Winchester 4 Stars Hotels

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Check availability on Winchester 4 Star Hotels

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

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
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Learn more about Winchester

Check out Morgan County Fairgrounds and Lake Jacksonville—just a couple of the sights around Winchester.

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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 1 month ago
Villa DeWolf
Blessings on State Bed & Breakfast

Blessings on State Bed & Breakfast

10/10 Excellent
"Excellent property with welcoming staff and cozy, well-appointed rooms. "
James 1-night trip
Posted 11 months ago
Blessings on State Bed & Breakfast

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.

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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?
Enjoy a stress-free vacation 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, accommodations 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.