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, (129)
9.2/10
Wonderful
(129)
The price is $143
$143
$195 total
includes taxes & fees
Dec 23 - Dec 24
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, (938)
9.2/10
Wonderful
(938)
- 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
Dec 29 - Dec 30
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1002)
8.0/10
Very Good
(1002)
- Waterfront hotel with stunning sunset views and indoor pool near hiking trails.
The price is $83
$83
$93 total
includes taxes & fees
Dec 30 - Dec 31
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (678)
9.6/10
Exceptional
(678)
- Unwind along the Eastern Shore with waterfront views and indoor pool access.
The price is $110
$110
$122 total
includes taxes & fees
Dec 28 - Dec 29
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, (432)
9.4/10
Exceptional
(432)
- Experience luxury seaside charm at this boutique spa hotel in Stevensville.
The price is $165
$165
$209 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1003)
9.0/10
Wonderful
(1003)
- Waterfront hotel with an indoor pool, where stunning bay views greet you every day.
The price is $114
$114
$127 total
includes taxes & fees
Dec 28 - Dec 29
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (863)
7.8/10
Good
(863)
- A peaceful stay near Chesapeake Bay with free breakfast and outdoor pool.
The price is $85
$85
$94 total
includes taxes & fees
Dec 28 - Dec 29
Inn at Huntingfield Creek
Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (58)
10/10
Exceptional
(58)
- 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 1 - Jan 2, 2026
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1906)
9.0/10
Wonderful
(1906)
- Downtown charm steps from the U.S. Naval Academy in historic Annapolis.
The price is $134
$134
$187 total
includes taxes & fees
Dec 28 - Dec 29
Graduate by Hilton Annapolis
Graduate by Hilton Annapolis
4.0 star property
Annapolis
9.4 out of 10, Exceptional, (1001)
9.4/10
Exceptional
(1001)
- Relaxing retreat minutes from U.S. Naval Academy with on-site Trophy Room dining.
The price is $135
$135
$154 total
includes taxes & fees
Dec 29 - Dec 30
Fairfield Inn & Suites By Marriott Annapolis
Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (167)
9.0/10
Wonderful
(167)
- Stay near U.S. Naval Academy with free breakfast and 24-hour fitness center.
The price is $110
$110
$125 total
includes taxes & fees
Dec 28 - Dec 29
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1003)
8.6/10
Excellent
(1003)
- Centrally located hotel near U.S. Naval Academy with Art Deco design and fitness.
The price is $89
$89
$102 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Residence Inn By Marriott Annapolis
Residence Inn By Marriott Annapolis
3.0 star property
Annapolis
8.8 out of 10, Excellent, (56)
8.8/10
Excellent
(56)
- Enjoy a convenient stay near the Naval Academy with free breakfast daily.
The price is $127
$127
$144 total
includes taxes & fees
Dec 28 - Dec 29
The Westin Annapolis
The Westin Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1001)
8.6/10
Excellent
(1001)
- Luxurious spa escape near U.S. Naval Academy with attentive service.
The price is $139
$139
$158 total
includes taxes & fees
Dec 23 - Dec 24
Flag House Inn
Flag House Inn
3.5 star property
Historic District
9.4 out of 10, Exceptional, (84)
9.4/10
Exceptional
(84)
- Experience historic charm in the heart of Annapolis near the U.S. Naval Academy.
The price is $183
$183
$208 total
includes taxes & fees
Dec 23 - Dec 24
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 $350
$350
$399 total
includes taxes & fees
Dec 23 - Dec 24
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (886)
8.8/10
Excellent
(886)
- Savor the harbor views and rooftop terrace in walkable downtown Annapolis.
The price is $195
$195
$222 total
includes taxes & fees
Dec 29 - Dec 30
George Brooks House B&B
George Brooks House B&B
3.0 star property
St. Michaels
8.6 out of 10, Excellent, (65)
8.6/10
Excellent
(65)
- Victorian charm just steps from St. Michaels attractions with outdoor pool.
The price is $153
$153
$168 total
includes taxes & fees
Jan 1 - Jan 2, 2026
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, (1001)
8.2/10
Very Good
(1001)
- Experience Annapolis with effortless access to Naval Academy and local dining spots.
The price is $80
$80
$91 total
includes taxes & fees
Jan 10 - Jan 11, 2026
1313 West Luxury Boutique Hotel
1313 West Luxury Boutique Hotel
2.0 star property
Homewood
- Elegant boutique hotel in Annapolis, just minutes from the U.S. Naval Academy.
