Vacation Homes in Winchester
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Featured Vacation Homes in Winchester

Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

Cardinal Cottage - 2 bedroom cozy home

5 min walk to BSU Campus - Quiet Neighborhood

May/June Specials-Guest favorite! Near IU Health Hospital &Ball State University

Quaint Economy Retreat w/ Patio & Spacious Yard!

Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!

Westcott Mansion with Pickleball Court & Huge Gazebo

The Red House

Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room.

Boho Bungalow off Main-one block from Lovely Park
Top trending hotels in Winchester

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
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 | 52 Vacation Homes |
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Popular accommodation | Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting., Cardinal Cottage - 2 bedroom cozy home, 5 min walk to BSU Campus - Quiet Neighborhood, May/June Specials-Guest favorite! Near IU Health Hospital &Ball State University, Quaint Economy Retreat w/ Patio & Spacious Yard!, Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy, Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!, Westcott Mansion with Pickleball Court & Huge Gazebo, The Red House, Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room. , Boho Bungalow off Main-one block from Lovely Park, 3 bedroom 1.5 bath house. Walkable to BSU and many restaurants, ping pong table |