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Winchester Cottage Rentals & Holiday Homes
Find the best cottages in Winchester - We found 36 exact matches
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About Winchester Cottage Rentals on PickleTrip
Searching for cottages to rent near Winchester? PickleTrip™ features more than 36 cottages that are perfect for your next pickleball getaway. Plan your ultimate holiday and discover luxury cottage rentals that are a few miles away from the lake or beach and have access to private courts or nearby facilities. These cottage rentals in Winchester have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. PickleTrip™’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Winchester.
Are you planning to travel to the lakeside, beach, or mountain area? PickleTrip™’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.
PickleTrip™ boasts of 36 holiday cottages and places to stay in Winchester. The site provides unique Airbnb, VRBO, pickleball-ready cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday — all fitting within your budget.
Frequently Asked Questions About Winchester Rental Cottages
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 Cottage Rentals in Winchester:
- PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
- COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
- Modern Farmhouse, Central Pike Co. IL, Scenic views, Spacious gathering room
- Peaceful studio retreat surrounded by prairie, wildlife, and open skies.
- Home with great location
- Villa DeWolf
- Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, ILn
- Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonvillen
- Beautiful secluded lodge with a breathtaking view!
- Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
- PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
- Best Western Jacksonville Inn
- Villa DeWolf
- Modern Farmhouse, Central Pike Co. IL, Scenic views, Spacious gathering room
See all pet-friendly vacation rentals in Winchester on PickleTrip
