Save hundreds with a vacation home rental from Tripping.com and forget the hotel room. For the ultimate getaway, Winchester offers 414 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Winchester start at an average price of $216 a night with long-term rentals averaging $4050 a month.These vacation rentals offer a range of amenities, so you’ll feel right at home. For those looking to stay in a corporate rental, 300 of Winchester’s rentals offer high speed WiFi Internet so you can easily keep in touch with your company or team. Go for a swim at one of the 186 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 279 vacation home rentals.Traveling with your dog or cat? Choose from 119 pet-friendly rentals in Winchester that allow you to bring your extended family along.Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your pets. Many properties allow you to book directly online, so once you find that perfect vacation rental, you’ll be all set to go!Search properties from 7 vacation rental sites in Winchester where the top providers in that area are HomeAway, Expedia, and Booking.com. There are 96 HomeAway rentals, 85 Expedia short term rentals and 81 Booking.com vacation rentals.