Book Cheap Hotels in Chester
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Check hotel availability in Chester
Most frequently booked Chester hotels

Historic Inns of Annapolis
58 State Circle, Annapolis, MD
17.34 km from city centre
The price is CA $150 per night
CA $150
CA $218 total
includes taxes & fees
30 Mar - 31 Mar
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions The Colonial Players and 97, 99 and 101 East Street are located nearby.
Pet-friendly
Free WiFi

DoubleTree by Hilton Hotel Annapolis
210 Holiday Court, Annapolis, MD
Free cancellation
Reserve now, pay when you stay
22.18 km from city centre
The price is CA $137 per night
CA $137
CA $156 total
includes taxes & fees
25 Mar - 26 Mar
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Annapolis Harbor Center Shopping Center and Annapolis Mall Shopping Center are located nearby.
Pet-friendly
Parking included

Country Inn & Suites by Radisson, Annapolis, MD
2600 Housley Road, Annapolis, MD
Free cancellation
23.1 km from city centre
The price is CA $127 per night
CA $127
CA $145 total
includes taxes & fees
23 Mar - 24 Mar
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Annapolis Bowl and Annapolis Mall Shopping Center are located nearby.
Pool
Hot tub

Hilton Garden Inn Annapolis Downtown
174 West Street, Annapolis, MD
Free cancellation
Reserve now, pay when you stay
18.24 km from city centre
The price is CA $133 per night
CA $133
CA $152 total
includes taxes & fees
3 Apr - 4 Apr
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chesapeake Bay Bridge and Annapolis Civil Rights Plaque are located nearby.
Pet-friendly
Free WiFi

Graduate by Hilton Annapolis
126 West St, Annapolis, MD
Free cancellation
Reserve now, pay when you stay
18.04 km from city centre
The price is CA $242 per night
CA $242
CA $276 total
includes taxes & fees
16 Apr - 17 Apr
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Annapolis Civil Rights Plaque and Asbury United Methodist Church are located nearby.
Pet-friendly
Free WiFi

Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St, Annapolis, MD
Free cancellation
Reserve now, pay when you stay
17.01 km from city centre
The price is CA $296 per night
CA $296
CA $338 total
includes taxes & fees
31 Mar - 1 Apr
Stay at this 4-star eco-certified hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Ego Alley and Kunta Kinte Plaque & Alex Haley Memorial are located nearby.
Pet-friendly
Free WiFi

The Westin Annapolis
100 Westgate Cir, Annapolis, MD
Free cancellation
Reserve now, pay when you stay
18.57 km from city centre
The price is CA $185 per night
CA $185
CA $211 total
includes taxes & fees
19 Mar - 20 Mar
Stay at this 4-star spa hotel in Annapolis. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Maryland Hall for Creative Arts and Ballet Theater of Maryland are located nearby.
Pool
Spa

Crowne Plaza Annapolis by IHG
173 Jennifer Rd, Annapolis, MD
Free cancellation
22.02 km from city centre
The price is CA $139 per night
CA $139
CA $159 total
includes taxes & fees
24 Mar - 25 Mar
Stay at this 3.5-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Annapolis Mall Shopping Center and Westfield Annapolis Mall are located nearby.
Parking included
Free WiFi

SpringHill Suites by Marriott Annapolis
189 Admiral Cochrane Drive, Annapolis, MD
Free cancellation
Reserve now, pay when you stay
22.47 km from city centre
The price is CA $157 per night
CA $157
CA $179 total
includes taxes & fees
23 Mar - 24 Mar
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Annapolis Harbor Center Shopping Center and Annapolis Harbour Center are located nearby.
Pool
Hot tub
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.
Hotels in Chester with star rating
Check Chester hotel room prices by star rating

5 Star Hotels
3 properties
Top hotels in Chester for Extended Stay

Town View King Apartment with Private Beach - Walk to shops and restaurants
Oxford
10/10 Exceptional! (3 reviews)
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.
Chester hotels essential information
Accommodation | 1,202 hotels |
---|---|
Lowest Price | CA $127 |
Highest Price | CA $296 |
Popular hotels | Historic Inns of Annapolis, DoubleTree by Hilton Hotel Annapolis, Country Inn & Suites by Radisson, Annapolis, MD, Hilton Garden Inn Annapolis Downtown, Graduate by Hilton Annapolis, Annapolis Waterfront Hotel, Autograph Collection, The Westin Annapolis, Crowne Plaza Annapolis by IHG, SpringHill Suites by Marriott Annapolis |
Frequently asked questions
Recent Chester hotel reviews by fellow wanderers

Graduate by Hilton Annapolis
5 out of 5
Posted 23 hours ago
Travelocity Verified Review
"Graduate always does a great job. "
A verified traveller from Sun Valley stayed at Graduate by Hilton Annapolis
Types of hotels
Hotels near…
Hotels by star rating
Areas of Chester
Most popular
Hotels
Hotels in Palm SpringsHotels in Grand ForksHotels in Ocean CityHotels in Great FallsHotels in Palm DesertHotels in WoodbineHotels in WatertownHotels in FargoHotels in HonoluluHotels in DuluthAll Inclusive Resorts & Hotels in Myrtle BeachHotels in Niagara FallsHotels in BangorHotels in KalispellHotels in Burlington