Hotels below are sorted by distance from Chester.
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.
Rates shown below are averages. Click See Rates to view rates for your dates.
1.9 miles
Inn at Chesapeake Bay Stevensville
180 Pier One Road, Stevensville, MD 21666
1.9 miles from Chester
Enter Dates
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
No swimming pool
Exercise room
Free WiFi
Free parking
Not pet friendly
- no pets allowed. - Apr 2016
TripAdvisor Traveler Rating: Based on 145 reviews
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2.6 miles
Best Western Kent Narrows Inn Grasonville
3101 Main Street, Grasonville, MD 21638
2.6 miles from Chester
Enter Dates
From $229
Check In 1600 Check Out 1100
Rated High
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
More >
- pets allowed only in 1st and 2nd floor rooms, 2 pets per room - $30 per night pet fee. - Aug 2021
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"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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TripAdvisor Traveler Rating: Based on 738 reviews
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2.7 miles
Hilton Garden Inn Kent Island Grasonville
3206 Main Street, Grasonville, MD 21638
2.7 miles from Chester
Enter Dates
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
Heated indoor swimming pool - exercise room
Free WiFi
Free parking
Not pet friendly
- no pets allowed. - Sep 2015
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"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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TripAdvisor Traveler Rating: Based on 1039 reviews
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2.8 miles
Holiday Inn Express Grasonville
1020 Kent Narrows Road, Grasonville, MD 21638
2.8 miles from Chester
Enter Dates
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
Outdoor swimming pool open in summer
Free hot breakfast buffet
Free WiFi
Free parking - truck parking
Not pet friendly
- no pets allowed. - May 2021
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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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TripAdvisor Traveler Rating: Based on 256 reviews
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10 miles
Rodeway Inn Annapolis
74 Old Mill Bottom Road North, US 50, Exit 28, Annapolis, MD 21409
10 miles from Chester
Enter Dates
From $59
Check In 15 00 Check Out 11 00
Rated Average
Cheap motel 4 miles from Sandy Point State Park
Some smoking rooms
No swimming pool
Free WiFi
Free parking
Not pet friendly
- no pets allowed. - Jul 2015
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"The motel was clean, well-maintained, safe, and reasonably priced. The staff was friendly and accommodating.2018-07-03 "
"OK motel for the price. The bathroom door wouldn't close.2017-10-05 "
"Inexpensive motel, but the room was sorely in need of a makeover. There were signs of water damage in the bathroom, and I had trouble accessing the Internet. No one answered the phone when I called the front desk. You get what you pay for, but we had the essentials.2016-07-06 "
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TripAdvisor Traveler Rating: Based on 139 reviews
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11 miles
Annapolis Waterfront Hotel
80 Compromise Street, Annapolis, MD 21401
11 miles from Chester
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From $120
Check In 1600 Check Out 1100
Rated High
Upper-upscale, smoke-free, full-service, waterfront hotel
Located in downtown Annapolis
An Autograph Collection hotel
No swimming pool
Exercise room
Free WiFi
Valet parking only - $30 per night
Pet friendly hotel
More >
- allows up to 2 pets per room - $100 per stay pet fee. - Aug 2021
TripAdvisor Traveler Rating: Based on 611 reviews
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11 miles
Quality Inn US Naval Academy Annapolis
76 Old Mill Bottom Road North, Annapolis, MD 21401
11 miles from Chester
Enter Dates
From $85
Check In 15 00 Check Out 11 00
Rated High
Midscale, smoke-free hotel
5.5 miles from near Sandy Point State Park
No swimming pool
Exercise room
Free hot breakfast buffet
Free WiFi
Free parking
Not pet friendly
- no pets allowed. - Aug 2019
Most Recent HotelGuides Reviews
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"The hotel was clean and nicely appointed. Stay here.2019-11-06 "
"Convenient location. The hotel was comfortable, and the staff was nice.2017-04-16 "
"Close to downtown. The hotel room was nice, clean, and quiet, and it was perfectly cleaned each day. The staff was friendly. Good place to stay.2016-07-09 "
"The hotel was clean and comfortable, and the staff was kind and helpful.2016-04-23 "
"Our room was clean and comfortable, and the hotel staff was friendly.2015-11-16 "
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TripAdvisor Traveler Rating: Based on 134 reviews
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11 miles
Historic Inns Annapolis
58 State Circle, Annapolis, MD 21401
