Photo by Patricia Knorr
Hotels in Chester
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Where to stay in Chester?
Kent Island Resort
Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130)
9.2/10
Wonderful
(130)
The price is $127
$127
$176 total
includes taxes & fees
Jan 11 - Jan 12
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (433)
9.4/10
Exceptional
(433)
- Experience luxury seaside charm at this boutique spa hotel in Stevensville.
The price is $156
$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 IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (947)
9.2/10
Wonderful
(947)
- Escape to scenic Kent Island where bay views and bike trails await your morning coffee.
The price is $87
$87
$97 total
includes taxes & fees
Jan 19 - Jan 20
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1000)
8.0/10
Very Good
(1000)
- Waterfront hotel with stunning sunset views and indoor pool near hiking trails.
The price is $83
$83
$93 total
includes taxes & fees
Jan 14 - Jan 15
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (695)
9.6/10
Exceptional
(695)
- Unwind along the Eastern Shore with waterfront views and indoor pool access.
The price is $116
$116
$129 total
includes taxes & fees
Jan 19 - Jan 20
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1000)
9.0/10
Wonderful
(1000)
- Waterfront hotel with an indoor pool, where stunning bay views greet you every day.
The price is $122
$122
$136 total
includes taxes & fees
Jan 11 - Jan 12
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (864)
7.8/10
Good
(864)
- A peaceful stay near Chesapeake Bay with free breakfast and outdoor pool.
The price is $84
$84
$93 total
includes taxes & fees
Jan 19 - Jan 20
Inn at Huntingfield Creek
Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (59)
10/10
Exceptional
(59)
- Serene B&B on Chesapeake Bay offers outdoor pool and spa treatments in Rock Hall.
The price is $156
$156
$173 total
includes taxes & fees
Jan 11 - Jan 12
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1911)
9.0/10
Wonderful
(1911)
- Downtown charm steps from the U.S. Naval Academy in historic Annapolis.
The price is $139
$139
$193 total
includes taxes & fees
Jan 8 - Jan 9
Residence Inn By Marriott Annapolis
Residence Inn By Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (57)
9.0/10
Wonderful
(57)
- Enjoy a convenient stay near the Naval Academy with free breakfast daily.
The price is $127
$127
$145 total
includes taxes & fees
Jan 12 - Jan 13
Fairfield Inn & Suites By Marriott Annapolis
Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (170)
9.0/10
Wonderful
(170)
- Stay near U.S. Naval Academy with free breakfast and 24-hour fitness center.
The price is $110
$110
$125 total
includes taxes & fees
Jan 12 - Jan 13
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1009)
8.6/10
Excellent
(1009)
- Centrally located hotel near U.S. Naval Academy with Art Deco design and fitness.
The price is $91
$91
$104 total
includes taxes & fees
Jan 11 - Jan 12
The Westin Annapolis
The Westin Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1000)
8.6/10
Excellent
(1000)
- Luxurious spa escape near U.S. Naval Academy with attentive service.
The price is $127
$127
$144 total
includes taxes & fees
Jan 8 - Jan 9
Graduate by Hilton Annapolis
Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1004)
9.4/10
Exceptional
(1004)
- Relaxing retreat minutes from U.S. Naval Academy with on-site Trophy Room dining.
The price is $147
$147
$167 total
includes taxes & fees
Jan 15 - Jan 16
Flag House Inn
Flag House Inn
3.5 star property
Historic District
9.4 out of 10, Exceptional, (85)
9.4/10
Exceptional
(85)
- Experience historic charm in the heart of Annapolis near the U.S. Naval Academy.
The price is $182
$182
$207 total
includes taxes & fees
Jan 11 - Jan 12
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
9.8 out of 10, Exceptional, (34)
9.8/10
Exceptional
(34)
- Experience historic charm in Maryland's capital just steps from the U.S. Naval Academy.
The price is $206
$206
$234 total
includes taxes & fees
Jan 11 - Jan 12
86 State Circle - Luxury Boutique Hotel
86 State Circle - Luxury Boutique Hotel
2.0 star property
Historic District
10.0 out of 10, Exceptional, (3)
10/10
Exceptional
(3)
- Discover historic Annapolis from this boutique hotel near the U.S. Naval Academy.
The price is $295
$295
$336 total
includes taxes & fees
Jan 11 - Jan 12
George Brooks House B&B
George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (66)
8.8/10
Excellent
(66)
- Victorian charm just steps from St. Michaels attractions with outdoor pool.
The price is $170
$170
$187 total
includes taxes & fees
Jan 8 - Jan 9
Holiday Inn Express & Suites Annapolis by IHG
Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
Annapolis
8.2 out of 10, Very Good, (1000)
8.2/10
Very Good
(1000)
- Experience Annapolis with effortless access to Naval Academy and local dining spots.
The price is $93
$93
$106 total
includes taxes & fees
Jan 10 - Jan 11
Crowne Plaza Annapolis by IHG
Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1019)
8.8/10
Excellent
(1019)
- Central location near shopping malls, with a relaxing indoor pool and welcoming staff.
The price is $106
$106
$121 total
includes taxes & fees
Feb 4 - Feb 5
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.
