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Check prices in Chester for tonight, Jul 20 - Jul 21
Jul 20 - Jul 21
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Check prices in Chester for tomorrow night, Jul 21 - Jul 22
Jul 21 - Jul 22
Next weekend
Check prices in Chester for next weekend, Jul 25 - Jul 27
Jul 25 - Jul 27

Most frequently booked Chester hotels

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
17.34 km from city centre
Get rates
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions The Colonial Players and 97, 99 and 101 East Street are located nearby.
Pet-friendly
Free WiFi
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
18.04 km from city centre
The price is CA $213 per night
CA $213
CA $243 total
Aug 3 - Aug 4
includes taxes & fees
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Annapolis City Dock and Annapolis Civil Rights Plaque are located nearby.
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court, Annapolis, MD
Free cancellation
Reserve now, pay when you stay
22.18 km from city centre
The price is CA $140 per night
CA $140
CA $160 total
Aug 17 - Aug 18
includes taxes & fees
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Annapolis Harbor Center Shopping Center and Westfield Annapolis Mall are located nearby.
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
Free cancellation
23.1 km from city centre
The price is CA $133 per night
CA $133
CA $152 total
Jul 27 - Jul 28
includes taxes & fees
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Annapolis Bowl and Westfield Annapolis Mall are located nearby.
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St, Annapolis, MD
Free cancellation
Reserve now, pay when you stay
17.01 km from city centre
The price is CA $302 per night
CA $302
CA $344 total
Jul 27 - Jul 28
includes taxes & fees
Stay at this 4-star eco-certified hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Annapolis City Dock and Ego Alley are located nearby.
Pet-friendly
Free WiFi
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street, Annapolis, MD
Free cancellation
Reserve now, pay when you stay
18.24 km from city centre
The price is CA $139 per night
CA $139
CA $158 total
Aug 17 - Aug 18
includes taxes & fees
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Annapolis City Dock and Annapolis Civil Rights Plaque are located nearby.
Best Western Annapolis

Best Western Annapolis

2.5 out of 5
2520 Riva Rd, Annapolis, MD
Free cancellation
Reserve now, pay when you stay
22.31 km from city centre
The price is CA $112 per night
CA $112
CA $128 total
Jul 22 - Jul 23
includes taxes & fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Annapolis City Dock and Annapolis Harbor Center Shopping Center are located nearby.
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

3 out of 5
189 Admiral Cochrane Drive, Annapolis, MD
Free cancellation
Reserve now, pay when you stay
22.47 km from city centre
The price is CA $134 per night
CA $134
CA $153 total
Jul 27 - Jul 28
includes taxes & fees
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Annapolis Harbor Center Shopping Center and Annapolis Harbour Center are located nearby.
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

3 out of 5
2559 Riva Rd, Annapolis, MD
Free cancellation
Reserve now, pay when you stay
22.83 km from city centre
The price is CA $137 per night
CA $137
CA $156 total
Aug 4 - Aug 5
includes taxes & fees
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Annapolis Harbor Center Shopping Center and Annapolis Harbour Center are located nearby.
Don't see what you're looking for?
See all available properties in Chester
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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.

Top hotels in Chester for Extended Stay

Town View King Apartment with Private Beach - Walk to shops and restaurants

Town View King Apartment with Private Beach - Walk to shops and restaurants

Oxford
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
1,239 hotels
Lowest Price
CA $112
Highest Price
CA $302
Popular hotels
Historic Inns of Annapolis, Graduate by Hilton Annapolis, DoubleTree by Hilton Hotel Annapolis, Country Inn & Suites by Radisson, Annapolis, MD, Annapolis Waterfront Hotel, Autograph Collection, Hilton Garden Inn Annapolis Downtown, Best Western Annapolis, SpringHill Suites by Marriott Annapolis, Courtyard by Marriott Annapolis

Frequently asked questions

What are the top kid-friendly hotels in Chester?
Family vacations are where treasured memories are made, but it's no secret that traveling with children can be daunting. These kid-friendly Chester hotels come with perks that aim to keep adventurers of all ages comfortable and happy: The whole gang will love staying at New! Stylish downtown home w/awesome outdoor area!. A nearby beach and free WiFi are just a couple of the things that help make this place a winner. Also look into Bentons Pleasure- Cox Creek, Pier and Sunsets!. It comes with a playground, a king bed and lots of opportunities to spend time together.
Where can I find cheap hotels in Chester?
At Travelocity you'll find really nice hotels in Chester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Chester rather than in Chester. We may find you even better rates, too.
How do I find the best Chester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Chester then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Chester?
The cheapest hotel in Chester is CA $112 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Chester?
There are 1,239 hotels in Chester on Travelocity.
What are the best hotels in Chester?
Chester has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Chester for you!
When is the best time to visit Chester?
If you want the joy of a fun-filled trip in peak season, visit Chester during May, June and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Chester?
Based on historic data is usually the cheapest month to visit Chester. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Chester?
There are multiple hotels in Chester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Chester. We have plenty of kid-friendly hotels in Chester to choose from on Travelocity!
Why book a hotel in Chester through Travelocity?
Because we have the top hotels in Chester! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Chester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Chester hotel reviews by fellow wanderers

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

5 out of 5
Posted 15 hours ago
Travelocity Verified Review
"Clean and comfortable room. Located conveniently. The fireplace and tub were nice."
A verified traveller stayed at Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD

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