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Cheap Chester Hotels

Waterfront Sunset Bayview: sleeps 6
Chester MD
3.84 mi from city center
Located in Chester, this vacation home is on the waterfront, within a 15-minute drive of Chesapeake Exploration Center and Island Dog Park.

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.

Historic Inns of Annapolis
58 State Circle Annapolis MD
$159 nightly
The price is $181 total per night
$181 total
May 31 - Jun 1
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.

DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$98 nightly
The price is $111 total per night
$111 total
May 24 - May 25
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.

Sonesta ES Suites Annapolis
170 Admiral Cochrane Dr Edgewater MD
$99 nightly
The price is $113 total per night
$113 total
May 28 - May 29
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 Parole, you'll be in the historical district, within a 10-minute drive of U.S. Naval Academy and Annapolis Harbour Center.

Courtyard by Marriott Annapolis
2559 Riva Rd Annapolis MD
$105 nightly
The price is $120 total per night
$120 total
Jun 7 - Jun 8
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
14.18 mi from city center
When you stay at Courtyard by Marriott Annapolis in Annapolis, you'll be in the business district, within a 15-minute drive of U.S. Naval Academy and Chesapeake Bay.

Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
$110 nightly
The price is $125 total per night
$125 total
May 24 - May 25
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.

The Westin Annapolis
100 Westgate Cir Annapolis MD
$169 nightly
The price is $193 total per night
$193 total
Jun 7 - Jun 8
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.

Country Inn & Suites by Radisson, Annapolis, MD
2600 Housley Road Annapolis MD
$97 nightly
The price is $110 total per night
$110 total
Jun 7 - Jun 8
Total with taxes and fees
Free Cancellation
14.38 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 Westfield Annapolis Mall.

Graduate by Hilton Annapolis
126 West St Annapolis MD
$163 nightly
The price is $186 total per night
$186 total
Jun 7 - Jun 8
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.

Hilton Garden Inn Annapolis Downtown
174 West Street Annapolis MD
$116 nightly
The price is $132 total per night
$132 total
May 24 - May 25
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

Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
$212 nightly
The price is $241 total per night
$241 total
Jun 7 - Jun 8
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
10.53 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 William Paca House and Maryland State House.
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 | $110 |
Highest Price | $241 |
Popular hotels | Waterfront Sunset Bayview: sleeps 6, Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!, Historic Inns of Annapolis, DoubleTree by Hilton Hotel Annapolis, Sonesta ES Suites Annapolis, Courtyard by Marriott Annapolis, Crowne Plaza Annapolis by IHG, The Westin Annapolis, Country Inn & Suites by Radisson, Annapolis, MD, Graduate by Hilton Annapolis, Hilton Garden Inn Annapolis Downtown, Annapolis Waterfront Hotel, Autograph Collection |
Most Recent Chester Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD
3 out of 5
Posted 1 hour ago
CheapTickets Verified Review
"It was clean room. Had a load buzzing humming continuously for the stay, in the wall, like a large transformer running. Elevator was out of service. Ran out of coffee and didn’t refill for extended time. Probably would not choose to stay again."
A verified traveler stayed at Country Inn & Suites by Radisson, Annapolis, MD
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