Luxury Hotels & Resorts in Chester from AU$125

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Our top choices for Chester luxury hotels

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41 reviews)
" Beautiful property, wonderful staff, excellent food service."
United States
Seth
The price is AU$645
includes taxes & fees
15 Feb - 16 Feb
The Oaks Waterfront

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (374 reviews)
"Beautiful place to stay."
United States
Ellen
The price is AU$744
includes taxes & fees
27 Feb - 28 Feb
Inn at Perry Cabin

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (434 reviews)
"Amazing rooms and service!"
United States
Alicia
The price is AU$285
includes taxes & fees
3 Feb - 4 Feb
The Inn at Chesapeake Bay Beach Club

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (901 reviews)
"Great location, nice and clean "
United States
Micah
The price is AU$360
includes taxes & fees
8 Feb - 9 Feb
Annapolis Waterfront Hotel, Autograph Collection

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1,001 reviews)
"Room was clean, great location"
United States
Brian
The price is AU$257
includes taxes & fees
22 Feb - 23 Feb
Graduate by Hilton Annapolis

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,000 reviews)
"Great hotel love that they are pet friendly. Easy check in and valet parking staff great"
United States
Robert
The price is AU$277
includes taxes & fees
15 Feb - 16 Feb
The Westin Annapolis

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (12 reviews)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
The Inn at Tacaro Estate

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,000 reviews)
"Great stay "
United States
Jose Miguel
The price is AU$125
includes taxes & fees
8 Feb - 9 Feb
DoubleTree by Hilton Hotel Annapolis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find out more about Chester

Chesterand its attractions for luxury travelers

Chester, Maryland, offers an enticing blend of luxurious experiences and picturesque surroundings for discerning travellers. Begin your exploration at the serene Kent Narrows, where you can indulge in a waterfront dining experience at one of the upscale restaurants, enjoying fresh seafood while watching the boats glide by. For those who appreciate the arts, the nearby Chesapeake Bay Maritime Museum provides an enriching glimpse into local history and culture, housed in beautifully restored buildings with stunning views of the bay. Golf enthusiasts will relish a round at the exclusive Queenstown Harbor Golf Club, featuring two championship courses that promise both challenge and breathtaking vistas. Nature lovers can take a leisurely stroll along the picturesque trails of the Blackwater National Wildlife Refuge, where you can spot migratory birds and experience the tranquillity of the Chesapeake landscapes. After your adventures, retreat to one of the luxurious hotels in the Kent Narrows area, known for its upscale amenities and personalised service, ensuring that your stay is as enjoyable as your explorations. Each hotel offers stunning water views and excellent access to local attractions, making your visit to Chester both relaxing and unforgettable.

Top Chester Hotel Reviews

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 Northern Chesapeake Bay, Matapeake State Park and Chesapeake Bay Environmental Center. If you have extra time while you're in the area, you might want to see Love Point State Park and Sandy Point Beach.

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