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Tonight
Check prices in Chester for tonight, May 15 - May 16
May 15 - May 16
Tomorrow night
Check prices in Chester for tomorrow night, May 16 - May 17
May 16 - May 17
This weekend
Check prices in Chester for this weekend, May 15 - May 17
May 15 - May 17

Most frequently booked Chester hotels

Waterfront Sunset Bayview: sleeps 6

Waterfront Sunset Bayview: sleeps 6

Chester MD
6.18 km from city centre
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Stay at this vacation home in Chester. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Bodkin Island and Chesapeake Bay Environmental Center are located nearby.
Kitchen
Washer
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
Get rates
Book a stay at this family-friendly vacation home in Chester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Northern Chesapeake Bay and Matapeake State Park are located nearby.
Kitchen
Washer
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 $160 per night
CA $160
CA $229 total
May 25 - May 26
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 Chesapeake Bay Bridge and The Colonial Players 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 $156 per night
CA $156
CA $178 total
May 26 - May 27
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 Annapolis Mall Shopping Center are located nearby.
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr Edgewater MD
Free cancellation
Reserve now, pay when you stay
22.62 km from city centre
The price is CA $140 per night
CA $140
CA $160 total
May 27 - May 28
includes taxes & fees
Book a stay at this business-friendly hotel in Parole. Enjoy free breakfast, free WiFi, and an outdoor pool. 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.
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 $144 per night
CA $144
CA $164 total
May 31 - Jun 1
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.
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Free cancellation
22.02 km from city centre
The price is CA $151 per night
CA $151
CA $172 total
May 24 - May 25
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 Annapolis Mall Shopping Center and Westfield Annapolis Mall are located nearby.
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 $232 per night
CA $232
CA $264 total
Jun 7 - Jun 8
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 Chesapeake Bay Bridge and Maryland Hall for Creative Arts 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
23.15 km from city centre
The price is CA $142 per night
CA $142
CA $161 total
Jun 7 - Jun 8
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 Annapolis Mall Shopping Center are located nearby.
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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
1,206 hotels
Lowest Price
CA $160
Highest Price
CA $264
Popular hotels
Waterfront Sunset Bayview: sleeps 6, Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!, Historic Inns of Annapolis, DoubleTree by Hilton Hotel Annapolis, Sonesta ES Suites Annapolis, Courtyard by Marriott Annapolis, Crowne Plaza Annapolis by IHG, The Westin Annapolis, Country Inn & Suites by Radisson, Annapolis, MD

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 $160 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 1,206 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

Historic Inns of Annapolis

Historic Inns of Annapolis

5 out of 5
Posted 1 hour ago
Travelocity Verified Review
"Marylan house was great. Perfect location and clean- room was cute and perfect. I was there on business but want to come back to the same place. awesome - awesome - awesome,"
A verified traveller stayed at Historic Inns of Annapolis
Historic Inns of Annapolis