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Tonight

Apr 11 - Apr 12

Tomorrow night

Apr 12 - Apr 13

Next weekend

Apr 17 - Apr 19

Most frequently booked Chestertown hotels

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

Free cancellation

1.02 km from city centre

CA $154

CA $171 total

May 3 - May 4

includes taxes & fees

Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rolling Road Park and Larrabee Arts Center are located nearby.

Pool

Breakfast included

Blue Heron Farm Waterfront Chalet

Chestertown MD

11.37 km from city centre

Get rates

Stay at this farm stay in Chestertown. Enjoy a garden, laundry facilities, and patios. Popular attractions Chase Island and Crumpton Auction are located nearby.

Air conditioning

Parking available

Historic Inns of Annapolis

58 State Circle Annapolis MD

Free cancellation

Reserve now, pay when you stay

45.06 km from city centre

CA $179

CA $251 total

Apr 19 - Apr 20

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

Hampton Inn Baltimore/Glen Burnie

6617 Ritchie Hwy Glen Burnie MD

Free cancellation

Reserve now, pay when you stay

46.87 km from city centre

CA $129

CA $147 total

Apr 19 - Apr 20

includes taxes & fees

Book a stay at this business-friendly hotel in Glen Burnie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Baltimore Inner Harbor Marina and Oriole Park at Camden Yards are located nearby.

Breakfast included

Pet-friendly

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

4 Philadelphia Ct Rosedale MD

Free cancellation

Reserve now, pay when you stay

38.72 km from city centre

CA $103

CA $119 total

May 4 - May 5

includes taxes & fees

Book a stay at this business-friendly hotel in Rosedale. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions White Marsh Mall and Essex Marina are located nearby.

Breakfast included

Pet-friendly

Pendry Baltimore

1715 Thames St. Baltimore MD

Free cancellation

Reserve now, pay when you stay

45.57 km from city centre

CA $470

CA $609 total

May 3 - May 4

includes taxes & fees

Book a stay at this luxury hotel in Baltimore. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions Baltimore Inner Harbor Marina and National Aquarium in Baltimore are located nearby.

Pool

Spa

Best Western Plus Hotel & Conference Center

5625 O'Donnell Street Baltimore MD

Free cancellation

Reserve now, pay when you stay

41.74 km from city centre

CA $148

CA $173 total

Apr 19 - Apr 20

includes taxes & fees

Book a stay at this business-friendly hotel in Baltimore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Baltimore Inner Harbor Marina and National Aquarium in Baltimore are located nearby.

Pool

Hot tub

Annapolis Waterfront Hotel, Autograph Collection

80 Compromise St Annapolis MD

Free cancellation

Reserve now, pay when you stay

44.98 km from city centre

CA $316

CA $360 total

Apr 19 - Apr 20

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 Ego Alley and Susan Campbell Park are located nearby.

Pet-friendly

Free WiFi

Hilton Garden Inn Baltimore/White Marsh

5015 Campbell Boulevard Baltimore MD

Free cancellation

Reserve now, pay when you stay

37.61 km from city centre

CA $135

CA $156 total

May 10 - May 11

includes taxes & fees

Book a stay at this family-friendly hotel in Baltimore. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions White Marsh Mall and Essex Marina are located nearby.

Pool

Pet-friendly

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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 family friendly Chestertown hotel deals

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

CA $154

CA $171 total

May 3 - May 4

includes taxes & fees

8.6/10 Excellent! (896 reviews)

Top cheap Chestertown hotel deals

Driftwood Inn

609 Washington Avenue Chestertown MD

Get rates

5.2/10 (175 reviews)

Chestertown hotels essential information

Accommodation	1,046 hotels
Lowest Price	CA $119
Highest Price	CA $609
Popular hotels	Comfort Inn & Suites Chestertown, Blue Heron Farm Waterfront Chalet, Historic Inns of Annapolis, Hampton Inn Baltimore/Glen Burnie, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Pendry Baltimore, Best Western Plus Hotel & Conference Center, Annapolis Waterfront Hotel, Autograph Collection, Hilton Garden Inn Baltimore/White Marsh

Frequently asked questions

What are the top kid-friendly hotels in Chestertown?

From cool amenities to more room to move, kid-friendly hotels are equipped with features that can help transform an everyday family vacation into an extraordinary one. These Chestertown options make getting away with the youngsters a snap: The whole team will enjoy their time at Driftwood Inn. Pet-friendly facilities and front desk services are just a few of the things that help make this property a sought-after option. Carriage House Hideaway in Middle of Chestertown is another excellent choice. After a fun day of exploring, return to your cozy room and perks like a playground and animal viewing activities.

Where can I find cheap hotels in Chestertown?

At Travelocity you'll find really nice hotels in Chestertown 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 Chestertown rather than in Chestertown. We may find you even better rates, too.

How do I find the best Chestertown hotel deals?

Simple! On Travelocity, look through the fantastic offers we've already found in Chestertown 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 Chestertown?

The cheapest hotel in Chestertown is CA $119 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 Chestertown?

There are 1,046 hotels in Chestertown on Travelocity.

What are the best hotels in Chestertown?

Chestertown 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 Chestertown for you!

When is the best time to visit Chestertown?

If you want the joy of a fun-filled trip in peak season, visit Chestertown during February, March and October. If you'd prefer the peace of off-season, book a stay during quieter months, such as May, November and December.

When is the cheapest time to stay in Chestertown?

Based on historic data is usually the cheapest month to visit Chestertown. 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 Chestertown?

There are multiple hotels in Chestertown 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 Chestertown. We have plenty of kid-friendly hotels in Chestertown to choose from on Travelocity!

Why book a hotel in Chestertown through Travelocity?

Because we have the top hotels in Chestertown! 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 Chestertown 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 Chestertown hotel reviews by fellow wanderers

Historic Inns of Annapolis

5 out of 5

Posted 7 hours ago

Travelocity Verified Review

"Perfect location to explore history and walking distance to everything! Superior service from friendly, professional staff. Clean and comfortable rooms. Thank you!"

A verified traveller stayed at Historic Inns of Annapolis