Vacation Homes in Winchester
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Featured Vacation Homes in Winchester
Horse Country 2 - Sleeping For 12 - Beautiful Outdoor Space - 3 Bedrooms + Loft
2 Bed/2 Bath Home in Andover area. Premier Host with 250+ 5-Star Reviews!
Newly renovated Historic House within walking distance to UK.
Lexington’s Premier Cul De Sac Townhome 2BR, 2.5BA, 1100 sqft
Robin's Nest luxury cabin, Red River Gorge
Hamburg Haven / Garage /🔥 Pit / 7mi to Rupp / WiFi
Experience the Grand Getaway: Centrally Located Luxury
Barn! 2-Hole Golf Course, BBall, Wiffleball, Soccer, Theater, Arcade, 2 Hot Tubs
Home with Fire-pit - Sleeps 8. Walk 1 Block to EKU & Downtown, 3 Miles to I-75
5 Star Location | Walk to Downtown | Patio | Fire Pit
WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!
Top trending hotels in Winchester
The Manchester
Vacation Rentals in Winchester
What kind of vacation do you want in Winchester? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation rental is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Winchester that will speak to you.
Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Winchester, including luxury vacation rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.
Take a look at what we have on offer. You’ll find rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.
Winchester Vacation Homes essential information
Accommodation | 352 Vacation Homes |
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Lowest Price | CA $83 |
Highest Price | CA $526 |
Popular accommodation | Horse Country 2 - Sleeping For 12 - Beautiful Outdoor Space - 3 Bedrooms + Loft, 2 Bed/2 Bath Home in Andover area. Premier Host with 250+ 5-Star Reviews!, Newly renovated Historic House within walking distance to UK., Lexington’s Premier Cul De Sac Townhome 2BR, 2.5BA, 1100 sqft, Robin's Nest luxury cabin, Red River Gorge, Hamburg Haven / Garage /🔥 Pit / 7mi to Rupp / WiFi, Experience the Grand Getaway: Centrally Located Luxury, Barn! 2-Hole Golf Course, BBall, Wiffleball, Soccer, Theater, Arcade, 2 Hot Tubs, Home with Fire-pit - Sleeps 8. Walk 1 Block to EKU & Downtown, 3 Miles to I-75, 5 Star Location | Walk to Downtown | Patio | Fire Pit, WiFi, Hot Tub, Pets, Prime Location in Red River Gorge!, NEW! East Suite- Southern Charm in Georgetown Kentucky-Bleubird Studio + Suites |