Winchester Vacation Rentals

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Vacation Rentals in Winchester

Property grounds
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
9.8 out of 10, Exceptional, (43)
"The place is really comfortable, and the trails and nature around are perfect for exploring, especially with my dog. It was so easy to relax and just enjoy the quiet. Great spot if you want a break from it all and don’t want to worry about leaving your pet behind. Definitely recommend!"
The price is CA $127
CA $162 total
includes taxes & fees
May 28 - May 29
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
Property grounds
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
9.8 out of 10, Exceptional, (66)
"Beautiful, spacious and delightful"
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
2 bedrooms, iron/ironing board, WiFi, bed sheets
Art Themed Loft Apartment in Jacksonville
9.6 out of 10, Exceptional, (4)
"So cutely decorated! Much bigger than expected. Would definitely stay here again."
The price is CA $130
CA $205 total
includes taxes & fees
May 27 - May 28
Art Themed Loft Apartment in Jacksonville
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Fridge, microwave, oven, stovetop
The Farmhouse Loft "Greene County's Guesthouse"
9.8 out of 10, Exceptional, (45)
"My daughter and I came up to explore our geneology and visit local cemeteries. I wish I had known how steep the stairs were, but we made it. We would chiise a different venue next time."
The price is CA $117
CA $213 total
includes taxes & fees
Jun 4 - Jun 5
The Farmhouse Loft "Greene County's Guesthouse"
Exterior
Home with great location
10.0 out of 10, Exceptional, (9)
"Loved the property. Perfect place for our family while attending our daughter’s graduation. Conveniently located. House is so quaint. Highly recommend it."
Home with great location
Fridge, microwave, oven, stovetop
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees
10.0 out of 10, Exceptional, (19)
"Great spot for our weekend away!"
The price is CA $123
CA $158 total
includes taxes & fees
May 26 - May 27
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees
Interior
Idyllic Mt Sterling Retreat w/ Private Lake!
10.0 out of 10, Exceptional, (3)
"Comfortable and well-equipped home, with more than enough towels. Under-advertised as has 2 1/2 baths, and use of the boathouse. Loved swimming and jumping off the dock, fishing, and just trolling around the lake with the two boats with trolling motors, and the peddle boat. Very wide mowed path around the lake and other trails. Also had marshmallow forks for the s’mores around the campfire. Enjoyed the rocking bench at the end of the dock, especially in the early morning and for watching...
Idyllic Mt Sterling Retreat w/ Private Lake!
Fridge, microwave, oven, stovetop
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
10.0 out of 10, Exceptional, (43)
"Our family had a great stay in IL. The house was excellent and the llamas were an added entertainment . Would definitely come back to stay!!"
The price is CA $272
CA $308 total
includes taxes & fees
Jun 7 - Jun 8
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Pool
5 Bedroom Lodge in Illinois
9.8 out of 10, Exceptional, (29)
"Wonderful property, great hosts. We will be back."
5 Bedroom Lodge in Illinois
Exterior
Cozy 3 bedroom family friendly home in pike county IL
Cozy 3 bedroom family friendly home in pike county IL
Terrace/patio
Cozy cabin overlooking an exotic animal farm!
The price is CA $240
CA $271 total
includes taxes & fees
May 26 - May 27
Cozy cabin overlooking an exotic animal farm!
Exterior
River Cottage Along the Illinois River.
The price is CA $96
CA $129 total
includes taxes & fees
Jun 13 - Jun 14
River Cottage Along the Illinois River.
Interior
Idyllic Mt Sterling Retreat w/ Private Lake!
2.0 star property
Idyllic Mt Sterling Retreat w/ Private Lake!
BBQ/picnic area
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
Exterior
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
The price is CA $122
CA $157 total
includes taxes & fees
May 28 - May 29
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Interior
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
The price is CA $177
CA $215 total
includes taxes & fees
May 26 - May 27
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Don't see what you're looking for?
See all available properties in Winchester
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.

Other types of properties in Winchester you may be interested in

Indoor pool
Best Western Jacksonville Inn
2.5 star property
8.4 out of 10, Very good, (539)
"Nous avons été super bien reçus, la chambre est correct, aurait grand besoin d'un rafraîchissement, mais c'est propre et confortable "
The price is CA $110
CA $125 total
includes taxes & fees
Jun 2 - Jun 3
Best Western Jacksonville Inn
Exterior
Sleep Inn & Suites
2.5 star property
9.4 out of 10, Exceptional, (382)
"Ok for the price. More then expected"
The price is CA $122
CA $135 total
includes taxes & fees
Jun 2 - Jun 3
Sleep Inn & Suites
Exterior
Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel
2.5 star property
7.8 out of 10, Good, (338)
"We had a major issue with my mother's room and the manager took action and took care of it. We appreciate it!"
The price is CA $110
CA $122 total
includes taxes & fees
Jun 9 - Jun 10
Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel
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.

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester vacation rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard 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?

Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.: Visitors like this Winchester vacation home rental. It is located in a rural location and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a spa tub and a selection of books.

What’s there to see and do in Winchester?

While you're exploring the area, Lake Jacksonville and King 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.

Recent reviews of Winchester properties
Expedia verified reviews

Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.

Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.

5/5 Excellent
Highly Recommend
"The place is really comfortable, and the trails and nature around are perfect for exploring, especially with my dog. It was so easy to relax and just enjoy the quiet. Great spot if you want a break from it all and don’t want to worry about leaving your pet behind. Definitely recommend!"
A verified traveller stayed at Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
Posted 5 days ago
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.