What are the top vacation rentals in Winchester?

There are a lot of options in Winchester. If you plan on staying in the Winchester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winchester: <a href="/property/indoor-gymnasium-seasonal-pool-7-bedroom-sleeps-30/HA-3212020956" class="class="static-page-link"">Indoor Gymnasium, Seasonal Pool, 7 Bedroom, Sleeps 30</a> <a href="/property/creek-house-on-burton-farm/HA-1214990790" class="class="static-page-link"">Creek House On Burton Farm</a> <a href="/property/5-min-walk-to-bsu-campus-quiet-neighborhood/HA-3212918752" class="class="static-page-link"">5 min walk to BSU Campus - Quiet Neighborhood</a> <a href="/property/recently-remodeled-colonial-style-home-with-room-for-the-whole-family/HA-3213159819" class="class="static-page-link"">Recently remodeled Colonial-style home with room for the whole family!</a> <a href="/property/entire-home-in-cambridge-city/HA-3213502983" class="class="static-page-link"">Entire Home in Cambridge City</a> <a href="/property/downtown-new-castle-indiana-condo-available-for-short-term-and-long-term-stays/HA-3212391153" class="class="static-page-link"">Downtown New Castle Indiana Condo Available for short-term and long-term stays.</a> <a href="/property/guest-favorite-near-ball-state-iu-hospital-december-specials-top-rated/HA-3213433779" class="class="static-page-link"">Guest Favorite Near Ball State &amp; IU Hospital &amp; December Specials Top-Rated</a> <a href="/property/settle-in-at-the-petite-retreat/HA-3212274324" class="class="static-page-link"">Settle in at the Petite Retreat.</a> <a href="/property/pet-friendly-greenville-home-w-private-yard/HA-1219710748" class="class="static-page-link"">Pet-Friendly Greenville Home w/Private Yard</a> <a href="/property/3-bedroom-house-in-fort-recovery/HA-3212601775" class="class="static-page-link"">3 Bedroom House in Fort Recovery</a>

How many vacation rentals have private pools in Winchester?

There are 14 vacation rentals with private pools near Winchester. Top-rated Themeparkhotels homes that have access to a swimming pool include: <a href="/property/cozy-cabin-with-fireplace-hot-tub-hiking-trails/HA-3213223546" class="class="static-page-link"">Cozy Cabin with fireplace, hot tub &amp; hiking trails</a> <a href="/property/fairfield-inn-by-marriott-richmond/BC-191912" class="class="static-page-link"">Fairfield Inn by Marriott Richmond</a> <a href="/property/stunning-home-with-in-ground-pool-hot-tub-bocce-court-gourmet-granite-kitchen/HA-3213598407" class="class="static-page-link"">Stunning home with in ground pool, hot tub, bocce court, gourmet granite kitchen</a> <a href="/property/harmony-hideaway-over-4000-sqft-5-mins-to-bsu-iu-games-rooms-and-summer-pool/HA-3213795515" class="class="static-page-link"">Harmony Hideaway Over 4000 sqft, 5 mins to BSU &amp; IU, Games Rooms and Summer Pool</a>

Which vacation homes in Winchester are best for families?

If you are looking for a family-friendly vacation home in Winchester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winchester: <a href="/property/family-friendly-home-beautiful-fenced-in-yard-short-walk-to-ball-state-campus/HA-3214752899" class="class="static-page-link"">Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus</a> <a href="/property/cozy-muncie-home-near-downtown/BC-12187003" class="class="static-page-link"">Cozy Muncie Home Near Downtown</a> <a href="/property/hampton-inn-suites-muncie/EP-2041430" class="class="static-page-link"">Hampton Inn &amp; Suites Muncie</a>

How many vacation rentals are available in Winchester?

Currently, the total number of properties listed in 2026 is over 254 in the Winchester area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Winchester.