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Tonight
Check prices in Chester for tonight, Mar. 26 - Mar. 27
Mar. 26 - Mar. 27
Tomorrow night
Check prices in Chester for tomorrow night, Mar. 27 - Mar. 28
Mar. 27 - Mar. 28
This weekend
Check prices in Chester for this weekend, Mar. 28 - Mar. 30
Mar. 28 - Mar. 30
Next weekend
Check prices in Chester for next weekend, Apr. 4 - Apr. 6
Apr. 4 - Apr. 6

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 $184 per night
CA $184
CA $257 total
includes taxes & fees
31 Mar - 1 Apr
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
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 $126 per night
CA $126
CA $144 total
includes taxes & fees
2 Apr - 3 Apr
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.
Pool
Hot tub
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 $157 per night
CA $157
CA $179 total
includes taxes & fees
2 Apr - 3 Apr
Stay at this 3.5-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 Westfield Annapolis Mall and Annapolis Mall Shopping Center are located nearby.
Parking included
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 $213 per night
CA $213
CA $242 total
includes taxes & fees
22 Apr - 23 Apr
Stay at this 4-star spa hotel in Annapolis. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Maryland Hall for Creative Arts and Ballet Theater of Maryland are located nearby.
Pool
Spa
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 $120 per night
CA $120
CA $137 total
includes taxes & fees
13 Apr - 14 Apr
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 Civil Rights Plaque and Asbury United Methodist Church are located nearby.
Pet-friendly
Free WiFi
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
3028 KENT NARROW WAY S, Grasonville, MD
Free cancellation
Reserve now, pay when you stay
3.99 km from city centre
The price is CA $175 per night
CA $175
CA $194 total
includes taxes & fees
13 Apr - 14 Apr
Stay at this 3-star business-friendly hotel in Grasonville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chesapeake Bay Environmental Center and Paul Reed Smith Guitars are located nearby.
Pool
Pet-friendly
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 $133 per night
CA $133
CA $151 total
includes taxes & fees
31 Mar - 1 Apr
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.
Parking included
Free WiFi
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 $132 per night
CA $132
CA $151 total
includes taxes & fees
6 Apr - 7 Apr
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.
Pool
Hot tub
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St, Annapolis, MD
17.01 km from city centre
The price is CA $274 per night
CA $274
CA $312 total
includes taxes & fees
20 Apr - 21 Apr
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 Ego Alley and Susan Campbell Park are located nearby.
Pet-friendly
Free WiFi
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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
10/10 Exceptional! (3 reviews)
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
1,204 hotels
Lowest Price
CA $120
Highest Price
CA $274
Popular hotels
Historic Inns of Annapolis, Country Inn & Suites by Radisson, Annapolis, MD, Crowne Plaza Annapolis by IHG, The Westin Annapolis, Hilton Garden Inn Annapolis Downtown, Hyatt Place Kent Narrows & Marina, Courtyard by Marriott Annapolis, SpringHill Suites by Marriott Annapolis, Annapolis Waterfront Hotel, Autograph Collection

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 $120 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 1,204 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

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

5 out of 5
Posted 1 day ago
Travelocity Verified Review
"Very large comfortable rooms. Plenty of room in the kitchen and bathrooms too. Beds and pillows were comfortable. Friendly front desk support. Ample hot and cold breakfast with plenty of seating. Surprised by a $7 per day parking fee."
A verified traveller stayed at Sonesta ES Suites Annapolis
Sonesta ES Suites Annapolis

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