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Cheap Chester Hotels

Historic Inns of Annapolis
58 State Circle Annapolis MD
$130 nightly
The price is $148 total per night
$148 total
Jul 5 - Jul 6
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

DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$111 nightly
The price is $127 total per night
$127 total
Jun 16 - Jun 17
Total with taxes and fees
13.77 mi from city center
When you stay at DoubleTree by Hilton Hotel Annapolis in Annapolis, you'll be in the business district, within a 15-minute drive of U.S. Naval Academy and Sandy Point State Park.
Pet friendly
Parking included

Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
$110 nightly
The price is $125 total per night
$125 total
Jul 5 - Jul 6
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

Graduate by Hilton Annapolis
126 West St Annapolis MD
$163 nightly
The price is $186 total per night
$186 total
Jul 12 - Jul 13
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 Annapolis City Dock and U.S. Naval Academy.
Pet friendly
Free WiFi

Hilton Garden Inn Annapolis Downtown
174 West Street Annapolis MD
$139 nightly
The price is $158 total per night
$158 total
Jul 1 - Jul 2
Total with taxes and fees
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 Annapolis City Dock and U.S. Naval Academy.
Pet friendly
Free WiFi

Country Inn & Suites by Radisson, Annapolis, MD
2600 Housley Road Annapolis MD
$104 nightly
The price is $118 total per night
$118 total
Jun 21 - Jun 22
Total with taxes and fees
Free Cancellation
14.38 mi from city center
When you 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 City Dock.
Pool
Hot Tub

Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
$246 nightly
The price is $280 total per night
$280 total
Jul 1 - Jul 2
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.
Pet friendly
Free WiFi

Courtyard by Marriott Annapolis
2559 Riva Rd Annapolis MD
$98 nightly
The price is $112 total per night
$112 total
Jul 5 - Jul 6
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 10-minute drive of U.S. Naval Academy and Annapolis City Dock.
Pool
Hot Tub

The Westin Annapolis
100 Westgate Cir Annapolis MD
$169 nightly
The price is $193 total per night
$193 total
Jul 5 - Jul 6
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
11.53 mi from city center
When you stay at The Westin Annapolis in Annapolis, you'll be in the historical district, within a 15-minute drive of U.S. Naval Academy and Sandy Point State Park.
Pool
Spa

St Michaels Inn
1228 S Talbot Street St. Michaels MD
$124 nightly
The price is $136 total per night
$136 total
Jul 6 - Jul 7
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
14.92 mi from city center
When you stay at St Michaels Inn in St. Michaels, you'll be in the historical district, within a 5-minute drive of St. Michaels Winery and Chesapeake Bay Maritime Museum.
Pool
Breakfast included

Hampton Inn & Suites Annapolis
124 Womack Dr Annapolis MD
$116 nightly
The price is $132 total per night
$132 total
Jul 6 - Jul 7
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.9 mi from city center
When you 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 City Dock.
Pool
Breakfast included

Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
$621 nightly
The price is $683 total per night
$683 total
Jun 21 - Jun 22
Total with taxes and fees
13.29 mi from city center
A stay at Inn at Perry Cabin places you in the heart of St. Michaels, within a 15-minute walk of Perry Cabin Park and Saint Michaels Town Hall.
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.
Chester hotels essential information
Accommodation | 1,191 hotels |
|---|---|
Lowest Price | $112 |
Highest Price | $683 |
Popular hotels | Historic Inns of Annapolis, DoubleTree by Hilton Hotel Annapolis, Crowne Plaza Annapolis by IHG, Graduate by Hilton Annapolis, Hilton Garden Inn Annapolis Downtown, Country Inn & Suites by Radisson, Annapolis, MD, Annapolis Waterfront Hotel, Autograph Collection, Courtyard by Marriott Annapolis, The Westin Annapolis, St Michaels Inn, Hampton Inn & Suites Annapolis, Inn at Perry Cabin |
Most Recent Chester Hotel Reviews

Crowne Plaza Annapolis by IHG
5 out of 5
Posted 1 hour ago
CheapTickets Verified Review
"Quality hotel, good value"
A verified traveler stayed at Crowne Plaza Annapolis by IHG
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