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Find luxury hotels in Chester, MD

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Top Chester Luxury Hotels

Find out more about Chester

Chesterand its attractions for luxury travelers

Chester, Maryland, offers a unique blend of luxury and natural beauty that will captivate travelers. Begin your journey at the Chesapeake Bay Environmental Center, where you can stroll along scenic trails, enjoy birdwatching, and take in the stunning views of the bay. For a taste of local culture, visit the quaint town of Chestertown, just a short drive away, known for its historic charm and artisan shops. If you’re seeking relaxation, the nearby Kent Narrows offers upscale waterfront dining with fresh seafood and picturesque sunset views. Adventurous travelers can indulge in sailing or charter fishing excursions that provide an exhilarating way to explore the bay. After a day of exploration, unwind in one of the luxury hotels located along the waterfront, where you can enjoy spacious rooms, personalized service, and exquisite amenities. The area is perfect for families and couples alike, ensuring that every stay is a memorable experience.

Top Chester Hotel Reviews

St Michaels Inn

St Michaels Inn

10/10 Excellent
"yes"
charles 2-night trip
Posted 4 days ago
St Michaels Inn

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 Intl. 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 trip, so we make it easy to get what you want to make your stay special. If you want a posh hotel with 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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chester is 56 inches.
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.

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