Winchester Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
23 Oct - 24 Oct
Tomorrow
24 Oct - 25 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

Holiday 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. "
United States
Peggy M.
The price is HK$769
HK$980 total
includes taxes & fees
27 Oct - 28 Oct
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. "
United States
Anonymous traveller
The price is HK$863
HK$1,079 total
includes taxes & fees
21 Nov - 22 Nov
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! "
United States
Alison B.
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
The price is HK$1,951
HK$2,735 total
includes taxes & fees
25 Oct - 26 Oct
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)
"We enjoyed our stay at this beautiful country home. "
United States
Andrea C.
The price is HK$1,392
HK$1,689 total
includes taxes & fees
24 Oct - 25 Oct
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, (58)
"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!"
United States
Laura
The price is HK$653
HK$857 total
includes taxes & fees
12 Nov - 13 Nov
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."
United States
James Z.
The price is HK$1,002
HK$1,227 total
includes taxes & fees
27 Oct - 28 Oct
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!"
United States
Marty S.
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, (60)
"Very cute place!!!"
United States
Debbie S.
The price is HK$661
HK$1,277 total
includes taxes & fees
2 Nov - 3 Nov
The Farmhouse Loft "Greene County's Guesthouse"
Microwave, oven, stovetop
Dave’s River House
Dave’s River House
Dave’s River House
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!
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
The price is HK$902
HK$1,286 total
includes taxes & fees
25 Oct - 26 Oct
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. "
United States
Anonymous traveller
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Sleep Inn & Suites

Sleep Inn & Suites

10/10 Excellent
"Very clean and comfortable, quiet,and really good breakfast."
Sandy 1-night trip
Posted 3 days ago
Sleep Inn & Suites

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

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

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: This holiday home rental outside of Winchester is located in a rural location, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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 wider area, you’ll find Morgan County Fairgrounds and Illinois College.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family trip.