Winchester Vacation Rentals
Vacation Rentals in Winchester
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Home with great location
The Farmhouse Loft "Greene County's Guesthouse"
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees
Idyllic Mt Sterling Retreat w/ Private Lake!
Art Themed Loft Apartment in Jacksonville
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
5 Bedroom Lodge in Illinois
Cozy 3 bedroom family friendly home in pike county IL
Cozy cabin overlooking an exotic animal farm!
River Cottage Along the Illinois River.
Idyllic Mt Sterling Retreat w/ Private Lake!
West Central Lodging
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Other types of properties in Winchester you may be interested in
Best Western Jacksonville Inn
Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel
Sleep Inn & Suites
Everything you need to know about Winchester vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Winchester vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!
How to find incredible deals on Winchester rentals
At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
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