Photo by Patricia Knorr
Hotels in Chester
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Kent Island Resort
Kent Island ResortStevensville
9.2 out of 10, Wonderful, (130)
The price is $127
$176 total
includes taxes & fees
Jan 11 - Jan 12
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach ClubStevensville
9.4 out of 10, Exceptional, (433)
- Experience luxury seaside charm at this boutique spa hotel in Stevensville.
The price is $156
$199 total
includes taxes & fees
Feb 1 - Feb 2
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
9.2 out of 10, Wonderful, (947)
- Escape to scenic Kent Island where bay views and bike trails await your morning coffee.
The price is $95
$105 total
includes taxes & fees
Jan 19 - Jan 20
Best Western Kent Narrows Inn
Best Western Kent Narrows InnGrasonville
8.0 out of 10, Very Good, (1000)
- Waterfront hotel with stunning sunset views and indoor pool near hiking trails.
The price is $83
$93 total
includes taxes & fees
Jan 14 - Jan 15
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
9.6 out of 10, Exceptional, (695)
- Unwind along the Eastern Shore with waterfront views and indoor pool access.
The price is $116
$129 total
includes taxes & fees
Jan 19 - Jan 20
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
9.0 out of 10, Wonderful, (1001)
- Waterfront hotel with an indoor pool, where stunning bay views greet you every day.
The price is $122
$136 total
includes taxes & fees
Jan 12 - Jan 13
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
7.8 out of 10, Good, (865)
- A peaceful stay near Chesapeake Bay with free breakfast and outdoor pool.
The price is $84
$93 total
includes taxes & fees
Jan 19 - Jan 20
Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
10.0 out of 10, Exceptional, (59)
- Serene B&B on Chesapeake Bay offers outdoor pool and spa treatments in Rock Hall.
The price is $156
$173 total
includes taxes & fees
Jan 11 - Jan 12
Historic Inns of Annapolis
Historic Inns of AnnapolisHistoric District
9.0 out of 10, Wonderful, (1885)
- Downtown charm steps from the U.S. Naval Academy in historic Annapolis.
The price is $139
$193 total
includes taxes & fees
Jan 11 - Jan 12
Residence Inn By Marriott Annapolis
Residence Inn By Marriott AnnapolisAnnapolis
9.0 out of 10, Wonderful, (57)
- Enjoy a convenient stay near the Naval Academy with free breakfast daily.
The price is $127
$145 total
includes taxes & fees
Jan 12 - Jan 13
Fairfield Inn & Suites By Marriott Annapolis
Fairfield Inn & Suites By Marriott AnnapolisAnnapolis
9.0 out of 10, Wonderful, (170)
- Stay near U.S. Naval Academy with free breakfast and 24-hour fitness center.
The price is $110
$125 total
includes taxes & fees
Jan 12 - Jan 13
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis DowntownAnnapolis
8.6 out of 10, Excellent, (1009)
- Centrally located hotel near U.S. Naval Academy with Art Deco design and fitness.
The price is $90
$102 total
includes taxes & fees
Feb 8 - Feb 9
The Westin Annapolis
The Westin AnnapolisAnnapolis
8.6 out of 10, Excellent, (1000)
- Luxurious spa escape near U.S. Naval Academy with attentive service.
The price is $127
$144 total
includes taxes & fees
Jan 11 - Jan 12
Graduate by Hilton Annapolis
Graduate by Hilton AnnapolisAnnapolis
9.4 out of 10, Exceptional, (1004)
- Relaxing retreat minutes from U.S. Naval Academy with on-site Trophy Room dining.
The price is $147
$167 total
includes taxes & fees
Jan 15 - Jan 16
Flag House Inn
Flag House InnHistoric District
9.4 out of 10, Exceptional, (85)
- Experience historic charm in the heart of Annapolis near the U.S. Naval Academy.
The price is $182
$207 total
includes taxes & fees
Jan 11 - Jan 12
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique HotelAnnapolis
9.8 out of 10, Exceptional, (34)
- Experience historic charm in Maryland's capital just steps from the U.S. Naval Academy.
The price is $206
$234 total
includes taxes & fees
Jan 11 - Jan 12
86 State Circle - Luxury Boutique Hotel
86 State Circle - Luxury Boutique HotelHistoric District
10.0 out of 10, Exceptional, (3)
- Discover historic Annapolis from this boutique hotel near the U.S. Naval Academy.
The price is $295
$336 total
includes taxes & fees
Jan 11 - Jan 12
George Brooks House B&B
George Brooks House B&BSt. Michaels
8.8 out of 10, Excellent, (66)
- Victorian charm just steps from St. Michaels attractions with outdoor pool.
The price is $170
$187 total
includes taxes & fees
Jan 12 - Jan 13
Holiday Inn Express & Suites Annapolis by IHG
Holiday Inn Express & Suites Annapolis by IHGAnnapolis
8.2 out of 10, Very Good, (1000)
- Experience Annapolis with effortless access to Naval Academy and local dining spots.
The price is $93
$106 total
includes taxes & fees
Jan 10 - Jan 11
Crowne Plaza Annapolis by IHG
Crowne Plaza Annapolis by IHGAnnapolis
8.8 out of 10, Excellent, (1019)
- Central location near shopping malls, with a relaxing indoor pool and welcoming staff.
The price is $106
$121 total
includes taxes & fees
Feb 6 - Feb 7
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.
Budget hotels in Chester and vicinity
7.0 out of 10, Good, (410)
The price is $70
$80 total
includes taxes & fees
Jan 10 - Jan 11
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.
Go beyond your typical stay in Chester
Top landmarks in Chester
Learn more about Chester
The region around Chester is home to attractions such as Chesapeake Exploration Center and Northern Chesapeake Bay.
Photo by Patricia Knorr
Open Photo by Patricia Knorr
Check out reviews of Chester hotels guests love
Hampton Inn & Suites Annapolis
10/10 Excellent
