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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, (33)
The price is SAR 372
SAR 1,018 total
includes taxes & fees
20 Apr - 21 Apr

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, (14)
The price is SAR 681
SAR 1,499 total
includes taxes & fees
29 Apr - 30 Apr

Welcome to “The Spot” - North Limestone/Downtown!
Welcome to “The Spot” - North Limestone/Downtown!
10.0 out of 10, Exceptional, (29)

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
9.8 out of 10, Exceptional, (9)

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, (92)

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, (69)
The price is SAR 447
SAR 844 total
includes taxes & fees
21 Apr - 22 Apr

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.
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Other property types in Winchester

Natural Bridge State Resort Park
Natural Bridge State Resort Park
8.6 out of 10, Excellent, (1526)
The price is SAR 435
SAR 480 total
includes taxes & fees
29 Apr - 30 Apr

Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
Hot Tub, WiFi & Pet-Friendly - Secluded Family Getaway - Pilot Point - Red River Gorge, Kentucky!
9.6 out of 10, Exceptional, (141)
The price is SAR 425
SAR 864 total
includes taxes & fees
11 May - 12 May

Tranquil Getaway in the Woods ~ Sunset Ridge
Tranquil Getaway in the Woods ~ Sunset Ridge
9.8 out of 10, Exceptional, (53)
The price is SAR 394
SAR 559 total
includes taxes & fees
21 Apr - 22 Apr
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

Days Inn Lexington SE/Hamburg
5/5 Excellent
"Staff is wonderful! Clean pet friendly place close to both interstate and town for shopping. Wonderful place to stay!! "
A verified traveler stayed at Days Inn Lexington SE/Hamburg
Posted 12 hours ago