11 miles from Chester
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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
Free shuttle to local attractions
No swimming pool
Exercise room
Free WiFi
Valet parking only - $30 per night
Not pet friendly
- no pets allowed. - Feb 2020
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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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TripAdvisor Traveler Rating: Based on 1434 reviews
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11 miles
Graduate Hotel Annapolis
126 West Street, Annapolis, MD 21401
11 miles from Chester
Enter Dates
From $159
Check In 16 00 Check Out 11 00
Rated High
Upper-upscale, smoke-free, downtown hotel
Near historic district
No swimming pool
24-hour exercise room
Free WiFi
Parking costs $26 per night
Pet friendly hotel
More >
- allows pets in 2nd floor rooms only, 2 pets per room - $25 per night pet fee. - Nov 2020
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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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TripAdvisor Traveler Rating: Based on 239 reviews
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11 miles
Hilton Garden Inn Downtown Annapolis
174 West Street, Annapolis, MD 21401
11 miles from Chester
Enter Dates
From $336
Check In 15 00 Check Out 12 00
Rated High
Upscale, smoke-free, downtown hotel No swimming pool Exercise room Free WiFi Valet parking only - $26 per night
Not pet friendly
- no pets allowed. - Jul 2018
TripAdvisor Traveler Rating: Based on 221 reviews
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13 miles
Inn at Perry Cabin St Michaels
308 Watkins Lane, St Michaels, MD 21663
13 miles from Chester
Enter Dates
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
Outdoor swimming pool open in summer - exercise room
Full-service spa
Pet friendly hotel
More >
- $150 per stay pet fee. - Jan 2019
Note: This hotel charges a resort fee of 10% - includes parking and WiFi.
TripAdvisor Traveler Rating: Based on 1330 reviews
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13 miles
Westin Hotel Annapolis
100 Westgate Circle, Annapolis, MD 21401
13 miles from Chester
Enter Dates
From $219
Check In 1600 Check Out 1100
Rated High
Upscale, smoke-free, full-service, downtown Annapolis hotel
Heated indoor swimming pool - exercise room
Internet access costs $10 per night
Parking costs $20 per night
Pet friendly hotel
More >
- allows dogs only up to 45 pounds - $50 per stay pet fee. - Jul 2016
TripAdvisor Traveler Rating: Based on 1119 reviews
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13 miles
Crowne Plaza Hotel Annapolis
173 Jennifer Road, Annapolis, MD 21401
13 miles from Chester
Enter Dates
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
Free WiFi
Free parking
Pet friendly hotel
More >
- $50 per stay fee for each pet. - Oct 2015
Most Recent HotelGuides Reviews
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"Great hotel. I had a comfortable stay.2021-05-10 "
"We had a wonderful stay at this hotel.2019-04-24 "
"I stayed at this hotel for 2 nights. The room was comfortable. Nice dining in the Annapolis Bar and Grill. Take advantage of the pool.2015-09-08 "
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TripAdvisor Traveler Rating: Based on 678 reviews
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14 miles
Holiday Inn Express & Suites Annapolis
2451 Riva Road, Annapolis, MD 21401
14 miles from Chester
Enter Dates
From $95
Check In 15 00 Check Out 11 00
Rated High
Upper-midscale, smoke-free hotel
Near Annapolis Mall and US Navel Academy
No swimming pool
Exercise room
Free hot breakfast buffet
Free WiFi
Free parking
Not pet friendly
- no pets allowed. - Jul 2021
Most Recent HotelGuides Reviews
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"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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TripAdvisor Traveler Rating: Based on 410 reviews
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14 miles
Extended Stay America Suites Annapolis
1 Womack Drive, Annapolis, MD 21401
14 miles from Chester
Enter Dates
From $68
Check In 15 00 Check Out 11 00
Rated Average
Budget, all-suite, extended-stay hotel near Annapolis Mall
Some smoking rooms
No swimming pool
Kitchen in every suite
Free continental breakfast
Free WiFi
Free parking
Pet friendly hotel
More >
- $25 per night fee for each pet - $150 maximum per stay fee for each pet. - Jul 2015
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"The hotel clerk put me at ease, and she was efficient and quick. We were pleased that our smoking room was clean, and the bathroom was spotless. The kitchen was just what we needed.2021-08-26 "
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TripAdvisor Traveler Rating: Based on 140 reviews
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14 miles
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court, Annapolis, MD 21401
14 miles from Chester
Enter Dates
From $148
Check In 16 00 Check Out 12 00
