Vacation Homes in Winchester, IN
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Top 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

3-bedroom vacation home 9 minutes from Ball State University in the country.

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

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Find the Best Vacation Homes in Winchester
Why book a vacation home in Winchester?
Vacation homes in Winchester make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.
How much is a vacation home in Winchester?
Private Winchester rental homes range between - per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.
What are the cancellation and flexibility options on Travelocity?
To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.
What amenities should I look out for in a vacation home?
There are some exciting amenities available in Winchester vacation home rentals. You might look for Winchester rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room.
Vacation rentals in Winchester offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.
When is the best time to rent a vacation home in Winchester?
You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.
Why book a vacation home with Travelocity?
Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Winchester. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Winchester hotels and vacation homes that best suit your stay. We also have deals for flights, and Winchester car rentals. You’ll save even more when you bundle your items into a Winchester vacation package!
How many vacation homes are available to book in Winchester?
There are 52 rental homes in Winchester. Enter your travel dates to check availability.
How do I find the best price for a vacation home in Winchester?
Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.
Winchester Vacation Homes essential information
Accommodation | 52 Vacation Homes |
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Lowest Price | |
Highest Price | |
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, 3-bedroom vacation home 9 minutes from Ball State University in the country., Charming 3-bedroom house in tranquil Greenville with WiFi, AC, and game room. , Boho Bungalow off Main-one block from Lovely Park |