The price is $399
$399
$455 total
includes taxes & fees
Jan 1 - Jan 2, 2026
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
7.8 out of 10, Good, (1003)
7.8/10
Good
(1003)
The price is $67
$67
$76 total
includes taxes & fees
Jan 10 - Jan 11, 2026
7.0 out of 10, Good, (409)
7.0/10
Good
(409)
The price is $70
$70
$80 total
includes taxes & fees
Dec 23 - Dec 24
8.2 out of 10, Very Good, (1001)
8.2/10
Very Good
(1001)
The price is $74
$74
$85 total
includes taxes & fees
Jan 2 - Jan 3, 2026
8.6 out of 10, Excellent, (1015)
8.6/10
Excellent
(1015)
The price is $75
$75
$85 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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, (1001)
8.2/10
Very Good
(1001)
The price is $80
$80
$91 total
includes taxes & fees
Jan 10 - Jan 11, 2026
7.6 out of 10, Good, (827)
7.6/10
Good
(827)
The price is $81
$81
$89 total
includes taxes & fees
Dec 28 - Dec 29
8.0 out of 10, Very Good, (1002)
8.0/10
Very Good
(1002)
The price is $83
$83
$93 total
includes taxes & fees
Dec 30 - Dec 31
8.6 out of 10, Excellent, (1002)
8.6/10
Excellent
(1002)
The price is $84
$84
$96 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island2.5 star property
Grasonville
7.8 out of 10, Good, (863)
7.8/10
Good
(863)
The price is $85
$85
$94 total
includes taxes & fees
Dec 28 - Dec 29
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, (938)
9.2/10
Wonderful
(938)
The price is $87
$87
$97 total
includes taxes & fees
Dec 29 - Dec 30
8.8 out of 10, Excellent, (181)
8.8/10
Excellent
(181)
The price is $88
$88
$100 total
includes taxes & fees
Jan 4 - Jan 5, 2026
8.6 out of 10, Excellent, (1003)
8.6/10
Excellent
(1003)
The price is $89
$89
$102 total
includes taxes & fees
Jan 4 - Jan 5, 2026
8.2 out of 10, Very Good, (1003)
8.2/10
Very Good
(1003)
The price is $89
$89
$102 total
includes taxes & fees
Dec 28 - Dec 29
8.8 out of 10, Excellent, (966)
8.8/10
Excellent
(966)
The price is $92
$92
$105 total
includes taxes & fees
Jan 11 - Jan 12, 2026
TownePlace Suites by Marriott Annapolis
TownePlace Suites by Marriott Annapolis3.0 star property
Annapolis
9.4 out of 10, Exceptional, (51)
9.4/10
Exceptional
(51)
The price is $93
$93
$106 total
includes taxes & fees
Jan 11 - Jan 12, 2026
8.2 out of 10, Very Good, (1001)
8.2/10
Very Good
(1001)
The price is $101
$101
$111 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1005)
9.0/10
Wonderful
(1005)
The price is $99
$99
$113 total
includes taxes & fees
Jan 11 - Jan 12, 2026
SpringHill Suites by Marriott Annapolis
SpringHill Suites by Marriott Annapolis3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1004)
9.0/10
Wonderful
(1004)
The price is $101
$101
$115 total
includes taxes & fees
Dec 28 - Dec 29
8.8 out of 10, Excellent, (1004)
8.8/10
Excellent
(1004)
The price is $105
$105
$120 total
includes taxes & fees
Jan 3 - Jan 4, 2026
9.0 out of 10, Wonderful, (1906)
9.0/10
Wonderful
(1906)
The price is $134
$134
$187 total
includes taxes & fees
Dec 28 - Dec 29
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
Pet friendly
Family 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
Historic Inns of Annapolis
10/10 Excellent
"Although expensive, great option for pets. Valet service and check-in/out were easy as well. There needs to be a sign on the outdoor valet podium stating if valet isnt present to bring keys inside to front desk. "
DoubleTree by Hilton Hotel Annapolis
10/10 Excellent
"Rooms were comfy, clean, quiet, and modern. The TV was nice and large, and any time we needed maintenance, they came up right away. The thing that stood out the most though was the front desk staff. They were super friendly, personable, amiable, and accomidating. I highly recommend staying here."
Best Western Annapolis
10/10 Excellent
"We've stayed at this hotel at least 20 times, despite being in the corner, in the back near the highway, we've found that the rooms are consistently clean and cozy. In the summer, the pool is awesome. And the breakfast is great.
We'll be back"
SpringHill Suites by Marriott Annapolis
10/10 Excellent
"Decent stay. Decent rooms for the $$. Charging for parking when the property in not in downtown Annapolis and in the middle of a commercial office complex is a $$ grab. "
Hyatt Place Kent Narrows & Marina
10/10 Excellent
"Clean, friendly and "
Hilton Garden Inn Annapolis Downtown
10/10 Excellent
"The room was very clean and comfortable, the staff was super friendly in helping make suggestions, i really appreciated their willingness to engage and help"
Courtyard by Marriott Annapolis
10/10 Excellent
"We keep coming back to the hotel with every visit to Annapolis. "
Country Inn & Suites by Radisson, Annapolis, MD
10/10 Excellent
"It was clean, quiet and comfortable. Will definitely come back if in the area again."
Hilton Garden Inn Kent Island Marina
10/10 Excellent
"Clean and friendly staff"
Frequently asked questions
What accommodations do travelers recommend in Chester?
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.