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)
7.0/10
Good
(410)
The price is $70
$70
$80 total
includes taxes & fees
Jan 8 - Jan 9
7.8 out of 10, Good, (1000)
7.8/10
Good
(1000)
The price is $72
$72
$82 total
includes taxes & fees
Jan 10 - Jan 11
8.2 out of 10, Very Good, (1000)
8.2/10
Very Good
(1000)
The price is $81
$81
$92 total
includes taxes & fees
Feb 1 - Feb 2
Holiday Inn Express & Suites Annapolis by IHG
Holiday Inn Express & Suites Annapolis by IHG2.5 star property
Annapolis
8.2 out of 10, Very Good, (1000)
8.2/10
Very Good
(1000)
The price is $93
$93
$106 total
includes taxes & fees
Jan 10 - Jan 11
8.0 out of 10, Very Good, (1000)
8.0/10
Very Good
(1000)
The price is $83
$83
$93 total
includes taxes & fees
Jan 14 - Jan 15
8.6 out of 10, Excellent, (1000)
8.6/10
Excellent
(1000)
The price is $83
$83
$94 total
includes taxes & fees
Jan 11 - Jan 12
8.6 out of 10, Excellent, (1000)
8.6/10
Excellent
(1000)
The price is $84
$84
$96 total
includes taxes & fees
Jan 25 - Jan 26
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island2.5 star property
Grasonville
7.8 out of 10, Good, (864)
7.8/10
Good
(864)
The price is $84
$84
$93 total
includes taxes & fees
Jan 19 - Jan 20
8.8 out of 10, Excellent, (188)
8.8/10
Excellent
(188)
The price is $84
$84
$96 total
includes taxes & fees
Jan 16 - Jan 17
7.6 out of 10, Good, (832)
7.6/10
Good
(832)
The price is $85
$85
$94 total
includes taxes & fees
Jan 14 - Jan 15
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG2.5 star property
Grasonville
9.2 out of 10, Wonderful, (947)
9.2/10
Wonderful
(947)
The price is $87
$87
$97 total
includes taxes & fees
Jan 19 - Jan 20
8.2 out of 10, Very Good, (1011)
8.2/10
Very Good
(1011)
The price is $89
$89
$102 total
includes taxes & fees
Jan 13 - Jan 14
8.8 out of 10, Excellent, (975)
8.8/10
Excellent
(975)
The price is $92
$92
$105 total
includes taxes & fees
Jan 26 - Jan 27
8.6 out of 10, Excellent, (1009)
8.6/10
Excellent
(1009)
The price is $91
$91
$104 total
includes taxes & fees
Jan 11 - Jan 12
8.2 out of 10, Very Good, (1000)
8.2/10
Very Good
(1000)
The price is $101
$101
$111 total
includes taxes & fees
Jan 11 - Jan 12
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1000)
9.0/10
Wonderful
(1000)
The price is $98
$98
$112 total
includes taxes & fees
Jan 13 - Jan 14
9.4 out of 10, Exceptional, (364)
9.4/10
Exceptional
(364)
The price is $100
$100
$110 total
includes taxes & fees
Jan 8 - Jan 9
TownePlace Suites by Marriott Annapolis
TownePlace Suites by Marriott Annapolis3.0 star property
Annapolis
9.4 out of 10, Exceptional, (53)
9.4/10
Exceptional
(53)
The price is $101
$101
$115 total
includes taxes & fees
Jan 18 - Jan 19
8.8 out of 10, Excellent, (1019)
8.8/10
Excellent
(1019)
The price is $106
$106
$121 total
includes taxes & fees
Feb 4 - Feb 5
SpringHill Suites by Marriott Annapolis
SpringHill Suites by Marriott Annapolis3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1000)
9.0/10
Wonderful
(1000)
The price is $110
$110
$125 total
includes taxes & fees
Jan 12 - Jan 13
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.
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
Cottage
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
Hyatt Place Kent Narrows & Marina
10/10 Excellent
"Clean Room,Accomodating and Pleasant Staff"
Country Inn & Suites by Radisson, Annapolis, MD
10/10 Excellent
"No hot water for the entire first night. Had plans for the night but could not take shower. Not a good experience. Other than that, everything was fine."
Sonesta ES Suites Annapolis
10/10 Excellent
"Staff was extremely friendly and helpful. Breakfast was delicious. Hotel was very clean and comfortable. We loved our room. Kitchen very useful as we brought leftovers and were able to heat them up in room and didn't need to go out to restaurant. Very comfortable mattress. All in all an excellent stay."
The Westin Annapolis
10/10 Excellent
"We were able to get there an hour early and our room was ready and the staff were great!"
Crowne Plaza Annapolis by IHG
10/10 Excellent
"Amazing staff and breakfast was delicious. "
Historic Inns of Annapolis
10/10 Excellent
"Staff was exceptionally friendly & helpful. Room clean & tastefully appointed. Location was perfectly situated in the old town & near antique stores, Main Street & the harbor. Great getaway!"
Best Western Annapolis
10/10 Excellent
"Great hospitality and breakfast was good…"
DoubleTree by Hilton Hotel Annapolis
10/10 Excellent
"The room was excellent, and the staff was as well. Special kudos to Jody behind the desk. The hotel bar
/restaurant is fantastic and the bartender, Carlos, was amazing! We had a great time in the bar ringing in the new year. "
Courtyard by Marriott Annapolis
10/10 Excellent
" Clean room
"
Frequently asked questions
What accommodations do travelers recommend in Chester?
Guests like Hyatt Place Kent Narrows & Marina.
Can I book a refundable accommodation in Chester?
If you're looking for the flexibility to change your travel plans to Chester, most properties provide refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow down the results.
Where can I stay in Chester if I want a vacation rental instead of a traditional hotel?
If you want to find a good alternative to a hotel, review our selection of 10 vacation homes.
What will the weather in Chester be like during my visit?
July and August are typically the warmest months in Chester when the average temp is 74°F. January and February are the coldest months when the average temperature is 39°F. July and October are the months with the most rain.
Why should I book my Chester hotel through Hotels.com?
There are lots of reasons to book your Chester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.