Book Chester hotels

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Check hotel availability in Chester

Cheap Chester hotels

Waterfront Sunset Bayview: sleeps 6

Waterfront Sunset Bayview: sleeps 6

Chester MD
Stay at this holiday home in Chester. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Bodkin Island and Chesapeake Bay Environmental Center ...
Opens in a new windowWaterfront Sunset Bayview: sleeps 6
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$218 per night from 31 May to 1 June
NZ$218
31 May - 1 June
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
Save an average of 15% on thousands of hotels when you're signed in
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
The price is NZ$293 per night from 25 May to 26 May
NZ$293
25 May - 26 May
includes taxes & fees
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
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
The price is NZ$199 per night from 27 May to 28 May
NZ$199
27 May - 28 May
includes taxes & fees
Stay at this business-friendly hotel in Parole. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowSonesta ES Suites Annapolis
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

3 out of 5
2559 Riva Rd Annapolis MD
Fully refundableReserve now, pay when you stay
The price is NZ$201 per night from 31 May to 1 June
NZ$201
31 May - 1 June
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the helpful staff and the ...
Opens in a new windowCourtyard by Marriott Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
The price is NZ$210 per night from 24 May to 25 May
NZ$210
24 May - 25 May
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
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir Annapolis MD
The price is NZ$323 per night from 7 June to 8 June
NZ$323
7 June - 8 June
includes taxes & fees
Stay at this spa hotel in Annapolis. Enjoy free Wi-Fi, a full-service spa and breakfast (surcharge). Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowThe Westin Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road Annapolis MD
The price is NZ$201 per night from 31 May to 1 June
NZ$201
31 May - 1 June
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
Don't see what you're looking for?
See all available properties in Chester
View all properties
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
1,203 hotels
Lowest Price
NZ$199
Highest Price
NZ$323
Popular hotels
Waterfront Sunset Bayview: sleeps 6, Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!, DoubleTree by Hilton Hotel Annapolis, Historic Inns of Annapolis, Sonesta ES Suites Annapolis, Courtyard by Marriott Annapolis, Crowne Plaza Annapolis by IHG, The Westin Annapolis, Country Inn & Suites by Radisson, Annapolis, MD

Most recent Chester hotel reviews

Top Picks

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.