A boat docked at a pier during twilight with a city skyline in the background.

Luxury Hotels & Resorts in Chester from AU$136

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Check availability on Chester Luxury Hotels

Tonight
17 Sept - 18 Sept
Tomorrow
18 Sept - 19 Sept
This weekend
18 Sept - 20 Sept
Next weekend
25 Sept - 27 Sept

Our top choices for Chester luxury hotels

1. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
AU$349
includes taxes & fees
4 Oct - 5 Oct
The Inn at Chesapeake Bay Beach Club

2. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Historic district hotel blends Beaux Arts elegance with spa luxury, featuring lavish treatments near Annapolis attractions.
AU$288
includes taxes & fees
27 Sept - 28 Sept
The Westin Annapolis

3. DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
Annapolis
AU$136
includes taxes & fees
20 Sept - 21 Sept
DoubleTree by Hilton Hotel Annapolis

4. Graduate by Hilton Annapolis

Graduate by Hilton Annapolis
Annapolis
  • Upscale Annapolis retreat offers nautical elegance with Egyptian cotton linens and pillowtop beds.
AU$238
includes taxes & fees
27 Sept - 28 Sept
Graduate by Hilton Annapolis

5. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
AU$383
includes taxes & fees
30 Sept - 1 Oct
Annapolis Waterfront Hotel, Autograph Collection

6. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
  • Waterfront luxury awaits with golf, spa, and marina at this St. Michaels coastal retreat.
AU$936
includes taxes & fees
13 Oct - 14 Oct
Inn at Perry Cabin

7. The Oaks Waterfront

The Oaks Waterfront
Easton
AU$683
includes taxes & fees
20 Sept - 21 Sept
The Oaks Waterfront

8. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
  • Indulge in beachside luxury at this 5-star estate featuring a seasonal outdoor pool, private balconies, and Italian Frette sheets.
AU$625
includes taxes & fees
18 Oct - 19 Oct
The Inn at Tacaro Estate
View all properties

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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"Great hotel, close to downtown, and in a nice area! Great staff!!!"
Daniel 2-night trip
Posted 3 hours ago
DoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Very impressed with the staff and all the help they provided for us.....! Cleanliness tops. My only complaint is with the cable TV quality. Very poor picture quality and cumbersome remote. This certainly requires a big upgrade. Also it wasn`t till the second day that I found electric outlets for charging phones , etc , on the face of the bedside stands and table If you outline the outlets with a narrow line of white tape, they would be easily noticed , The outlets were dark and against the dark wood of the furniture in low lit rooms was almost impossible to see. Small peanuts, but a easy upgrade. We enjoyed our stay !!! Thanks"
Pamela 2-night trip
Posted 22 hours ago
Historic Inns of Annapolis
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"This is a fabulous resort! Very clean, great location and the staff is great!"
Bobbi 1-night trip
Posted 3 days ago
The Westin Annapolis
St Michaels Inn

St Michaels Inn

8/10 Good
"The one issue was there were flies in our room and a squished bug came on our wall. There also were cobwebs in the corner. Not enough pillows and old."
Rachel 1-night trip
Posted 3 days ago
St Michaels Inn
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Room was amazing. Staff is super friendly and helpful. Plenty of parking. Would definitely stay again."
Michael 2-night trip
Posted 3 days ago
Country Inn & Suites by Radisson, Annapolis, MD
Best Western Annapolis

Best Western Annapolis

10/10 Excellent
"Breakfast was really good but they never did get our door key to work properly. Room was very clean and bed was comfortable. Staff was very friendly and helpful but the outside of the rooms, such as doors needs serious upgrades."
Jane 1-night trip
Posted 4 days ago
Best Western Annapolis
Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"It’s so lovely and elegant I almost don’t want to tell people it’s there. Stunning, perfect in every way."
Susan 1-night trip
Posted 9 days ago
Inn at Perry Cabin

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 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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