Hotels in Chester
Free cancellation options if plans change
Earn rewards on every night you stay
Save more with Member Prices
Check prices for these dates
Where to stay in Chester?
Kent Island Resort
Kent Island ResortStevensville
9.2 out of 10, Wonderful, (130 reviews)
The price is $118
$166 total
includes taxes & fees
Jan 19 - Jan 20
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach ClubStevensville
9.4 out of 10, Exceptional, (433 reviews)
- Experience luxury seaside charm at this boutique spa hotel in Stevensville.
The price is $156
$199 total
includes taxes & fees
Feb 1 - Feb 2
Best Western Kent Narrows Inn
Best Western Kent Narrows InnGrasonville
8.0 out of 10, Very Good, (1,001 reviews)
- Waterfront hotel with stunning sunset views and indoor pool near hiking trails.
The price is $83
$93 total
includes taxes & fees
Jan 25 - Jan 26
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
9.2 out of 10, Wonderful, (952 reviews)
- 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 25 - Jan 26
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
9.6 out of 10, Exceptional, (702 reviews)
- Unwind along the Eastern Shore with waterfront views and indoor pool access.
The price is $129
$143 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, (1,002 reviews)
- Waterfront hotel with an indoor pool, where stunning bay views greet you every day.
The price is $122
$136 total
includes taxes & fees
Jan 25 - Jan 26
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
7.8 out of 10, Good, (867 reviews)
- A peaceful stay near Chesapeake Bay with free breakfast and outdoor pool.
The price is $86
$96 total
includes taxes & fees
Jan 19 - Jan 20
Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
10.0 out of 10, Exceptional, (59 reviews)
- 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 23 - Jan 24
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis DowntownAnnapolis
8.6 out of 10, Excellent, (1,000 reviews)
- Centrally located hotel near U.S. Naval Academy with Art Deco design and fitness.
The price is $89
$102 total
includes taxes & fees
Feb 9 - Feb 10
Historic Inns of Annapolis
Historic Inns of AnnapolisHistoric District
9.0 out of 10, Wonderful, (1,892 reviews)
- Downtown charm steps from the U.S. Naval Academy in historic Annapolis.
The price is $149
$204 total
includes taxes & fees
Jan 18 - Jan 19
Flag House Inn
Flag House InnHistoric District
9.4 out of 10, Exceptional, (85 reviews)
- Experience historic charm in the heart of Annapolis near the U.S. Naval Academy.
The price is $182
$207 total
includes taxes & fees
Jan 19 - Jan 20
Fairfield Inn & Suites By Marriott Annapolis
Fairfield Inn & Suites By Marriott AnnapolisAnnapolis
9.0 out of 10, Wonderful, (171 reviews)
- Stay near U.S. Naval Academy with free breakfast and 24-hour fitness center.
The price is $101
$115 total
includes taxes & fees
Jan 21 - Jan 22
Residence Inn By Marriott Annapolis
Residence Inn By Marriott AnnapolisAnnapolis
9.0 out of 10, Wonderful, (57 reviews)
- Enjoy a convenient stay near the Naval Academy with free breakfast daily.
The price is $127
$145 total
includes taxes & fees
Jan 21 - Jan 22
The Westin Annapolis
The Westin AnnapolisAnnapolis
8.8 out of 10, Excellent, (1,003 reviews)
- Luxurious spa escape near U.S. Naval Academy with attentive service.
The price is $149
$170 total
includes taxes & fees
Jan 18 - Jan 19
Graduate by Hilton Annapolis
Graduate by Hilton AnnapolisAnnapolis
9.4 out of 10, Exceptional, (1,001 reviews)
- Relaxing retreat minutes from U.S. Naval Academy with on-site Trophy Room dining.
The price is $147
$167 total
includes taxes & fees
Jan 25 - Jan 26
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph CollectionHistoric District
8.8 out of 10, Excellent, (898 reviews)
- Savor the harbor views and rooftop terrace in walkable downtown Annapolis.
The price is $186
$212 total
includes taxes & fees
Jan 25 - Jan 26
86 State Circle - Luxury Boutique Hotel
86 State Circle - Luxury Boutique HotelHistoric District
10.0 out of 10, Exceptional, (3 reviews)
- Discover historic Annapolis from this boutique hotel near the U.S. Naval Academy.
The price is $295
$336 total
includes taxes & fees
Jan 20 - Jan 21
George Brooks House B&B
George Brooks House B&BSt. Michaels
8.8 out of 10, Excellent, (66 reviews)
- Victorian charm just steps from St. Michaels attractions with outdoor pool.
The price is $170
$187 total
includes taxes & fees
Jan 19 - Jan 20
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique HotelAnnapolis
9.8 out of 10, Exceptional, (34 reviews)
- Experience historic charm in Maryland's capital just steps from the U.S. Naval Academy.
The price is $370
$422 total
includes taxes & fees
Feb 16 - Feb 17
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel AnnapolisAnnapolis
8.6 out of 10, Excellent, (1,001 reviews)
- Contemporary hotel near U.S. Naval Academy with fitness center and garden.
The price is $75
$85 total
includes taxes & fees
Feb 8 - Feb 9
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
Family friendly
Pet friendly
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
Historic Inns of Annapolis
10/10 Excellent
