Winchester Vacation Rentals
Get more for your budget and save up to 50% off select Secret Bargain hotels
Get even more value with CheapTickets Price Guarantee!
Change your flight without a fee on select flights
Vacation Rentals in Winchester
URBAN GETAWAY - .6 Downtown Maysville/Entire House
The price is $121 per night
$121
includes taxes & fees
$109 per night
Nov 7 - Nov 8
Located in Maysville, this vacation home is on a river, within a 15-minute walk of Ohio River and Russell Theatre.
Kitchen
Washer
THIS IS IT!! Large Private Home, 8 Acres Borders Forest; Includes All Amenities!
When you stay at this vacation home in Peebles, you'll be in the mountains and steps from Brush Creek State Forest.
Kitchen
Washer
LAKE HOUSE ON ROCKY FORK!
When you stay at this vacation home in Hillsboro, you'll be on a lake, within a 5-minute drive of Rocky Fork Lake and Rocky Fork State Park.
Kitchen
Pet friendly
Beautiful Rocky Fork 2BR Cozy Cottage
When you stay at this vacation home in Hillsboro, you'll be on a lake, within a 5-minute drive of Rocky Fork State Park and Rocky Fork Lake State Park.
Kitchen
Washer
McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events
Located in Williamsburg, this vacation home is a 3-minute drive from Williamsburg Branch Public Library and 7 minutes from East Fork State Park.
Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats
Located in Hamersville, this vacation home is on a lake, within a 15-minute drive of Harmony Hill Vineyard and East Fork State Park.
Peaceful Country Retreat 20 acres Private Pond
With a stay at this vacation home in Sardinia, you'll be 31.7 mi (51.1 km) from EastGate Mall and 15.4 mi (24.8 km) from Meranda-Nixon Winery.
The Manor at Maysville Golf Course View
The price is $693 per night
$693
includes taxes & fees
$623 per night
Nov 15 - Nov 16
When you stay at this vacation home in Maysville, you'll be next to a golf course, within a 5-minute drive of National Underground Railroad Museum and Kentucky Gateway Museum Center.
Kitchen
Washer
Unique stay, hot tub, secluded
The price is $241 per night
$241
includes taxes & fees
$238 per night
Nov 20 - Nov 21
A stay at this vacation home places you in the heart of Peebles, and within a 15-minute drive of Adams Lake State Park.
Hot Tub
Kitchen
Rustic Lodge with private cabins / 6 person hot tub and camp fire
Located in Hillsboro, this vacation home is on a lake, within a 5-minute drive of Highland District Hospital and Southern State Community College.
Hot Tub
Kitchen
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 Rentals essential information
Accommodation | 37 Vacation Rentals |
|---|---|
Lowest Price | $121 |
Highest Price | $693 |
Popular accommodation | URBAN GETAWAY - .6 Downtown Maysville/Entire House, THIS IS IT!! Large Private Home, 8 Acres Borders Forest; Includes All Amenities!, LAKE HOUSE ON ROCKY FORK!, Beautiful Rocky Fork 2BR Cozy Cottage, McKeever Mansion-9,000 sq ft. Perfect for corporate, families, or special events, Quiet Country Home sleeps 22 people, perfect for Reunions, Teams, Retreats, Peaceful Country Retreat 20 acres Private Pond, The Manor at Maysville Golf Course View, Unique stay, hot tub, secluded, Rustic Lodge with private cabins / 6 person hot tub and camp fire, Hillsboro Hideaway w/ Private Hot Tub & Bunkhouse!, Beautifully renovated 3BR house w/lake views |