Find 4 Star Hotels in Winchester, IL

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 availability on Winchester 4 Star Hotels

Tonight
27 Nov - 28 Nov
Tomorrow
28 Nov - 29 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Compare Winchester 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Front of property
Villa DeWolf

Villa DeWolf

4.0 star property
Jacksonville
10.0 out of 10, Exceptional, (11)
"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!"
Canada
Catherine
Villa DeWolf
Property grounds
Blessings on State Bed & Breakfast

Blessings on State Bed & Breakfast

4.0 star property
Jacksonville
9.4 out of 10, Exceptional, (55)
"Excellent property with welcoming staff and cozy, well-appointed rooms. "
United States
James
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

Villa DeWolf

Villa DeWolf

10/10 Excellent
"The owner communicated early and often to make sure we were good upon arrival. The house is beautiful and well appointed. The rooms are upstairs but the butler Kimo will bring up your luggage. The room was spacious and bathroom had everything needed - even 2 robes!! Breakfast was amazing - home cooked and very filling. I'm a vegetarian and he accommodated me easily. Would stay there again. "
Deborah 3-night trip
Posted 5 months ago
Villa DeWolf

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 vacation 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 traveler experience and upscale décor, 4-star hotels are a terrific option for your Winchester escape. These kinds of accommodations 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?
Use our "All inclusive" filter to find your dream hotel in Winchester where everything is taken care of, from your room to your meals, entertainment and activities. We can also help you find standard 4-star stays in and around this amazing destination.

Explore a world of travel with Expedia