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Cheap Chester Hotels

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Chester MD
1.9 mi from city center
Located in Chester, this vacation home is on the waterfront, within a 10-minute drive of Chesapeake Exploration Center and Island Dog Park.
Kitchen
Washer
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$144 nightly
The price is $164 total per night
$164 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
10.77 mi from city center
With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.
Pet friendly
Free WiFi
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
$123 nightly
The price is $141 total per night
$141 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
11.2 mi from city center
With a stay at Graduate by Hilton Annapolis, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Civil Rights Plaque.
Pet friendly
Free WiFi
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
$81 nightly
The price is $92 total per night
$92 total
Dec 28 - Dec 29
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.77 mi from city center
With a stay at DoubleTree by Hilton Hotel Annapolis in Annapolis, you'll be in the business district, within a 5-minute drive of U.S. Naval Academy and The Kunta Kinte Alex Haley Memorial.
Pet friendly
Parking included
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street Annapolis MD
$79 nightly
The price is $90 total per night
$90 total
Dec 28 - Dec 29
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
11.32 mi from city center
With a stay at Hilton Garden Inn Annapolis Downtown, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Civil Rights Plaque.
Pet friendly
Free WiFi
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
$97 nightly
The price is $111 total per night
$111 total
Dec 15 - Dec 16
Total with taxes and fees
Free Cancellation
13.68 mi from city center
Located in Annapolis, Crowne Plaza Annapolis by IHG is a 4-minute walk from Westfield Annapolis Mall and 14 minutes by foot from Anne Arundel Medical Center.
Pool
Parking included
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
$83 nightly
The price is $95 total per night
$95 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
14.05 mi from city center
With a stay at Sonesta ES Suites Annapolis in Edgewater, you'll be in the historical district, within a 10-minute drive of U.S. Naval Academy and Annapolis Harbour Center.
Pool
Breakfast included
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road Annapolis MD
$83 nightly
The price is $95 total per night
$95 total
Dec 28 - Dec 29
Total with taxes and fees
Free Cancellation
14.34 mi from city center
With a stay at Country Inn & Suites by Radisson, Annapolis, MD in Annapolis, you'll be in a shopping district, within a 10-minute drive of U.S. Naval Academy and Annapolis Mall Shopping Center.
Pool
Hot Tub
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
$178 nightly
The price is $203 total per night
$203 total
Dec 14 - Dec 15
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
10.57 mi from city center
With a stay at Annapolis Waterfront Hotel, Autograph Collection, you'll be centrally located in Annapolis, within a 10-minute walk of U.S. Naval Academy and William Paca House.
Pet friendly
Free WiFi
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir Annapolis MD
$154 nightly
The price is $176 total per night
$176 total
Dec 14 - Dec 15
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
11.53 mi from city center
With a stay at The Westin Annapolis in Annapolis, you'll be in the historical district, within a 5-minute drive of U.S. Naval Academy and People's Brewer Hill Cemetery.
Pool
Spa
Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

2.5 out of 5
1 Womack Dr Annapolis MD
$79 nightly
The price is $90 total per night
$90 total
Dec 19 - Dec 20
Total with taxes and fees
Free Cancellation
13.79 mi from city center
With a stay at Candlewood Suites Annapolis by IHG in Annapolis, you'll be within a 10-minute drive of U.S. Naval Academy and Annapolis Harbour Center.
Pet friendly
Parking included
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

2.5 out of 5
124 Womack Dr Annapolis MD
$86 nightly
The price is $98 total per night
$98 total
Dec 17 - Dec 18
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.9 mi from city center
With a stay at Hampton Inn & Suites Annapolis in Annapolis, you'll be in the business district, within a 10-minute drive of U.S. Naval Academy and Annapolis Harbour Center.
Pool
Breakfast included
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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.

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Chester hotels essential information

Accommodation
1,208 hotels
Lowest Price
$90
Highest Price
$203
Popular hotels
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!, Historic Inns of Annapolis, Graduate by Hilton Annapolis, DoubleTree by Hilton Hotel Annapolis, Hilton Garden Inn Annapolis Downtown, Crowne Plaza Annapolis by IHG, Sonesta ES Suites Annapolis, Country Inn & Suites by Radisson, Annapolis, MD, Annapolis Waterfront Hotel, Autograph Collection, The Westin Annapolis, Candlewood Suites Annapolis by IHG, Hampton Inn & Suites Annapolis

Most Recent Chester Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

5 out of 5
Posted 2 days ago
CheapTickets Verified Review
"Upon entering the entire stay was a 10. The valet, seperate, were very courteous. The front desk staff were friendly and extremely helpful. The hotel was decorated for Christmas and was very festive. The room was clean and very roomy. The location could not have been better, directly across from the State Capital building and a lot of shops and restaurants within walking distance..including the Naval Academy. We are coming back next year for another Christmas in Annapolis."
A verified traveler stayed at Historic Inns of Annapolis
Historic Inns of Annapolis