Chester accommodation from AU$101

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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
3.06 km from city centre
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!: Family-friendly holiday home with free WiFi and parking. Located on the waterfront.
Kitchen
Washing machine
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
17.34 km from city centre
Historic Inns of Annapolis: Pet-friendly hotel with free WiFi and a bar/lounge. Located in the business district.
Pet-friendly
Free WiFi
Free cancellation
Reserve now, pay when you stay
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
The price is AU$213 per night
AU$213
21 Dec - 22 Dec
includes taxes & fees
18.04 km from city centre
Graduate by Hilton Annapolis: Pet-friendly hotel with free WiFi and a bar/lounge. Located in the city centre.
Pet-friendly
Free WiFi
Free cancellation
Reserve now, pay when you stay
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
The price is AU$101 per night
AU$101
4 Jan - 5 Jan 2026
includes taxes & fees
22.18 km from city centre
DoubleTree by Hilton Hotel Annapolis: Pet-friendly hotel with free WiFi and free parking. Located in a shopping district.
Pet-friendly
Parking included
Free cancellation
Reserve now, pay when you stay
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street Annapolis MD
The price is AU$137 per night
AU$137
28 Dec - 29 Dec
includes taxes & fees
18.24 km from city centre
Hilton Garden Inn Annapolis Downtown: Pet-friendly hotel with free WiFi and a bar/lounge. Located in the city centre.
Pet-friendly
Free WiFi
Free cancellation
Reserve now, pay when you stay
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
The price is AU$173 per night
AU$173
9 Dec - 10 Dec
includes taxes & fees
22.02 km from city centre
Crowne Plaza Annapolis by IHG: Business-friendly hotel with free WiFi and free parking. Guests love the helpful staff!
Pool
Parking included
Free cancellation
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
The price is AU$143 per night
AU$143
28 Dec - 29 Dec
includes taxes & fees
22.62 km from city centre
Sonesta ES Suites Annapolis: Pet-friendly hotel with free breakfast and free WiFi. Located in the historical district.
Pool
Breakfast included
Free cancellation
Reserve now, pay when you stay
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 AU$144 per night
AU$144
28 Dec - 29 Dec
includes taxes & fees
23.1 km from city centre
Country Inn & Suites by Radisson, Annapolis, MD: Pet-friendly hotel with free breakfast and free WiFi. Located in a shopping district.
Pool
Hot tub
Free cancellation
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
The price is AU$307 per night
AU$307
14 Dec - 15 Dec
includes taxes & fees
17.01 km from city centre
Annapolis Waterfront Hotel, Autograph Collection: Pet-friendly hotel with free WiFi and a bar/lounge. Located in the historical district.
Pet-friendly
Free WiFi
Free cancellation
Reserve now, pay when you stay
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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.

Accommodation In Chester

Located 30 kilometres east of central Maryland, Chester is a great neighbourhood to visit when travelling through the area.

If you are visiting Maryland, you should know about National Aquarium in Baltimore. It draws visitors from all around the globe.

The recommendations at Chesapeake Exploration Center will help you get around the area. Check the rates at the Hilton Garden Inn Kent Island and Best Western Kent Narrows Inn if you want to rest your head close by.

Can't face the day without at least one coffee? You'll be relieved to know Chester has some excellent cafes. Capriotti's Sandwich Shop is a local favourite, offering a range of hot drinks and snacks. Unfortunately, we can't keep going on caffeine alone. Have a flick through the menu at Cracker Barrel Old Country Store when your stomach starts to rumble. And of course, you haven't truly experienced Chester until you've said hello to the locals at the neighbourhood bar. Here, Cafe Sado is the place to be.

Accommodation options near Chester

The Historic Kent Manor Inn and The Inn at Chesapeake Bay Beach Club are a couple of worthwhile places to rest your head if you can't find the perfect accommodations in Chester.

Chester features some fabulous accommodations. So, if you're ready to explore the delights of Maryland, Wotif can take you there, on time, on budget and in style!

Chester hotels essential information

Accommodation
1,208 hotels
Lowest Price
AU$101
Highest Price
AU$307
Popular hotels
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!, Historic Inns of Annapolis, Graduate by Hilton Annapolis, DoubleTree by Hilton Hotel Annapolis, Hilton Garden Inn Annapolis Downtown, Crowne Plaza Annapolis by IHG, Sonesta ES Suites Annapolis, Country Inn & Suites by Radisson, Annapolis, MD, Annapolis Waterfront Hotel, Autograph Collection

New reviews! Best hotels in Chester

Graduate by Hilton Annapolis
Wotif Verified Review
5 / 5
Very nice hotel. The dog park could have better lighting.
A verified traveller stayed at Graduate by Hilton Annapolis
Posted 20 hours ago
Graduate by Hilton Annapolis

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