Compare Cheap Hotels in Chester
Secret Bargains - Save an extra 10% or more on select hotels
Get more for your budget and save up to 50% off select Secret Bargain hotels
Get even more value with CheapTickets Price Guarantee!
Change your flight without a fee on select flights
Cheap Chester Hotels

Historic Inns of Annapolis
58 State Circle Annapolis MD
$130 nightly
The price is $148 total per night
$148 total
Jul 13 - Jul 14
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
Jul 6 - Jul 7
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.77 mi from city center
When you stay at DoubleTree by Hilton Hotel Annapolis in Annapolis, you'll be in the business district, a 5-minute drive from U.S. Naval Academy and 6 minutes from Annapolis City Dock.
Pet friendly
Parking included

Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
$114 nightly
The price is $130 total per night
$130 total
Jul 12 - Jul 13
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

Country Inn & Suites by Radisson, Annapolis, MD
2600 Housley Road Annapolis MD
$111 nightly
The price is $127 total per night
$127 total
Jul 26 - Jul 27
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

Graduate by Hilton Annapolis
126 West St Annapolis MD
$152 nightly
The price is $173 total per night
$173 total
Jul 12 - Jul 13
Total with taxes and fees
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
$106 nightly
The price is $121 total per night
$121 total
Jul 19 - Jul 20
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 Annapolis City Dock and U.S. Naval Academy.
Pet friendly
Free WiFi

St Michaels Inn
1228 S Talbot Street St. Michaels MD
$105 nightly
The price is $116 total per night
$116 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

The Westin Annapolis
100 Westgate Cir Annapolis MD
$169 nightly
The price is $193 total per night
$193 total
Jul 19 - Jul 20
Total with taxes and fees
11.53 mi from city center
When you 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 Annapolis City Dock.
Pool
Spa

Courtyard by Marriott Annapolis
2559 Riva Rd Annapolis MD
$110 nightly
The price is $125 total per night
$125 total
Jul 26 - Jul 27
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

Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
$212 nightly
The price is $241 total per night
$241 total
Jul 12 - Jul 13
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

Best Western Kent Narrows Inn
3101 Main Street Grasonville MD
$125 nightly
The price is $139 total per night
$139 total
Jul 6 - Jul 7
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
2.59 mi from city center
A stay at Best Western Kent Narrows Inn places you in the heart of Grasonville, a 2-minute drive from Chesapeake Exploration Center and 7 minutes from Island Dog Park.

Best Western Annapolis
2520 Riva Rd Annapolis MD
$92 nightly
The price is $105 total per night
$105 total
Jul 26 - Jul 27
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
13.85 mi from city center
When you stay at Best Western Annapolis in Annapolis, you'll be in the business district, within a 10-minute drive of U.S. Naval Academy and Annapolis City Dock.
Breakfast included
Pet friendly
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 | 1,193 hotels |
|---|---|
Lowest Price | $105 |
Highest Price | $241 |
Popular hotels | Historic Inns of Annapolis, DoubleTree by Hilton Hotel Annapolis, Crowne Plaza Annapolis by IHG, Country Inn & Suites by Radisson, Annapolis, MD, Graduate by Hilton Annapolis, Hilton Garden Inn Annapolis Downtown, St Michaels Inn, The Westin Annapolis, Courtyard by Marriott Annapolis, Annapolis Waterfront Hotel, Autograph Collection, Best Western Kent Narrows Inn, Best Western Annapolis |
Most Recent Chester Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD
4 out of 5
Posted less than an hour ago
CheapTickets Verified Review
"The room was nice but the shower didn’t drain properly."
A verified traveler stayed at Country Inn & Suites by Radisson, Annapolis, MD
More to Explore in Chester
Top Picks
- Dundalk Marine Terminal Hotels
- North Beach Hotels
- Business Hotels in Maryland
- Arcade Hotels in St. Michaels
- 3 Star Hotels in Stevensville
- Gambrills Hotels
- 3 Star Hotels in St. Michaels
- Maryland Hotels
- Hotels with a Wedding Venue in Kent Island
- Mcdaniel Hotels
- Beach Resorts & in Kent Island
- Hotels on the River in St. Michaels
- Town Houses in Gibson Island
- Edgewater Hotels
- Green Haven Hotels
- Hotels with Free Airport Shuttle in Maryland
- Hotels near Chesapeake Bay Environmental Center
- Kid Friendly Hotels in Maryland
- Hotels with Balconies in St. Michaels
- Hotels near Easton - Newnam
- 4 Star Hotels in Kent Island
- Hotels with Air Conditioning in Stevensville
- Hawkins Point Hotels
- Oceanfront Hotels in Maryland
- Lake Shore Hotels
- Fishing Resorts & in Kent Island
- 4 Star Hotels in Stevensville
- Casino Resorts & in Maryland
- Arnold Hotels
- Odenton Hotels
- Hotels with Hot Tubs in Maryland
- Hotels with a Lazy River in Maryland
- Hotels with WiFi in Maryland
- Best Western Hotels in Gibson Island
- Inns in Kent Island
- Hotels with Childcare in Maryland
- Hotels with Bars in Maryland
- Fishing Resorts & in Maryland
- Chalets in Maryland
- 5 Star Hotels in Kent Island
- Crofton Hotels
- Hotels near Rocky Point Golf Course
- 4 Star Hotels in Gibson Island
- Oyster Harbor Hotels
- Cheap Hotels in Maryland
- Hotels near Anne Arundel Medical Center
- Extended Stay Hotels in St. Michaels
- Tilghman Hotels
- Town Houses in Maryland
- Harwood Hotels
- Adventure Sport Hotels in Maryland
- 5 Star Hotels in Gibson Island
- Sherwood Hotels
- Edgemere Hotels
- Cheap Hotels in St. Michaels
- Herald Harbor Hotels
- Capsule Hotels in Maryland
- Winery Hotels in St. Michaels
- Sherwood Forest Hotels
- 5 Star Hotels in Stevensville
- Kid Friendly Hotels in St. Michaels
- Hotels with Air Conditioning in Kent Island
- Hotels with Tennis Courts in Stevensville
- Ranches in Maryland
- Gay Friendly Hotels in Maryland
- Annapolis Hotels
- Extended Stay Hotels in Kent Island
- Hotels near U.S. Naval Academy Golf Club
- Farmstay in Gibson Island
- Arden-On-The-Severn Hotels
- Adventure Sport Hotels in Kent Island
- Arcade Hotels in Maryland
- Hotels with WiFi in St. Michaels
- Cape Saint Claire Hotels
- Hotels with Room Service in Kent Island
- Hotels with Free Breakfast in Maryland
- Condo Rentals in Maryland
- Historic Hotels in Kent Island
- St. Michaels Hotels
- Hotels with Air Conditioning in Maryland
- Spa Resorts & in Maryland
- B&B in Gibson Island
- Hotels with Bars in Stevensville
- 5 Star Hotels in Claiborne






