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Cheap Chester Hotels

DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$75 nightly
The price is $85 total per night
$85 total
Feb 8 - Feb 9
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

Graduate by Hilton Annapolis
126 West St Annapolis MD
$147 nightly
The price is $167 total per night
$167 total
Jan 25 - Jan 26
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

Historic Inns of Annapolis
58 State Circle Annapolis MD
$169 nightly
The price is $193 total per night
$193 total
Feb 5 - Feb 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

Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
$186 nightly
The price is $212 total per night
$212 total
Jan 25 - Jan 26
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

Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
$106 nightly
The price is $121 total per night
$121 total
Feb 15 - Feb 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

Hilton Garden Inn Annapolis Downtown
174 West Street Annapolis MD
$89 nightly
The price is $102 total per night
$102 total
Feb 9 - Feb 10
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

Country Inn & Suites by Radisson, Annapolis, MD
2600 Housley Road Annapolis MD
$91 nightly
The price is $104 total per night
$104 total
Feb 8 - Feb 9
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 Annapolis Mall Shopping Center.
Pool
Hot Tub

The Westin Annapolis
100 Westgate Cir Annapolis MD
$149 nightly
The price is $170 total per night
$170 total
Jan 18 - Jan 19
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

Hyatt Place Kent Narrows & Marina
3028 KENT NARROW WAY S Grasonville MD
$135 nightly
The price is $150 total per night
$150 total
Jan 24 - Jan 25
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
2.47 mi from city center
Located in Grasonville, Hyatt Place Kent Narrows & Marina is in the historical district, a 2-minute drive from Chesapeake Exploration Center and 7 minutes from Island Dog Park.
Pool
Pet friendly

Sonesta ES Suites Annapolis
170 Admiral Cochrane Dr Edgewater MD
$91 nightly
The price is $104 total per night
$104 total
Feb 4 - Feb 5
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

Hampton Inn & Suites Annapolis
124 Womack Dr Annapolis MD
$89 nightly
The price is $102 total per night
$102 total
Jan 25 - Jan 26
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

St Michaels Inn
1228 S Talbot Street St. Michaels MD
$101 nightly
The price is $111 total per night
$111 total
Jan 18 - Jan 19
Total with taxes and fees
Free Cancellation
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
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 | 1,193 hotels |
|---|---|
Lowest Price | $85 |
Highest Price | $212 |
Popular hotels | DoubleTree by Hilton Hotel Annapolis, Graduate by Hilton Annapolis, Historic Inns of Annapolis, Annapolis Waterfront Hotel, Autograph Collection, Crowne Plaza Annapolis by IHG, Hilton Garden Inn Annapolis Downtown, Country Inn & Suites by Radisson, Annapolis, MD, The Westin Annapolis, Hyatt Place Kent Narrows & Marina, Sonesta ES Suites Annapolis, Hampton Inn & Suites Annapolis, St Michaels Inn |
Most Recent Chester Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD
5 out of 5
Posted 3 days ago
CheapTickets Verified Review
"Wonderful staff, great options for breakfast, room is perfect and quiet and clean. The amenities work nicely, gym is great and Thai is where I would stay again in the future. "
A verified traveler stayed at Country Inn & Suites by Radisson, Annapolis, MD
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