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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
Stay at this family-friendly holiday home in Chester. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Northern Chesapeake Bay and Matapeake ...
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 NZ$148 per night from 4 Jan to 5 Jan
NZ$148
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
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
Stay at this historic hotel in Annapolis. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
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 NZ$208 per night from 3 Jan to 4 Jan
NZ$208
3 Jan - 4 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
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 NZ$268 per night from 29 Dec to 30 Dec
NZ$268
29 Dec - 30 Dec
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the bar and the helpful ...
Opens in a new windowGraduate by Hilton Annapolis
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 NZ$385 per night from 29 Dec to 30 Dec
NZ$385
29 Dec - 30 Dec
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, a rooftop terrace and breakfast (surcharge). Our guests praise the helpful staff and the ...
Opens in a new windowAnnapolis Waterfront Hotel, Autograph Collection
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 NZ$177 per night from 5 Jan to 6 Jan
NZ$177
5 Jan - 6 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the helpful staff ...
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 NZ$196 per night from 11 Jan to 12 Jan
NZ$196
11 Jan - 12 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
Opens in a new windowCountry Inn & Suites by Radisson, Annapolis, MD
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 NZ$177 per night from 28 Dec to 29 Dec
NZ$177
28 Dec - 29 Dec
includes taxes & fees
Stay at this family-friendly hotel in Annapolis. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the breakfast and the helpful staff ...
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

Are you planning to spend time in Annapolis? Hoping to find somewhere to stay in or near Chester? We will sort you out.

Accommodations that are fairly close to the CBD of Chester include the Historic Kent Manor Inn and Hilton Garden Inn Kent Island.

The Inn at Perry Cabin by Belmond is 20 kilometres from the heart of Chester. Another hotel is the Annapolis Waterfront Hotel, Autograph Collection, which is situated 18 kilometres away. The Five Gables Inn and Spa and the Loews Annapolis Hotel are two other options in Chester.

Looking to venture a bit further afield? You've picked the right place! Central Maryland has many other attractions to keep you busy throughout your stay. Photographers will love Central Maryland's coastal plains. If the great outdoors are not your bag, explore a few of the region's street art. Or join the locals in the shore fishing while you're here.

The nearest places to stay in Annapolis are Bowie and Arnold. Bowie is 40 kilometres to the west of Chester, while Arnold is 20 kilometres to the northwest of Chester. Hotels in Bowie include the TownePlace Suites Bowie Town Center and Comfort Inn Conference Center. Arnold apartments and hotels are the Comfort Inn Annapolis and Village Inn.

Just because you're travelling in Annapolis, doesn't mean you can't enjoy your love of all things sport. Comcast Center is 55 kilometres to the west of Chester. The College Park Marriott Hotel & Conference Center and the Hampton Inn College Park are near all the action.

Baltimore Washington International Thurgood Marshall Airport is the most commonly used gateway to Chester. Nearby hotels include the Residence Inn by Marriott Baltimore BWI Airport and the BWI Airport Marriott.

Chester hotels essential information

Accommodation
1,192 hotels
Lowest Price
NZ$148
Highest Price
NZ$385
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, Annapolis Waterfront Hotel, Autograph Collection, Hilton Garden Inn Annapolis Downtown, Country Inn & Suites by Radisson, Annapolis, MD, Hampton Inn & Suites Annapolis

Most recent Chester hotel reviews

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