Hotels in Chester
Search over 1,193 hotels from $115
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Top Rated Chester Hotels

Waterfront Sunset Bayview: sleeps 6
Chester MD
3.84 mi from city center
At this vacation home, guests have access to features like laundry facilities.
Kitchen
Washer

DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Free Cancellation
Reserve now, pay when you stay
13.77 mi from city center
$114 nightly
The price is $130 total per night
$130 total
May 3 - May 4
Total with taxes and fees
Guests of DoubleTree by Hilton Hotel Annapolis enjoy a 24-hour gym, free WiFi in public areas, and conference space. There's free parking and a free area shuttle. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry and luggage storage. Additional amenities include a business center, a microwave in a common area, and a refrigerator in a common area.
Pet friendly
Parking included

Historic Inns of Annapolis
58 State Circle Annapolis MD
Free Cancellation
Reserve now, pay when you stay
10.77 mi from city center
$189 nightly
The price is $215 total per night
$215 total
May 25 - May 26
Total with taxes and fees
At Historic Inns of Annapolis, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 50.00 per night, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with tours or tickets, luggage storage, and securing valuables. Other amenities at this historic hotel include conference space, coffee/tea in a common area, and express check-in.
Pet friendly
Free WiFi

Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Free Cancellation
13.68 mi from city center
$127 nightly
The price is $145 total per night
$145 total
May 3 - May 4
Total with taxes and fees
At Crowne Plaza Annapolis by IHG, guests enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. You can take advantage of free parking if you drive. The 24-hour front desk has staff standing by to help with luggage storage and dry cleaning/laundry. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Parking included

Country Inn & Suites by Radisson, Annapolis, MD
2600 Housley Road Annapolis MD
Free Cancellation
14.38 mi from city center
$101 nightly
The price is $115 total per night
$115 total
May 3 - May 4
Total with taxes and fees
At Country Inn & Suites by Radisson, Annapolis, MD, guests enjoy features like an indoor pool, a gym, and free WiFi in public areas. If you drive, take advantage of free parking. The 24-hour front desk has multilingual staff ready to assist with securing valuables and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include a hot tub, meeting rooms, and conference space.
Pool
Hot Tub

Courtyard by Marriott Annapolis
2559 Riva Rd Annapolis MD
Free Cancellation
Reserve now, pay when you stay
14.18 mi from city center
$110 nightly
The price is $125 total per night
$125 total
May 6 - May 7
Total with taxes and fees
At Courtyard by Marriott Annapolis, guests enjoy features like an indoor pool, a gym, and free WiFi in public areas. Self parking is available for USD 10 per day. Multilingual staff at the 24-hour front desk can assist with luggage storage, dry cleaning/laundry, and securing valuables. Additional amenities include a hot tub, conference space, and a 24-hour business center.
Pool
Hot Tub

Hilton Garden Inn Annapolis Downtown
174 West Street Annapolis MD
Free Cancellation
Reserve now, pay when you stay
11.32 mi from city center
$111 nightly
The price is $127 total per night
$127 total
May 3 - May 4
Total with taxes and fees
Hilton Garden Inn Annapolis Downtown features a 24-hour gym, free WiFi in public areas, and conference space. Parking is available for USD 35 per night (USD 39 per night for valet parking), and there's also an area shuttle. The front desk has multilingual staff on hand 24/7 to help with dry cleaning/laundry, luggage storage, and securing valuables. Additional amenities include a business center, laundry facilities, and an ATM.
Pet friendly
Free WiFi

Sonesta ES Suites Annapolis
170 Admiral Cochrane Dr Edgewater MD
Free Cancellation
Reserve now, pay when you stay
14.05 mi from city center
$101 nightly
The price is $115 total per night
$115 total
May 7 - May 8
Total with taxes and fees
Sonesta ES Suites Annapolis features a 24-hour gym, free WiFi in public areas, and a 24-hour business center. Self parking is offered for USD 7 per night. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and a meeting room.
Pool
Breakfast included

Graduate by Hilton Annapolis
126 West St Annapolis MD
Free Cancellation
Reserve now, pay when you stay
11.2 mi from city center
$162 nightly
The price is $185 total per night
$185 total
May 3 - May 4
Total with taxes and fees
Graduate by Hilton Annapolis features a 24-hour gym, free WiFi in public areas, and conference space. Valet parking is available for USD 39 per night. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include free use of bicycles, an ATM, and a ballroom.
Pet friendly
Free WiFi

The Westin Annapolis
100 Westgate Cir Annapolis MD
11.53 mi from city center
$179 nightly
The price is $204 total per night
$204 total
May 3 - May 4
Total with taxes and fees
At The Westin Annapolis, guests enjoy a full-service spa, an indoor pool, and a 24-hour gym. Valet parking is offered for USD 39 per night. Front-desk staff can answer questions 24/7, and assist with securing valuables, concierge services, and luggage storage. Other amenities at this spa hotel include free WiFi in public areas, conference space, and a 24-hour business center.
Pool
Spa

SpringHill Suites by Marriott Annapolis
189 Admiral Cochrane Drive Annapolis MD
Free Cancellation
Reserve now, pay when you stay
13.96 mi from city center
$114 nightly
The price is $129 total per night
$129 total
May 3 - May 4
Total with taxes and fees
At SpringHill Suites by Marriott Annapolis, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. Self parking is offered for USD 10.00 per day. Front-desk staff can answer questions 24/7, and assist with luggage storage, securing valuables, and concierge services. Additional amenities include a hot tub, conference space, and a 24-hour business center.
Pool
Hot Tub

Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
10.53 mi from city center
$229 nightly
The price is $261 total per night
$261 total
May 10 - May 11
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection offers a 24-hour gym, a rooftop terrace, and free WiFi in public areas. Valet parking is available for USD 39 per day. The 24-hour front desk has staff standing by to help with luggage storage, securing valuables, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include meeting rooms, conference space, and a 24-hour business center.
Pet friendly
Free WiFi
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.
What's the best place for a stay in Chester?
What are the best hotels in downtown Chester?
These are some of the most popular hotels in the center of Chester:
- Hyatt Place Kent Narrows & Marina is hotel has free WiFi, free parking, and a 24-hour fitness center.
- Best Western Kent Narrows Inn is hotel has free breakfast, free WiFi, and free parking.
- The Inn at Chesapeake Bay Beach Club is hotel has a full-service spa, free WiFi, and free parking.
Chester hotels essential information
Accommodation | 1,193 hotels |
|---|---|
Lowest Price | $115 |
Highest Price | $261 |
Popular hotels | Waterfront Sunset Bayview: sleeps 6, DoubleTree by Hilton Hotel Annapolis, Historic Inns of Annapolis, Crowne Plaza Annapolis by IHG, Country Inn & Suites by Radisson, Annapolis, MD, Courtyard by Marriott Annapolis, Hilton Garden Inn Annapolis Downtown, Sonesta ES Suites Annapolis, Graduate by Hilton Annapolis, The Westin Annapolis, SpringHill Suites by Marriott Annapolis, Annapolis Waterfront Hotel, Autograph Collection |
Recent Reviews

Country Inn & Suites by Radisson, Annapolis, MD
5/5 Excellent
"Beds were very comfortable and the shower was nice !"
A verified traveler stayed at Country Inn & Suites by Radisson, Annapolis, MD
Posted 10 hours ago
More to Explore
- Hotels near Annapolis City Dock
- B&B in Kent Narrows
- Business Hotels in Kent Narrows
- Hotels with Pool in Kent Narrows
- Hotels with a Gym in Kent Narrows
- Hotels with Room Service in Kent Narrows
- Pet Friendly Hotels in Kent Narrows
- Kent Narrows Hotels
- Hotels near Bay Hills Golf Club
- Hotels near U.S. Naval Academy Golf Club
- Gibson Island Hotels
- Hotels near Annapolis Maritime Museum
- Hotels near Maryland State House
- 2 Star Hotels in Kent Island
- 3 Star Hotels in Kent Island
- 5 Star Hotels in Kent Island
- Apartments in Kent Island
- Condo Rentals in Kent Island
- Kid Friendly Hotels in Kent Island
- Motels in Kent Island
- Villas in Kent Island
- Hotels near Queenstown Premium Outlets
- Hotels near Ego Alley
- Grasonville Hotels
- Hotels near Ferry Park
- Queenstown Hotels
- Hotels near William Paca House
- Hotels near Chesapeake Bay Bridge
- Hotels near Chesapeake Bay Environmental Center
- Hotels near Sandy Point State Park
- Hotels near Hammond-Harwood House
- Hotels near Banneker Douglass Museum
- Hotels near U.S. Naval Academy
- Hotels near Bay Bridge Market Place Shopping Center
- Hotels near Eastern Neck National Wildlife Refuge
- Farmstay in Stevensville
- Condo Rentals in Stevensville
- Cottages in Stevensville
- Extended Stay Hotels in Stevensville
- Beach Resorts & in Stevensville
- Best Western Hotels in Stevensville
- Fishing Resorts & in Stevensville
- Hotels with Balconies in Stevensville
- Pet Friendly Hotels in Stevensville
- Spa Resorts & in Stevensville
- Stevensville Hotels
- Houseboats in Stevensville
- Vacation Homes in Stevensville
- Annapolis Hotels
- Hotels near Queenstown Harbor Golf Club
- Hotels near Queenstown Harbor Golf Links
- Hotels near Annapolis Landing Marina
- Historic District Hotels
- Cape Saint Claire Hotels
- Hotels near St. John's College
- Maryland Hotels
- Flights to Kent Island
- Flights from Atlanta to Kent Island
- Flights from Boston to Kent Island
- Flights from New York to Kent Island
- Flights from Venice to Kent Island
- Flights from Hartford to Kent Island
- Flights from Kent Island
- Flights from Oakland to Kent Island
- Flights from Grand Rapids to Kent Island
- Flights from Asheville to Kent Island
- Flights from Guatemala City to Kent Island
- Flights from Atlanta to Stevensville
- Flights from Boston to Stevensville
- Flights from Charlotte to Stevensville
- Flights from Chicago to Stevensville
- Flights from Denver to Stevensville
- Flights from Houston to Stevensville
- Flights from Las Vegas to Stevensville
- Flights from Memphis to Stevensville
- Flights from Miami to Stevensville
- Flights from Minneapolis - St. Paul to Stevensville
- Flights from Nashville to Stevensville
- Flights from New Orleans to Stevensville
- Flights from Portland to Stevensville
- Flights from Seattle to Stevensville
- Flights from Shanghai to Stevensville
- Flights from Greensboro to Stevensville
- Flights from Oklahoma City to Stevensville
- Flights from Dayton to Stevensville
- Flights from Birmingham to Stevensville
- Flights from Tampa to Stevensville
- Flights from Bozeman to Stevensville
- Flights to Maryland



