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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Winchester vacation rentals

Dining

1. Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Jacksonville
10.0 out of 10, Exceptional, (23 reviews)
"Really enjoyed our stay. The place was very clean and bed really comfortable "
United States
David W.
$119 nightly
The price is $126
Sep 7 - Sep 8
Total with taxes and fees
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Exterior

2. Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Jacksonville
10.0 out of 10, Exceptional, (17 reviews)
"The place was really neat and the host was incredibly friendly"
United States
Dylan
$149 nightly
The price is $158
Sep 15 - Sep 16
Total with taxes and fees
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Exterior

3. Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee

Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee
Murrayville
9.8 out of 10, Exceptional, (69 reviews)
"Kevin was a great host. Responsive when I had issues with the lock. Great homemade cookies. "
United States
Anonymous traveler
$131 nightly
The price is $139
Aug 31 - Sep 1
Total with taxes and fees
Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee
Dining

4. Peace on the Prairie — Quiet Nature Retreat on 24 Acres

Peace on the Prairie — Quiet Nature Retreat on 24 Acres
Murrayville
10.0 out of 10, Exceptional, (31 reviews)
"Exactly as described, wonderful experience."
United States
Petraborg P.
$115 nightly
The price is $121
Sep 8 - Sep 9
Total with taxes and fees
Peace on the Prairie — Quiet Nature Retreat on 24 Acres
Property grounds

5. 3-bedroom country home in Pike Co Il with AC and heat

3-bedroom country home in Pike Co Il with AC and heat
Chambersburg
10.0 out of 10, Exceptional, (1 review)
"Would go back here many times over again. Was exactly what we needed."
United States
Jake O.
$187 nightly
The price is $198
Aug 30 - Aug 31
Total with taxes and fees
3-bedroom country home in Pike Co Il with AC and heat
Room

6. The Farmhouse Loft "Greene County's Guesthouse"

The Farmhouse Loft "Greene County's Guesthouse"
Carrollton
9.8 out of 10, Exceptional, (62 reviews)
"Stayed at the Farmhouse Loft for a local wedding. It met all our expectations. Great location on the town square. Will definitely stay there again "
United States
Gregory D.
$155 nightly
The price is $164
Aug 30 - Aug 31
Total with taxes and fees
The Farmhouse Loft "Greene County's Guesthouse"
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

Monroe Street Suites

Monroe Street Suites

10/10 Excellent
"Good"
Braiden 4-night trip
Posted 10 hours ago
Monroe Street Suites

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 $121 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.

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?

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!: Visitors like this Winchester vacation home rental. It offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.