Hotels and Motels near Chester, MD
Chester is on Kent Island in eastern Maryland. It is 44 miles southeast of
Baltimore .
Note: Add 20 miles for hotels in St Michaels.
Zoom in (+) to see interstate exits, restaurants, and other attractions near hotels.
Inn at Chesapeake Bay Stevensville
180 Pier One Road, Stevensville, MD 21666
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1.9 miles
1.9 miles from Chester
From $239
Check In 16 00
Check Out 11 00
Rated Very High
Upscale, smoke-free, full-service hotel
Near US 50 and Terrapin Beach Park
3 floors, 44 rooms and suites - elevator
No swimming pool
Exercise room
2 restaurants - lounge
Free WiFi
Free parking Not pet friendly
TripAdvisor Traveler Rating:
Based on 179 reviews
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Hyatt Place Hotel Kent Narrows & Marina Grasonville
3028 Kent Narrow Way South, Grasonville, MD 21638
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2.5 miles
2.5 miles from Chester
From $155
Check In 16 00
Check Out 11 00
Upscale, smoke-free, waterfront hotel & marina
Located in historic Fisherman's Village
4 floors, 120 rooms
Heated indoor swimming pool - 24-hour exercise room
Restaurant - lounge
Free hot breakfast buffet
Free WiFi
Free parking Pet friendly hotel
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- allows one dog up to 50 pounds or 2 dogs with a combined weight of 75 pounds - $100 pet fee if staying fewer than 7 nights - and additional $100 pet fee if staying 7-30 nights. - Mar 2023 < Less
Best Western Kent Narrows Inn Grasonville
3101 Main Street, Grasonville, MD 21638
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2.6 miles
2.6 miles from Chester
From $229
Check In 1600
Check Out 1100
Rated Average
Midscale, smoke-free hotel
Near Wells Cove and US 50 at US 301, Exit 41
Heated indoor swimming pool - exercise room
Free hot breakfast buffet
Free WiFi
Free parking - limited truck parking Pet friendly hotel
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- pets allowed only in 1st and 2nd floor rooms, 2 pets per room - $30 per night pet fee. - Aug 2021 < Less
TripAdvisor Traveler Rating:
Based on 818 reviews
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"My hotel stay was fine.2023-04-28 "
"I wasn't informed that the motel was undergoing renovations. 2016-03-01 "
"Good location, but the motel needed renovation. The room door was broken at the base, and the carpet was dirty. I had to clean the toilet myself because the bathroom was dirty. Go somewhere else.2015-05-07 "
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Hilton Garden Inn Kent Island Grasonville
3206 Main Street, Grasonville, MD 21638
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2.7 miles
2.7 miles from Chester
From $138
Check In 15 00
Check Out 12 00
Rated High
Upscale, smoke-free hotel
Near Wells Cove and US 50/US 301, Exit 42
5 floors, 90 rooms
Heated indoor swimming pool - exercise room
Restaurant - lounge - room service
Restaurant open for breakfast and dinner only
Microwave and refrigerator in every room
Free WiFi
Free parking Not pet friendly
TripAdvisor Traveler Rating:
Based on 1070 reviews
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"The hotel room was large and bright, and overlooked the arena. All the employees we encountered were friendly and helpful.2023-06-12 "
"Located in the middle of nowhere. The fridge in the room didn't work. No instructions for the whirlpool, and no grab bars in the shower. The balcony was sub-par. The room had a view of the parking lot and beer kegs from the bar below. Breakfast wasn't good. Don't stay at this hotel.2021-06-25 "
"Everything about this hotel was fantastic, and there were great restaurants in the area. Ask for a room facing the water.2018-06-03 "
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Holiday Inn Express Grasonville
1020 Kent Narrows Road, Grasonville, MD 21638
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2.8 miles
2.8 miles from Chester
From $102
Check In 15 00
Check Out 11 00
Rated High
Upper-midscale, smoke-free, waterfront hotel
Near Wells Cove and US 50/US 301, Exit 42
3 floors, 75 rooms - elevator
Outdoor swimming pool open in summer
Free hot breakfast buffet
Free WiFi
Free parking - truck parking Not pet friendly
TripAdvisor Traveler Rating:
Based on 266 reviews
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"The hotel room was large, with a great view of the water. The bathroom was spacious and clean. There was an outdoor pool. Ask for a room on the 3rd floor for a good view.2021-06-17 "
"The hotel room was cleaned each day and fresh linens were provided. You'll have an enjoyable stay.2018-11-05 "
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Annapolis Waterfront Hotel
80 Compromise Street, Annapolis, MD 21401
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11 miles
11 miles from Chester
From $120
Check In 1600
Check Out 1100
Rated Average
Upper-upscale, smoke-free, full-service, waterfront hotel
Located in downtown Annapolis
An Autograph Collection hotel
6 floors, 150 rooms and suites
No swimming pool
Exercise room
Restaurant - lounge - room service
Free WiFi
Valet parking only - $30 per night Pet friendly hotel
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- allows up to 2 pets per room - $100 per stay pet fee. - Aug 2021 < Less
TripAdvisor Traveler Rating:
Based on 636 reviews
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"The hotel room was clean but basic; there was nothing special about it. We'd asked for a room on a lower floor with a waterfront view, but were given a room on the 2nd highest floor facing the street.2023-10-09 "
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Historic Inns Annapolis
58 State Circle, Annapolis, MD 21401
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11 miles
11 miles from Chester
From $256
Check In 16 00
Check Out 11 00
Rated High
Midscale, smoke-free, downtown Annapolis hotel
Near US Naval Academy
Member of Historic Hotels of America
3 buildings - 4 floors; 124 rooms, 9 suites
Free shuttle to local attractions
No swimming pool
Exercise room
Lounge
Free WiFi
Valet parking only - $30 per night Not pet friendly
TripAdvisor Traveler Rating:
Based on 1524 reviews
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"The hotel was conveniently located, and the check-in clerk was helpful. The valet parking was worth the price due to parking problems during Navy home games.2017-10-25 "
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Graduate Hotel Annapolis
126 West Street, Annapolis, MD 21401
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11 miles
11 miles from Chester
From $159
Check In 16 00
Check Out 11 00
Rated Very High
Upper-upscale, smoke-free, downtown hotel
Near historic district
No swimming pool
24-hour exercise room
Restaurant - lounge
Restaurant open for lunch and dinner only
Free WiFi
Parking costs $26 per night Pet friendly hotel
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- allows pets in 2nd floor rooms only, 2 pets per room - $25 per night pet fee. - Nov 2020 < Less
TripAdvisor Traveler Rating:
Based on 729 reviews
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"Convenient to downtown and waterfront activities. The room was super comfortable and quiet. Easy check-in and checkout. You'll love it.2018-10-20 "
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Hilton Garden Inn Downtown Annapolis
174 West Street, Annapolis, MD 21401
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11 miles
11 miles from Chester
From $336
Check In 15 00
Check Out 12 00
Rated High
Upscale, smoke-free, downtown hotel 5 floors, 120 rooms and suites No swimming pool Exercise room Restaurant - lounge - room service Restaurant open for breakfast and dinner only Microwave and refrigerator in every room Free WiFi Valet parking only - $26 per night Not pet friendly
TripAdvisor Traveler Rating:
Based on 247 reviews
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Westin Hotel Annapolis
100 Westgate Circle, Annapolis, MD 21401
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12 miles
12 miles from Chester
From $219
Check In 1600
Check Out 1100
Rated High
Upscale, smoke-free, full-service, downtown Annapolis hotel
6 floors, 225 rooms and suites
Heated indoor swimming pool - exercise room
Restaurant - lounge - room service
Internet access costs $10 per night
Parking costs $20 per night Pet friendly hotel
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- allows dogs only up to 45 pounds - $50 per stay pet fee. - Jul 2016 < Less
TripAdvisor Traveler Rating:
Based on 1300 reviews
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Inn at Perry Cabin St Michaels
308 Watkins Lane, St Michaels, MD 21663
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13 miles
13 miles from Chester
From $241
Check In 16 00
Check Out 11 00
Rated Very High
Luxury, smoke-free, full-service, waterfront hotel
Located one-half mile north of downtown St Michaels
3 floors, 78 rooms - elevator Outdoor swimming pool open in summer Exercise room
Restaurant - lounge
Full-service spa Pet friendly hotel
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- $150 per stay pet fee. - Jan 2019 < Less
Note: This hotel charges a resort fee of 10% - includes parking and WiFi.
TripAdvisor Traveler Rating:
Based on 1355 reviews
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Crowne Plaza Hotel Annapolis
173 Jennifer Road, Annapolis, MD 21401
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13 miles
13 miles from Chester
From $80
Check In 16 00
Check Out 11 00
Rated Average
Upscale, smoke-free, full-service hotel near Annapolis Mall
Heated indoor swimming pool - fitness center
Restaurant - lounge - room service
Restaurant open for breakfast and dinner only
Free WiFi
Free parking Pet friendly hotel
More >
- $50 per stay fee for each pet. - Oct 2015 < Less
TripAdvisor Traveler Rating:
Based on 743 reviews
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"The hotel room was clean and quiet, and the lobby had comfortable seating. The staff was courteous and helpful.2022-03-08 "
"Great hotel. I had a comfortable stay.2021-05-10 "
"We had a wonderful stay at this hotel.2019-04-24 "
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Holiday Inn Express & Suites Annapolis
2451 Riva Road, Annapolis, MD 21401
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13 miles
13 miles from Chester
From $95
Check In 15 00
Check Out 11 00
Rated Average
Upper-midscale, smoke-free hotel
Near Annapolis Mall and US Navel Academy
2 floors, 79 rooms and suites - elevator
No swimming pool
Exercise room
Microwave and refrigerator in every room
Free hot breakfast buffet
Free WiFi
Free parking Not pet friendly
TripAdvisor Traveler Rating:
Based on 419 reviews
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"Not a bad hotel all in all. No washcloths in the room until I requested some. Too much noise from one room one night.2022-10-10 "
"The hotel was clean and comfortable; it was much better than comparably priced hotels in the area that I've stayed in.2019-07-03 "
"My only complaint was that the curtains were too sheer. Great breakfast with a nice selection. I definitely recommend this hotel.2016-02-17 "
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DoubleTree by Hilton Hotel Annapolis
210 Holiday Court, Annapolis, MD 21401
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14 miles
14 miles from Chester
From $148
Check In 16 00
Check Out 12 00
Rated High
Upscale, smoke-free, full-service hotel near Annapolis Mall
6 floors, 219 rooms and suites
Free shuttle to attractions within 5-mile radius Outdoor swimming pool open in summer Exercise room
Restaurant - lounge - room service
Free WiFi
Free parking Pet friendly hotel
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- $50 per stay pet fee. - May 2015 < Less
TripAdvisor Traveler Rating:
Based on 1466 reviews
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"The hotel room was clean and spacious, and the bed was adequately comfortable. The shuttle driver was awesome and made our trip better.2022-10-11 "
"Great hotel in a nice location.2018-08-28 "
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Best Western Annapolis Hotel
2520 Riva Road, Building B, Annapolis, MD 21401
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14 miles
14 miles from Chester
From $87
Check In 1500
Check Out 1100
Rated Average
Midscale motel near Annapolis Mall
2 floors, 151 rooms - no elevator
Some smoking rooms Outdoor swimming pool open in summer Exercise room
Free continental breakfast
Free WiFi
Free parking - truck parking Pet friendly motel
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- pets allowed only in some 1st floor rooms - $20 per night fee for each pet. - Aug 2021 < Less
TripAdvisor Traveler Rating:
Based on 639 reviews
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"The floors in our hotel room were filthy, and the shower mat was dirty. We could hear the people in the room above ours walking around.2022-03-29 "
"Nice place to stay.2020-07-14 "
"The room had ants, the floors were dirty, and the door handle was broken so I couldn't get out of the room. Don't stay here.2020-07-06 "
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Red Roof Inn West Annapolis
2520 Riva Road, Building C, Annapolis, MD 21401
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14 miles
14 miles from Chester
From $76
Check In 15 00
Check Out 11 00
Rated High
Cheap, smoke-free hotel near Ann Arundel Medical Center
Also near US 50 at MD 665
2 floors, 47 rooms - no elevator
No swimming pool
Free WiFi
Free parking - truck parking Pet friendly hotel
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- allows pets up to 80 pounds, 2 pets per room - no pet fee. - Jun 2018 < Less
TripAdvisor Traveler Rating:
Based on 17 reviews
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"The hotel room was clean, economical, and pet friendly. The staff was courteous. Limited amenities, so maybe not the best choice for an extended stay.2018-11-30 "
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Hampton Inn & Suites Annapolis
124 Womack Drive, Annapolis, MD 21401
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14 miles
14 miles from Chester
From $95
Check In 16 00
Check Out 11 00
Rated High
Upper-midscale, smoke-free hotel near Annapolis Mall
Heated outdoor swimming pool open in summer
Exercise room
Free hot breakfast buffet
Free WiFi
Free parking Pet friendly hotel
More >
- $75 per stay pet fee. - Oct 2018 < Less
TripAdvisor Traveler Rating:
Based on 1041 reviews
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"The service at this hotel was excellent.2017-09-12 "
"Not many restaurants near this hotel. Breakfast was outstanding, though; great food and plenty of it.2016-06-21 "
"Close to restaurants and shops, and the rates were fair. All the hotel employees were friendly and helpful and accommodating toward our dog. Lots of choices at the complimentary breakfast, and I liked the extended hours. Plenty of parking. I'd stay here again.2015-11-30 "
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SpringHill Suites by Marriott Annapolis
189 Admiral Cochrane Drive, Annapolis, MD 21401
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14 miles
14 miles from Chester
From $118
Check In 1500
Check Out 1200
Rated Very High
Upscale, smoke-free, all-suite hotel Located near Annapolis Mall 4 floors, 120 studio suites Heated indoor swimming pool - exercise room Microwave and refrigerator in every suite Free hot breakfast buffet Free WiFi Free parking Not pet friendly
TripAdvisor Traveler Rating:
Based on 729 reviews
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"The hotel was clean and quiet, and the employees were professional.2021-05-19 "
"Located in the middle of everything we wanted to see. The hotel was clean, but ask for a room away from the stairwell. Wish the pool opened earlier. Breakfast was enjoyable.2016-05-04 "
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Hotels near Me
Hotels near Kent Island Resort 1.6 miles SW
Hotels near Red Eye's Dock Bar 2.3 miles east
Hotels near Chesapeake Bay Beach Club 2.4 miles west
Hotels near Jetty Dock Bar 2.6 miles east
Hotels near Bay Bridge MD 4.3 miles west
Hotels near Kentmorr Restaurant 6 miles SW
Hotels near Sandy Point State Park 7 miles NW
Hotels near Annapolis Maritime Museum 10 miles west
Hotels near Chesapeake Bay MD 10 miles SW
Hotels near USNA Naval Academy 10 miles west
Hotels near Annapolis Harbor 11 miles west
Hotels near Annapolis City Dock 11 miles west
Hotels near Annapolis Boat Show 11 miles west
Hotels near Annapolis Waterfront 11 miles west
Hotels near Maryland State House 11 miles west
Stevensville MD Hotels 1.4 miles west
Kent Narrows MD Hotels 2.8 miles east
Kent Island MD Hotels 3.4 miles SW
Grasonville MD Hotels 4.2 miles east
Queenstown MD Hotels 7 miles east
Chesapeake Bay MD Hotels 10 miles SW
Annapolis MD Hotels 11 miles west
Arnold MD Hotels 12 miles west
Centreville MD Hotels 13 miles east
St Michaels MD Hotels 14 miles south
Edgewater MD Hotels 15 miles west
Severna Park MD Hotels 15 miles NW
Crownsville MD Hotels 17 miles west
Pasadena MD Hotels 18 miles NW
Georgetown MD Hotels 18 miles north
On place pages like this, we order hotels from lowest cost to highest except we list low-rated hotels at the bottom of the page.
Most of our competitors order these same hotels in other ways that make them more money.
To us, motels are smaller lodgings that have rooms you can enter directly from the parking area.
At hotels , on the other hand, you can enter your room only through a hall inside the building.
Beware of non-refundable reservations that could cost you a lot of money if you change or cancel them. + Non-refundable reservations are a gamble that will usually save you less than $10. If you make a $90 non-refundable reservation instead of a $100 refundable booking, you are betting $90 to win $10. Would you do that in Las Vegas? -
Don't assume you can cancel a non-refundable reservation without penalty if you notify the hotel weeks or even months in advance. + Often you cannot because some hotels' profit strategy is to get paid more than once for the same room for the same night. -
Always read cancellation policies carefully before you make a reservation. + When is the latest date and time you can cancel without penalty? - More >
When you make a reservation, you will receive a confirmation email. Take a copy with you to the hotel.
The earlier in the afternoon you check into a hotel, the more likely you will get a room or suite that matches your preferences.
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