Compare and book 4 Star hotels in Winchester, Illinois

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on Winchester 4 Star Hotels

Tonight
30 Aug - 31 Aug
Tomorrow
31 Aug - 1 Sep
Next weekend
5 Sep - 7 Sep
In two weeks
12 Sep - 14 Sep

Top Winchester 4 Star Hotels

Villa DeWolf
Front of property

Villa DeWolf

4.0 star property
10.0 out of 10, Exceptional, (10)
"If you want the kindest hospitality, delicious breakfast and a memorable experience at a gorgeous historical home instead of a generic hotel, you must stay here!"
Villa DeWolf
Blessings on State Bed & Breakfast
Property grounds

Blessings on State Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (55)
"Excellent property with welcoming staff and cozy, well-appointed rooms. "
Blessings on State Bed & Breakfast
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

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Winchester?
To lock in a 4-star hotel in Winchester that matches your budget, make use of Expedia's sort and search filters. Take a look at what's available during your holiday dates and use our pricing filter to set your maximum rate. You can also sort your results by the most wallet-friendly property first.

  • Search for the lowest price

What's the difference between 5-star and 4-star hotels in Winchester?
Offering an inviting traveller experience and upscale décor, 4-star hotels are a terrific option for your Winchester escape. These kinds of accommodation generally come with lots of handy amenities that make it a breeze to unpack and relax — think pillowtop mattresses, gyms and restaurants. Or live the high life at a 5-star hotel designed to spoil you with high-end perks and amenities. 24-hour front desk, complimentary toiletries and world-class dining are typically featured at these deluxe properties.
Does Winchester have any 4-star all-inclusive resorts?
Enjoy a stress-free holiday experience where just about everything is included in the one upfront rate by using our "All inclusive" filter. Staying within budget is a cinch when your meals, accommodation and activities are already taken care of. Eager for more options? Browse the amazing offers on our standard 4-star stays in and around Winchester too.