Rated High
Upscale, smoke-free, full-service hotel near Annapolis Mall Free shuttle to attractions within 5-mile radius Outdoor swimming pool open in summer - exercise room Free WiFi Free parking
Pet friendly hotel
More >
- $50 per stay pet fee. - May 2015
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"Great hotel in a nice location.2018-08-28 "
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TripAdvisor Traveler Rating: Based on 1432 reviews
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14 miles
Best Western Annapolis Hotel
2520 Riva Road, Building B, Annapolis, MD 21401
14 miles from Chester
Enter Dates
From $87
Check In 1500 Check Out 1100
Rated Average
Midscale motel near Annapolis Mall
Some smoking rooms
Outdoor swimming pool open in summer - exercise room
Free continental breakfast
Free WiFi
Free parking - truck parking
Pet friendly motel
More >
- pets allowed only in some 1st floor rooms - $20 per night fee for each pet. - Aug 2021
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"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 "
"Located off the main road, so the hotel was quiet but convenient to restaurants and stores. The room was clean and comfortable, and the in-room coffee was delicious. No heat the 1st night, so I was moved to another room. The employees were nice and helpful. We had a comfortable stay.2017-11-17 "
"Not a 5-star hotel by any means, but the room was clean and the rates were good. Great continental breakfast. I recommend staying here.2016-02-17 "
"Easy access to everything. Excellent rates for the area. The hotel room was clean and quiet, and the staff was friendly and courteous. Good breakfast.2015-08-29 "
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TripAdvisor Traveler Rating: Based on 620 reviews
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14 miles
Red Roof Inn West Annapolis
2520 Riva Road, Building C, Annapolis, MD 21401
14 miles from Chester
Enter Dates
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
No swimming pool
Free WiFi
Free parking - truck parking
Pet friendly hotel
More >
- allows pets up to 80 pounds, 2 pets per room - no pet fee. - Jun 2018
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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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TripAdvisor Traveler Rating: Based on 17 reviews
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14 miles
Hampton Inn & Suites Annapolis
124 Womack Drive, Annapolis, MD 21401
14 miles from Chester
Enter Dates
From $95
Check In 15 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
Most Recent HotelGuides 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 "
"A pleasant experience. The hotel staff was courteous and helpful.2015-06-30 "
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TripAdvisor Traveler Rating: Based on 1024 reviews
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14 miles
SpringHill Suites by Marriott Annapolis
189 Admiral Cochrane Drive, Annapolis, MD 21401
14 miles from Chester
Enter Dates
From $118
Check In 1500 Check Out 1200
Rated Very High
Upscale, smoke-free, all-suite hotel Located near Annapolis Mall Heated indoor swimming pool - exercise room Free hot breakfast buffet Free WiFi Free parking
Not pet friendly
- no pets allowed. - Aug 2016
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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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TripAdvisor Traveler Rating: Based on 719 reviews
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Chester Group Hotel Rates Hotels near Me
Hotels near Red Eye's Dock Bar 2.3 miles eastHotels near Chesapeake Bay Beach Club 2.4 miles westHotels near Jetty Dock Bar 2.6 miles eastHotels near Bay Bridge MD 4.3 miles westHotels near Sandy Point State Park 7 miles NWHotels near Queenstown Premium Outlets 7 miles eastHotels near Naval Support Activity Annapolis 10 miles westHotels near Chesapeake Bay MD 10 miles SWHotels near Aspen Wye River Conference Center 10 miles SEHotels near USNA – Naval Academy 10 miles westHotels near Annapolis Harbor 11 miles westHotels near Annapolis City Dock 11 miles westHotels near Annapolis Boat Show 11 miles westHotels near US Naval Academy Museum 11 miles westHotels near Annapolis Waterfront 11 miles westStevensville MD Hotels 1.4 miles westKent Narrows MD Hotels 2.8 miles eastKent Island MD Hotels 3.4 miles SWGrasonville MD Hotels 4.2 miles eastQueenstown MD Hotels 7 miles eastChesapeake Bay MD Hotels 10 miles SWCape St Claire MD Hotels 10 miles NWAnnapolis MD Hotels 11 miles westRock Hall MD Hotels 11 miles northWye Mills MD Hotels 11 miles eastArnold MD Hotels 12 miles westCentreville MD Hotels 13 miles eastSt Michaels MD Hotels 14 miles southLake Shore MD Hotels 14 miles NWLondontown MD Hotels 15 miles west
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.
To us, motels are smaller lodgings that have rooms you can enter directly from the parking area.hotels , on the other hand, you can enter your room only through a hall inside the building.
