Book Cheap Hotels in Chestertown

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Check hotel availability in Chestertown

Tonight
Check prices in Chestertown for tonight, Dec 6 - Dec 7
Dec 6 - Dec 7
Tomorrow night
Check prices in Chestertown for tomorrow night, Dec 7 - Dec 8
Dec 7 - Dec 8
Next weekend
Check prices in Chestertown for next weekend, Dec 12 - Dec 14
Dec 12 - Dec 14

Most frequently booked Chestertown hotels

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Free cancellation
Reserve now, pay when you stay
1.02 km from city centre
The price is CA $142 per night
CA $142
CA $158 total
Dec 25 - Dec 26
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 Historical Society of Kent County Maryland are located nearby.
Pool
Breakfast included
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
Free cancellation
Reserve now, pay when you stay
0.93 km from city centre
The price is CA $99 per night
CA $99
CA $110 total
Dec 13 - Dec 14
includes taxes & fees
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Rolling Road Park and Historical Society of Kent County Maryland are located nearby.
Pet-friendly
Parking included
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd Chestertown MD
Free cancellation
12.5 km from city centre
The price is CA $138 per night
CA $138
CA $158 total
Dec 7 - Dec 8
includes taxes & fees
Book a stay at this beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point Drive are located nearby.
Pool
Parking included
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

2.5 out of 5
6617 Ritchie Hwy Glen Burnie MD
Free cancellation
Reserve now, pay when you stay
46.87 km from city centre
The price is CA $128 per night
CA $128
CA $146 total
Dec 15 - Dec 16
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
Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
Free cancellation
Reserve now, pay when you stay
45.57 km from city centre
The price is CA $447 per night
CA $447
CA $582 total
Dec 23 - Dec 24
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
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
Free cancellation
Reserve now, pay when you stay
45.01 km from city centre
The price is CA $248 per night
CA $248
CA $283 total
Dec 14 - Dec 15
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
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
45.06 km from city centre
Get rates
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
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 out of 5
5625 O'Donnell Street Baltimore MD
Free cancellation
Reserve now, pay when you stay
41.74 km from city centre
The price is CA $123 per night
CA $123
CA $144 total
Dec 14 - Dec 15
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 Baltimore Cruise Terminal are located nearby.
Pool
Hot tub
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

3 out of 5
5015 Campbell Boulevard Baltimore MD
Free cancellation
Reserve now, pay when you stay
37.61 km from city centre
The price is CA $132 per night
CA $132
CA $152 total
Dec 26 - Dec 27
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

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD
The price is CA $142 per night from Dec 25 to Dec 26
CA $142
CA $158 total
Dec 25 - Dec 26
includes taxes & fees
8.4/10 Very Good! (857 reviews)

Top cheap Chestertown hotel deals

Driftwood Inn

Driftwood Inn

609 Washington Avenue Chestertown MD
The price is CA $88 per night from Jan 5 to Jan 6
CA $88
CA $97 total
Jan 5 - Jan 6, 2026
includes taxes & fees
5/10 (175 reviews)

Chestertown hotels essential information

Accommodation
1,086 hotels
Lowest Price
CA $97
Highest Price
CA $582
Popular hotels
Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing, Hampton Inn Baltimore/Glen Burnie, Pendry Baltimore, Annapolis Waterfront Hotel, Autograph Collection, Historic Inns of Annapolis, Best Western Plus Hotel & Conference Center, 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 $97 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 1,086 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

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

5 out of 5
Posted 3 hours ago
Travelocity Verified Review
"😀😀😀😀😀😀😀😀"
A verified traveller stayed at Best Western Plus Hotel & Conference Center
Best Western Plus Hotel & Conference Center

Hotels near…

Areas of Chestertown