone/Downtown!
10.0 out of 10, Exceptional, (30)

3 BR 2 bath 5 beds! sleeps 8. Pool, hot tub oasis in LEX
3 BR 2 bath 5 beds! sleeps 8. Pool, hot tub oasis in LEX
9.4 out of 10, Exceptional, (10)

Cali king beds. Best of Nicholasville! Koi pond relaxing backyard. 3 bed 2 bath
Cali king beds. Best of Nicholasville! Koi pond relaxing backyard. 3 bed 2 bath
10.0 out of 10, Exceptional, (94)

Modern 2bd 2ba- Near I-75, Free WiFi, No Steps
Modern 2bd 2ba- Near I-75, Free WiFi, No Steps
9.8 out of 10, Exceptional, (71)
The price is AED 437
AED 806 total
includes taxes & fees
13 May - 14 May

Spacious house minutes from the Horse Park
Spacious house minutes from the Horse Park
9.2 out of 10, Wonderful, (23)
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Winchester

Natural Bridge State Resort Park
Natural Bridge State Resort Park
8.6 out of 10, Excellent, (1552)
The price is AED 463
AED 510 total
includes taxes & fees
13 May - 14 May

Tranquil Getaway in the Woods ~ Sunset Ridge
Tranquil Getaway in the Woods ~ Sunset Ridge
9.8 out of 10, Exceptional, (55)
The price is AED 386
AED 547 total
includes taxes & fees
13 May - 14 May

Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
Hot Tub & WiFi - Small Family Cabin - Throw'n Shade - Wooded Retreat near Red River Gorge, Kentucky!
9.4 out of 10, Exceptional, (68)
The price is AED 397
AED 813 total
includes taxes & fees
14 May - 15 May
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 hotels
Recent reviews of Winchester hotels

Quality Inn Lexington -Horse Park
5/5 Excellent
"Just the place for that day "
A verified traveler stayed at Quality Inn Lexington -Horse Park
Posted 19 hours ago