Luxury Hotels & Resorts in Chester from AU$158

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Chester Luxury Hotels

Our top choices for Chester luxury hotels

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,003 reviews)
The price is AU$181
includes taxes & fees
5 July - 6 July
DoubleTree by Hilton Hotel Annapolis

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (390 reviews)
  • cleanliness
    Waterfront luxury awaits with golf, spa, and marina at this St. Michaels coastal retreat.
The price is AU$1,120
includes taxes & fees
9 July - 10 July
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, (461 reviews)
The price is AU$393
includes taxes & fees
22 June - 23 June
The Inn at Chesapeake Bay Beach Club

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (42 reviews)
The price is AU$690
includes taxes & fees
21 June - 22 June
The Oaks Waterfront

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Historic district hotel blends Beaux Arts elegance with spa luxury, featuring lavish treatments near Annapolis attractions.
The price is AU$275
includes taxes & fees
5 July - 6 July
The Westin Annapolis

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (16 reviews)
  • cleanliness
    Indulge in beachside luxury at this 5-star estate featuring a seasonal outdoor pool, private balconies, and Italian Frette sheets.
The price is AU$531
includes taxes & fees
13 July - 14 July
The Inn at Tacaro Estate

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (938 reviews)
The price is AU$405
includes taxes & fees
21 June - 22 June
Annapolis Waterfront Hotel, Autograph Collection

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.2 out of 10, Wonderful, (1,012 reviews)
  • cleanliness
    Upscale Annapolis retreat offers nautical elegance with Egyptian cotton linens and pillowtop beds.
The price is AU$265
includes taxes & fees
12 July - 13 July
Graduate by Hilton 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.

Explore a world of travel with Expedia