Winchester Vacation Rentals

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Tonight
Oct 15 - Oct 16
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Oct 16 - Oct 17
This weekend
Oct 17 - Oct 19
Next weekend
Oct 24 - Oct 26

Vacation Rentals in Winchester

Dining
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
10.0 out of 10, Exceptional, (14)
"Wonderfully peaceful with a little wildlife added for fun. "
$119 nightly
The price is $126
Oct 16 - Oct 17
Total with taxes and fees
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Fridge, microwave, oven, stovetop
Peaceful studio retreat surrounded by prairie, wildlife, and open skies.
Peaceful studio retreat surrounded by prairie, wildlife, and open skies.
10.0 out of 10, Exceptional, (25)
"We had a great stay. The environment is just cuddling. "
$98 nightly
The price is $104
Oct 16 - Oct 17
Total with taxes and fees
Peaceful studio retreat surrounded by prairie, wildlife, and open skies.
Terrace/patio
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
9.8 out of 10, Exceptional, (80)
"We had the best time staying here. My family of 20 stayed for 3 days and this place was perfect for our trip. The house was large enough to accommodate everyone comfortably and we had everything we needed. The pool area is awesome - everyone had an amazing time from the 2 year old to my 70 year old dad. A great place for kids. Communication was great and the owners were friendly and very helpful. Hope to come back again some day! "
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Exterior
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
2.0 star property
$330 nightly
The price is $350
Oct 16 - Oct 17
Total with taxes and fees
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland
Dining
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
10.0 out of 10, Exceptional, (58)
"Our stay at the Llama Fun Guest House was incredible! We got to tour the grounds and meet the llamas and then relaxed in the very spacious and clean house! Kris and Terry were very welcoming and we felt right at home there. We will definitely be back!"
$200 nightly
The price is $212
Oct 16 - Oct 17
Total with taxes and fees
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Fridge, microwave, oven, stovetop
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
9.8 out of 10, Exceptional, (57)
"Exactly what we needed. Peaceful, secluded, and relaxing! The trails are an added bonus. The respect for nature, pets, and people spoke to us, which are evident in the aesthetic of the property. We come to Jacksonville often and will definitely be back!"
$96 nightly
The price is $101
Nov 12 - Nov 13
Total with taxes and fees
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
Interior
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
10.0 out of 10, Exceptional, (8)
"The cabin is perfect for creating a relaxing atmosphere. We always like our stay there."
$149 nightly
The price is $158
Oct 16 - Oct 17
Total with taxes and fees
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Exterior
Home with great location
Home with great location
10.0 out of 10, Exceptional, (23)
"Great stay for our family - thank you!"
Home with great location
Interior
Country Retreat in the heart of Pike County Illinois
Country Retreat in the heart of Pike County Illinois
Country Retreat in the heart of Pike County Illinois
Fridge, microwave, oven, stovetop
The Farmhouse Loft "Greene County's Guesthouse"
The Farmhouse Loft "Greene County's Guesthouse"
9.8 out of 10, Exceptional, (59)
"Very cute place!!!"
$155 nightly
The price is $164
Oct 19 - Oct 20
Total with taxes and fees
The Farmhouse Loft "Greene County's Guesthouse"
Microwave, oven, stovetop
Dave’s River House
Dave’s River House
$225 nightly
The price is $227
Oct 22 - Oct 23
Total with taxes and fees
Dave’s River House
House (4 Bedrooms) | Interior
Idyllic Mt Sterling Retreat w/ Private Lake!
Idyllic Mt Sterling Retreat w/ Private Lake!
2.0 star property
Idyllic Mt Sterling Retreat w/ Private Lake!
House (1 Bedroom) | Interior
Exotic Animal Farm Stay in Illinois: Tour, Explore
Exotic Animal Farm Stay in Illinois: Tour, Explore
3.0 star property
Exotic Animal Farm Stay in Illinois: Tour, Explore
Property grounds
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
$156 nightly
The price is $165
Oct 25 - Oct 26
Total with taxes and fees
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area
BBQ/picnic area
West Central Lodging
West Central Lodging
2.5 star property
10.0 out of 10, Exceptional, (1)
"We had a wonderful time - very quiet country location, the manager is friendly but not invasive. First time I have heard a whippoorwill sing in many years. "
West Central Lodging
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

Best Western Jacksonville Inn

Best Western Jacksonville Inn

10/10 Excellent
"Terrific."
Don 1-night trip
Posted 2 days ago
Best Western Jacksonville Inn

Find out more about Winchester

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 $101 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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Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, you can find vacation rentals near top points of interest in Winchester, or you can select a secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals that Winchester has to offer?

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: Visitors like this Winchester vacation home rental. It is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

What’s there to see and do in Winchester?

While you're exploring the area, Lake Jacksonville and Jacksonville Community Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Morgan County Fairgrounds and Illinois College.

What’s a vacation rental in Winchester like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Winchester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family getaway.