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Cheap Chester Hotels

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
58 State Circle Annapolis MD
$208 nightly
The price is $237 total per night
$237 total
Mar 1 - Mar 2
Total with taxes and fees
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
$84 nightly
The price is $95 total per night
$95 total
Mar 8 - Mar 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
$162 nightly
The price is $185 total per night
$185 total
Mar 22 - Mar 23
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 Asbury United Methodist Church.
Pet friendly
Free WiFi

Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
$103 nightly
The price is $118 total per night
$118 total
Feb 24 - Feb 25
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
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.

Hilton Garden Inn Annapolis Downtown
174 West Street Annapolis MD
$93 nightly
The price is $106 total per night
$106 total
Mar 2 - Mar 3
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 Asbury United Methodist Church.
Pet friendly
Free WiFi

Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
$178 nightly
The price is $203 total per night
$203 total
Mar 22 - Mar 23
Total with taxes and fees
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

Country Inn & Suites by Radisson, Annapolis, MD
2600 Housley Road Annapolis MD
$95 nightly
The price is $109 total per night
$109 total
Mar 15 - Mar 16
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.

Sonesta ES Suites Annapolis
170 Admiral Cochrane Dr Edgewater MD
$91 nightly
The price is $104 total per night
$104 total
Mar 15 - Mar 16
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.
Pool
Breakfast included

The Westin Annapolis
100 Westgate Cir Annapolis MD
$179 nightly
The price is $204 total per night
$204 total
Mar 1 - Mar 2
Total with taxes and fees
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.

Courtyard by Marriott Annapolis
2559 Riva Rd Annapolis MD
$100 nightly
The price is $114 total per night
$114 total
Mar 15 - Mar 16
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
14.18 mi from city center
With a 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 Harbour Center.
Pool
Hot Tub

Hyatt Place Kent Narrows & Marina
3028 KENT NARROW WAY S Grasonville MD
$116 nightly
The price is $129 total per night
$129 total
Mar 2 - Mar 3
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
2.47 mi from city center
Located in Kent Narrows, 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.
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 | 1,177 hotels |
|---|---|
Lowest Price | $95 |
Highest Price | $237 |
Popular hotels | Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!, Historic Inns of Annapolis, DoubleTree by Hilton Hotel Annapolis, Graduate by Hilton Annapolis, Crowne Plaza Annapolis by IHG, Hilton Garden Inn Annapolis Downtown, Annapolis Waterfront Hotel, Autograph Collection, Country Inn & Suites by Radisson, Annapolis, MD, Sonesta ES Suites Annapolis, The Westin Annapolis, Courtyard by Marriott Annapolis, Hyatt Place Kent Narrows & Marina |
Most Recent Chester Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD
5 out of 5
Posted 16 hours ago
CheapTickets Verified Review
"Nice large room, clean, and temperature controls worked as expected. Front deck personnel were pleasant. Breakfast was good, with a variety of options."
A verified traveler stayed at Country Inn & Suites by Radisson, Annapolis, MD
- Sonesta ES Suites Annapolis
- The Westin Annapolis
- Courtyard by Marriott Annapolis
- Hyatt Place Kent Narrows & Marina
- SpringHill Suites by Marriott Annapolis
- Candlewood Suites Annapolis by IHG
- St Michaels Inn
- Hampton Inn & Suites Annapolis
- Best Western Kent Narrows Inn
- Fairfield Inn & Suites By Marriott Annapolis
- The Inn at Chesapeake Bay Beach Club
- Hilton Garden Inn Annapolis
- The Wildset
- Best Western Annapolis
- Hilton Garden Inn Kent Island Marina
- Best Western Plus Easton Inn & Suites
- Inn at Perry Cabin
- Holiday Inn Express Annapolis East-Kent Island by IHG
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