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Cheap Chester hotels

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Chester MD
Located in Chester, this vacation home is on the waterfront, within a 10-minute drive of Chesapeake Exploration Center and Island Dog Park.
Opens in a new windowWaterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is AU$127 per night from 4 Jan to 5 Jan
AU$127
4 Jan - 5 Jan 2026
includes taxes & fees
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 ...
Opens in a new windowDoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.
Opens in a new windowHistoric Inns of Annapolis
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Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
The price is AU$180 per night from 25 Jan to 26 Jan
AU$180
25 Jan - 26 Jan 2026
includes taxes & fees
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 ...
Opens in a new windowCrowne Plaza Annapolis by IHG
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is AU$255 per night from 4 Jan to 5 Jan
AU$255
4 Jan - 5 Jan 2026
includes taxes & fees
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 ...
Opens in a new windowGraduate by Hilton Annapolis
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street Annapolis MD
Fully refundableReserve now, pay when you stay
The price is AU$152 per night from 15 Jan to 16 Jan
AU$152
15 Jan - 16 Jan 2026
includes taxes & fees
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 ...
Opens in a new windowHilton Garden Inn Annapolis Downtown
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road Annapolis MD
Fully refundable
The price is AU$159 per night from 4 Jan to 5 Jan
AU$159
4 Jan - 5 Jan 2026
includes taxes & fees
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 ...
Opens in a new windowCountry Inn & Suites by Radisson, Annapolis, MD
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is AU$374 per night from 4 Jan to 5 Jan
AU$374
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at Annapolis Waterfront Hotel, Autograph Collection, you'll be centrally located in Annapolis, within a 10-minute walk of U.S. Naval Academy and ...
Opens in a new windowAnnapolis Waterfront Hotel, Autograph Collection
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

2.5 out of 5
124 Womack Dr Annapolis MD
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 4 Jan to 5 Jan
AU$138
4 Jan - 5 Jan 2026
includes taxes & fees
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 ...
Opens in a new windowHampton Inn & Suites Annapolis
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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.

Hotels in Chester, Annapolis

Need some time away from spreadsheets, KPIs and your overbearing boss? Located 18 kilometres from the heart of Annapolis, Chester is an excellent place to base yourself while discovering Maryland's thrilling capital.

If sightseeing is on the agenda, it’s time to get a move on. Annapolis has stacks of well-known attractions to check out, including Six Flags America, the U.S. Naval Academy and William Paca House.

Visitors after some free suggestions and brochures ought to make Chesapeake Exploration Center a priority. Like to base yourself someplace nearby? Check the rates at the Hilton Garden Inn Kent Island and Best Western Kent Narrows Inn.

Why not get your mates together and plan the first evening of your getaway over a hot coffee at Starbucks? It's not far away, and there's plenty of delicious cakes to keep you going. When your tum really starts grumbling, mosey on over to TIPS BBQ and suss out their impressive menu. If all that grub has left you a tad thirsty, Frix's Fire Grill is just a stone's throw away. It's a great place to pull up a stool and chat with the locals!

Accommodation options near Chester

Totes over trying to find a place to kick your feet up in Chester? Then how about heading out a bit further to Annapolis? It's about 18 kilometres away from Chester. The Annapolis Waterfront Hotel, Autograph Collection and Loews Annapolis Hotel are two cool options worth sussing out.

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Chester hotels essential information

Accommodation
1,193 hotels
Lowest Price
AU$127
Highest Price
AU$374
Popular hotels
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!, DoubleTree by Hilton Hotel Annapolis, Historic Inns of 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, Hampton Inn & Suites Annapolis

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