Hotels in Chester
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Aug 9 - Aug 10Tomorrow
Aug 10 - Aug 11Next weekend
Aug 14 - Aug 16In two weeks
Aug 21 - Aug 23Where to stay in Chester?
Laurel Grove Inn on the South
Laurel Grove Inn on the SouthAnnapolis
$180
$205 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
$119
$132 total
includes taxes & fees
Sep 7 - Sep 8
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
$163
$181 total
includes taxes & fees
Sep 8 - Sep 9
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
$147
$163 total
includes taxes & fees
Aug 16 - Aug 17
Best Western Kent Narrows Inn
Best Western Kent Narrows InnGrasonville
$115
$128 total
includes taxes & fees
Sep 7 - Sep 8
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
$100
$111 total
includes taxes & fees
Sep 7 - Sep 8
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach ClubStevensville
$216
$265 total
includes taxes & fees
Aug 31 - Sep 1
Kent Island Resort
Kent Island ResortStevensville
$162
$214 total
includes taxes & fees
Sep 7 - Sep 8
St Michaels Inn
St Michaels InnSt. Michaels
$99
$109 total
includes taxes & fees
Aug 31 - Sep 1
Village Inn Annapolis MD
Village Inn Annapolis MDAnnapolis
$83
$95 total
includes taxes & fees
Aug 10 - Aug 11
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MDAnnapolis
$91
$104 total
includes taxes & fees
Aug 30 - Aug 31
Best Western Plus Easton Inn & Suites
Best Western Plus Easton Inn & SuitesEaston
$139
$153 total
includes taxes & fees
Aug 10 - Aug 11
Historic Inns of Annapolis
Historic Inns of AnnapolisHistoric District
$102
$150 total
includes taxes & fees
Aug 16 - Aug 17
Hilton Garden Inn Annapolis
Hilton Garden Inn AnnapolisAnnapolis
$98
$111 total
includes taxes & fees
Aug 25 - Aug 26
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel AnnapolisAnnapolis
$98
$111 total
includes taxes & fees
Aug 30 - Aug 31
Best Western Annapolis
Best Western AnnapolisAnnapolis
$86
$97 total
includes taxes & fees
Aug 11 - Aug 12
Holiday Inn Express & Suites Annapolis by IHG
Holiday Inn Express & Suites Annapolis by IHGAnnapolis
$101
$115 total
includes taxes & fees
Aug 18 - Aug 19
Crowne Plaza Annapolis by IHG
Crowne Plaza Annapolis by IHGAnnapolis
$110
$125 total
includes taxes & fees
Sep 1 - Sep 2
Candlewood Suites Annapolis by IHG
Candlewood Suites Annapolis by IHGAnnapolis
$98
$117 total
includes taxes & fees
Aug 16 - Aug 17
Go beyond your typical stay in Chester
Pet friendly
Family friendly
Cottage
Top landmarks in Chester
Chesapeake Exploration Center
Chesapeake Exploration Center is worth a visit, located 0.8 mi (1.4 km) from central Kent Narrows.
Learn more about Chester
The region around Chester is home to attractions such as Chesapeake Exploration Center and Northern Chesapeake Bay.
See all hotels in Chester
Photo by Patricia Knorr
Check out reviews of Chester hotels guests love
Historic Inns of Annapolis
8/10 Good
"For tall(6'2") men bathroom amenities were a tight fit. Decor very nice."
Hilton Garden Inn Kent Island Marina
8/10 Good
"The location was great and the staff was courteous and helpful. My wife and I were celebrating our fourth wedding anniversary and had reserved a room with a king sized bed. We were given 2 queen size beds, I am 6’6”tall and had to sleep on an angel.They did not tell us that at check in. We were switched to a king bed the next day. You only have one chance to make a great first impression."
St Michaels Inn
10/10 Excellent
"Great locally owned spot- staff was wonderful. Room was spotless and recently renovated. The clientele was good, breakfast was better. They are mid-renovation with some repairs but make an effort to keep it accessible. Highly suggested."
Sonesta ES Suites Annapolis
10/10 Excellent
"The staff was great and the breakfast was even better. Would definitely book again"
DoubleTree by Hilton Hotel Annapolis
10/10 Excellent
"It was a great stay but I was charged for something and never explained. Have no idea what it was. Never asked for any extras or purchased anything from the front desk yet paid an extra 40$ smh check your receipts!"
Country Inn & Suites by Radisson, Annapolis, MD
10/10 Excellent
"friendly and polite staff. hotel was clean and quiet. parking was adequate. the one negative is that about half of the outlets in the room didn't actually work, so had to mess around finding which ones would charge devices."
The Tidewater Inn
8/10 Good
"Very helpful"
Holiday Inn Express & Suites Annapolis by IHG
8/10 Good
"I enjoyed my stay here. The staff was actually very friendly. There was a mishap with the elevator and it was down. The hotel is being maintained but it is dated and a bit shabby. There were stains on the carpets and on the bathroom fixtures. I know the pricing is because of the location but it’s not actually worth it."
Courtyard by Marriott Annapolis
10/10 Excellent
"I don’t really have anything except just know when breakfast time is so you can plan ahead."