Photo by Patricia Knorr

Chestertown Hotels from S$77

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Chestertown hotels

Our top choices for Chestertown hotels

Super 8 by Wyndham Havre De Grace Aberdeen Area

2.0 star property
6.6 out of 10, (943)
"Front desk lady was super friendly helpfull dollor general close clean room great value"
The price is S$84
includes taxes & fees
27 Aug - 28 Aug
Super 8 by Wyndham Havre De Grace Aberdeen Area

Days Inn by Wyndham Aberdeen

2.0 star property
7.0 out of 10, Good, (884)
"Great price, nice staff. "
The price is S$93
includes taxes & fees
24 Aug - 25 Aug
Days Inn by Wyndham Aberdeen

Travelodge by Wyndham Aberdeen

2.0 star property
6.2 out of 10, (506)
"Great location "
The price is S$78
includes taxes & fees
24 Aug - 25 Aug
Travelodge by Wyndham Aberdeen

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (387)
"Good location."
The price is S$103
includes taxes & fees
28 Aug - 29 Aug
Red Roof Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (797)
"It was a clean comfortable spot to rest for the night. "
The price is S$156
includes taxes & fees
7 Sept - 8 Sept
Comfort Inn & Suites Chestertown

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (65)
"Great place to get some quiet rest by the water"
The price is S$189
includes taxes & fees
24 Aug - 25 Aug
The Lodge at Great Oak Landing

SpringHill Suites Baltimore White Marsh/Middle River

2.5 star property
9.0 out of 10, Wonderful, (723)
"Love this place"
The price is S$182
includes taxes & fees
24 Aug - 25 Aug
SpringHill Suites Baltimore White Marsh/Middle River

Super 8 by Wyndham Aberdeen MD

2.0 star property
6.8 out of 10, (835)
"Everything is good for a business trip, simply sleep"
The price is S$78
includes taxes & fees
7 Sept - 8 Sept
Super 8 by Wyndham Aberdeen MD

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (823)
"Staff was pleasant…room was clean, comfortable and very quiet. Good choice…nice stay."
The price is S$156
includes taxes & fees
27 Aug - 28 Aug
Hampton Inn Middletown

Motel Edgewood

2.0 star property
8.6 out of 10, Excellent, (7)
"Bed was clean and crisply made. Occupants were respectful of sleeping hours. Check-in and check-out were simple. Parking was convenient and had easy access to the highway."
The price is S$80
includes taxes & fees
24 Aug - 25 Aug
Motel Edgewood

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (606)
"Very beautiful and clean properly with great staff. "
The price is S$153
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (890)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is S$170
includes taxes & fees
24 Aug - 25 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG

Comfort Inn & Suites Aberdeen near APG

2.5 star property
7.8 out of 10, Good, (752)
"Wonderful stay "
The price is S$133
includes taxes & fees
24 Aug - 25 Aug
Comfort Inn & Suites Aberdeen near APG

Red Roof Inn Aberdeen

2.0 star property
6.4 out of 10, (1001)
"Affordable and comfortable stay for one night. Microwave in the rm was a plus"
The price is S$79
includes taxes & fees
24 Aug - 25 Aug
Red Roof Inn Aberdeen

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

3.0 star property
8.2 out of 10, Very good, (1003)
"Good hotel, good location "
The price is S$103
includes taxes & fees
24 Aug - 25 Aug
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Holiday Inn Belcamp - Aberdeen Area by IHG

3.0 star property
8.4 out of 10, Very good, (711)
"I liked the breakfast, I didn’t like how noisy it was one night with kids screaming and running around, I didn’t like that towels and cups were not replaced each day."
The price is S$158
includes taxes & fees
29 Aug - 30 Aug
Holiday Inn Belcamp - Aberdeen Area by IHG

Hampton Inn Baltimore/White Marsh

2.5 star property
7.6 out of 10, Good, (1001)
"Clean area clean rooms friendly staff"
The price is S$129
includes taxes & fees
2 Sept - 3 Sept
Hampton Inn Baltimore/White Marsh

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (86)
"Owner was very nice. "
The price is S$127
includes taxes & fees
24 Aug - 25 Aug
Relax Inn Smyrna

Village Inn

2.0 star property
6.2 out of 10, (492)
"The staff is super friendly and there is a convenient store to buy drinks and snacks within walking distance."
The price is S$135
includes taxes & fees
25 Aug - 26 Aug
Village Inn

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (612)
"Great place to stay. "
The price is S$237
includes taxes & fees
16 Sept - 17 Sept
Hyatt Place Kent Narrows & Marina
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.
Save an average of 15% on thousands of hotels when you're signed in

Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

Photo by Assya A
Open Photo by Assya A

Top Chestertown Hotel Reviews

Frequently asked questions

Where is the best place for a stay in Chestertown?

Comfort Inn & Suites Chestertown is a favourite property for Expedia customers. This hotel offers free breakfast and free parking. Reviews from our site also recommend Red Roof Inn & Suites Chestertown and Driftwood Inn as top options for your stay. See all available top hotels, or vacation rentals in Chestertown.

If I need to cancel my hotel reservation in Chestertown, will I receive a refund?

Yes! You'll find that most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chestertown.

What's the best family accommodation in Chestertown?

Comfort Inn & Suites Chestertown is a hotel with free parking and free full breakfast, and it's a top choice on Expedia for families. Red Roof Inn & Suites Chestertown is another good option for your stay with the kids. Also, children of all ages will enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.

What is the top LGBTQ-friendly hotel in Chestertown?

Comfort Inn & Suites Chestertown is a top LGBTQ-friendly hotel, and features free breakfast and free WiFi. Red Roof Inn & Suites Chestertown and The Lodge at Great Oak Landing are two other good options for your stay. See all available hotels listed as LGBTQ-friendly in Chestertown.

What's the best dog-friendly accommodation option in Chestertown?

Comfort Inn & Suites Chestertown is a top hotel for people travelling with their pets, and offers a seasonal outdoor pool and a fitness centre for its human guests. Other good options for you and your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn. See more pet-friendly hotel accommodations in Chestertown.

What's the best hotel to stay near the beach in Chestertown?

The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool and 3 bars/lounges, and it's located near a private beach . See more stays near the beach in Chestertown.

What are some accommodation options with pools in Chestertown?

The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool, 3 bars/lounges and free WiFi. View all hotels with pools in Chestertown.

How is it to stay in Chestertown?

Visitors to Chestertown will definitely enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals and art. In Chestertown, there are 44 hotels and other accommodation options to choose from. Find out more about Chestertown.

What should I see while I'm in Chestertown?

Cultural venues include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. A couple of additional sights to add to your itinerary are Rolphs Wharf Marina and Chestertown Historic District. Take a look at what more there is to see and do in Expedia's Chestertown guide.

What's the seasonal weather like in Chestertown?

The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.