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Tonight
Check prices in Chester for tonight, Aug 25 - Aug 26
Aug 25 - Aug 26
Tomorrow night
Check prices in Chester for tomorrow night, Aug 26 - Aug 27
Aug 26 - Aug 27
This weekend
Check prices in Chester for this weekend, Aug 28 - Aug 30
Aug 28 - Aug 30
Next weekend
Check prices in Chester for next weekend, Sep 4 - Sep 6
Sep 4 - Sep 6

Most frequently booked Chester hotels

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
22.18 km from city center
The price is CA $135 per night
CA $135
CA $154 total
Aug 30 - Aug 31
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 City Dock and Annapolis Harbor Center Shopping Center are located nearby.
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
17.34 km from city center
The price is CA $150 per night
CA $150
CA $219 total
Aug 26 - Aug 27
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 Annapolis City Dock and Sandy Point State Park are located nearby.
Pet-friendly
Free WiFi
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 center
The price is CA $144 per night
CA $144
CA $165 total
Sep 7 - Sep 8
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 City Dock and Westfield Annapolis Mall are located nearby.
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
18.04 km from city center
The price is CA $214 per night
CA $214
CA $244 total
Aug 30 - Aug 31
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 City Dock and Sandy Point State Park are located nearby.
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 center
The price is CA $115 per night
CA $115
CA $127 total
Aug 31 - Sep 1
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.
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
Reserve now, pay when you stay
23.15 km from city center
The price is CA $139 per night
CA $139
CA $159 total
Sep 1 - Sep 2
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 Bowl 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
16.96 km from city center
The price is CA $296 per night
CA $296
CA $338 total
Aug 31 - Sep 1
includes taxes & fees
Book a stay at this business-friendly 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 Sandy Point State Park are located nearby.
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street Annapolis MD
18.24 km from city center
The price is CA $146 per night
CA $146
CA $166 total
Sep 7 - Sep 8
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 City Dock and Sandy Point State Park are located nearby.
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

3 out of 5
2559 Riva Rd Annapolis MD
22.83 km from city center
The price is CA $127 per night
CA $127
CA $144 total
Aug 31 - Sep 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 City Dock and Annapolis Harbor Center 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
1,194 hotels
Lowest Price
CA $127
Highest Price
CA $338
Popular hotels
DoubleTree by Hilton Hotel Annapolis, Historic Inns of Annapolis, Crowne Plaza Annapolis by IHG, Graduate by Hilton Annapolis, St Michaels Inn, Country Inn & Suites by Radisson, Annapolis, MD, Annapolis Waterfront Hotel, Autograph Collection, Hilton Garden Inn Annapolis Downtown, 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 $127 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 1,194 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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

4 out of 5
Posted 6 hours ago
Travelocity Verified Review
"I wish I could give half stars because this place is really a 4.5 stars. First off this place was great, it is everything you need for a hotel. Great prices, friendly staff, very clean, very nice hotel. Why I gave it 4 stars? The coffee machine was down for our first night, the jacuzzi was down for maintenance, the wifi went for maintenance lol so it was a little much but I know you can't always control those things. Another small thing, I also wish the TV's were smart TV's and I wish the rooms came with a microwave. Overall great hotel, would stay here again."
A verified traveller stayed at Crowne Plaza Annapolis by IHG
Crowne Plaza Annapolis by IHG