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Most frequently booked Chester hotels

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Free cancellation
Reserve now, pay when you stay
17.34 km from city centre
The price is CA $128 per night
CA $128
CA $194 total
Jul 15 - Jul 16
includes taxes & fees
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
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 $135 per night
CA $135
CA $154 total
Jul 5 - Jul 6
includes taxes & fees
Book a stay at this 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.
Pet-friendly
Parking included
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
22.02 km from city centre
The price is CA $156 per night
CA $156
CA $178 total
Jul 5 - Jul 6
includes taxes & fees
Book a stay at this 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 Westfield Annapolis Mall and Annapolis Mall Shopping Center are located nearby.
Pool
Parking included
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
23.15 km from city centre
The price is CA $147 per night
CA $147
CA $167 total
Jul 26 - Jul 27
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 Bowl and Westfield Annapolis Mall are located nearby.
Pool
Hot tub
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Free cancellation
Reserve now, pay when you stay
18.04 km from city centre
The price is CA $232 per night
CA $232
CA $264 total
Jul 12 - Jul 13
includes taxes & fees
Book a stay at this 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 Civil Rights Plaque and ARTFX Gallery of Fine Crafts and Arts are located nearby.
Pet-friendly
Free WiFi
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Free cancellation
Reserve now, pay when you stay
24.03 km from city centre
The price is CA $131 per night
CA $131
CA $144 total
Jul 7 - Jul 8
includes taxes & fees
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saint Michaels Village and Classic Motor Museum are located nearby.
Pool
Breakfast included
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 $164 per night
CA $164
CA $187 total
Jul 19 - Jul 20
includes taxes & fees
Book a stay at this 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 Civil Rights Plaque and ARTFX Gallery of Fine Crafts and Arts are located nearby.
Pet-friendly
Free WiFi
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir Annapolis MD
Free cancellation
Reserve now, pay when you stay
18.57 km from city centre
The price is CA $240 per night
CA $240
CA $274 total
Jul 5 - Jul 6
includes taxes & fees
Book a stay at this spa hotel in Annapolis. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Sandy Point State Park and Maryland Hall for Creative Arts are located nearby.
Pool
Spa
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 $151 per night
CA $151
CA $172 total
Jul 7 - Jul 8
includes taxes & fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a fitness center. 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.
Pool
Hot tub
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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.

Chester hotels essential information

Accommodation
1,190 hotels
Lowest Price
CA $144
Highest Price
CA $274
Popular hotels
Historic Inns of Annapolis, DoubleTree by Hilton Hotel Annapolis, Crowne Plaza Annapolis by IHG, Country Inn & Suites by Radisson, Annapolis, MD, Graduate by Hilton Annapolis, St Michaels Inn, Hilton Garden Inn Annapolis Downtown, The Westin 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 $144 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 1,190 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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

5 out of 5
Posted 8 hours ago
Travelocity Verified Review
"Great spot to stay! Had the pleasure of checking in with Trendy- an amazingly refreshing soul that is passionate both about his job and customer satisfaction. I felt very welcomed and informed upon arrival- and he was key in making that happen. The property is worth more than what you pay. Spacious rooms, comfy beds, warm water, and close to a mall, bowling alley, and more shopping centers. It offers an on property bar/restaurant, large/deep life-guarded pool, a well stocked gift shop with alcoholic beverages, toiletries, food and snacks. My girlfriend and I thoroughly enjoyed our stay there more than what we did when we stayed in D.C. at AC by Marriot the nights before. Free parking too! Strongly recommend if you’re on a budget but still want an enjoyable stay."
A verified traveller stayed at DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis