Photo by Patricia Knorr

Luxury Hotels & Resorts in Chester

    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 Chester Luxury Hotels

Best Chester Luxury Hotels

Top Chester Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Great place for a quick get away!"
Phyllis 1-night trip
Posted 2 days ago
Historic Inns of Annapolis

Frequently asked questions

Are you looking for a luxury hotel for your stay in Chester?
Use Expedia and let us help you arrange a flight to Easton, MD (ESN-Easton - Newnam) airport or Baltimore Washington International Airport (BWI) airport, and then select from different places to stay that will deliver the luxury you want. Amenities are an important consideration when you plan a holiday, so we make it easy to get what you need to make your stay special. If you want a posh hotel that has fine dining, a spa or several swimming pools, Expedia can help you find the best luxury hotel experience that Chester offers.
When can I expect good weather in Chester?
Planning for the weather is an important factor for making your trip to Chester a success, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chester is 1414 mm.
What's there to see and do in Chester?
When you're in Chester, enjoy exploring the sights and attractions here including Matapeake State Park, Chesapeake Bay Environmental Center and Love Point State Park. If you have extra time while you're in the area, you might want to see Eastern Neck National Wildlife Refuge and Sandy Point Beach.