Search Apartments in Winchester

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

Compare 2 Apartments in Winchester with updated reviews, rates, and availability.

The Farmhouse Loft "Greene County's Guesthouse"
Fridge, microwave, oven, stovetop

The Farmhouse Loft "Greene County's Guesthouse"

9.8 out of 10, Exceptional, (53)
"We had an overnight stay during a very long roadtrip, the loft was perfect and we were able to have a very relaxing night after eating some of the best pizza I have ever had, highly recommend the place just a few hundred feet away. Communication with owners was perfect."
The price is AED 312
AED 569 total
includes taxes & fees
14 Apr - 15 Apr
The Farmhouse Loft "Greene County's Guesthouse"
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees
Fridge, microwave, oven, stovetop

Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees

10.0 out of 10, Exceptional, (22)
"We had a great stay. The environment is just cuddling. "
The price is AED 349
AED 443 total
includes taxes & fees
15 Apr - 16 Apr
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winchester

The Farmhouse Loft "Greene County's Guesthouse"
Fridge, microwave, oven, stovetop

The Farmhouse Loft "Greene County's Guesthouse"

9.8 out of 10, Exceptional, (53)
"We had an overnight stay during a very long roadtrip, the loft was perfect and we were able to have a very relaxing night after eating some of the best pizza I have ever had, highly recommend the place just a few hundred feet away. Communication with owners was perfect."
The price is AED 312
AED 569 total
includes taxes & fees
14 Apr - 15 Apr
The Farmhouse Loft "Greene County's Guesthouse"
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Property grounds

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

10.0 out of 10, Exceptional, (4)
"This was a last minute booking for a softball tournament and a great find. Its 10 minutes from the future champions complex in Jacksonville and honestly a great find. No giggling girls yelling up and down the hallways just peaceful rest! The hosts did not forget a thing Thank you for a great sray."
The price is AED 327
AED 421 total
includes taxes & fees
14 Apr - 15 Apr
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees
Fridge, microwave, oven, stovetop

Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees

10.0 out of 10, Exceptional, (22)
"We had a great stay. The environment is just cuddling. "
The price is AED 349
AED 443 total
includes taxes & fees
15 Apr - 16 Apr
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees
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.

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You might not have many choices centrally in Winchester, but Expedia can help you search for accommodations in the area with similar amenities to an apartment. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment such as a kitchen. Even filter by similar properties such as vacation homes, condos, or cabins.
Why choose apartments instead of traditional hotels?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and is often more spacious than a traditional hotel room. Apartments are a good option for couples who want a more local feel, and also for families wanting the conveniences of home.
What's the top apartment for my stay in Winchester?
Here are some of the more popular apartments in the area to choose from: The Farmhouse Loft “Greene County’s Guesthouse”: Located in Carrollton, 22.8 mi/36.6 km from the heart of Winchester. Includes Smart TVs. Access to a fitness center is available on site. Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees: Located 16.3 mi/26.3 km away in Murrayville. Free WiFi, sofa beds, and Smart TVs are included.
What will the weather be like during my trip to Winchester?
Weather is only one factor, but it can really affect your travel plans, especially when you’re planning an extended stay in Winchester. The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 35°F. Average annual precipitation for Winchester is 49 inches.
What are the must-see places to visit 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. Morgan County Fairgrounds and Illinois College are a couple of places you’ll find in the larger area.