Chestertown Hotels from S$72

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Check prices for these dates

Tonight
25 Feb - 26 Feb
Tomorrow
26 Feb - 27 Feb
This weekend
27 Feb - 1 Mar
Next weekend
6 Mar - 8 Mar

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Our top choices for Chestertown hotels

Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77 reviews)
"Very nice rooms, "
United States
Stephania
The price is S$156
includes taxes & fees
26 Mar - 27 Mar
The Lodge at Great Oak Landing
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (427 reviews)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
The price is S$112
includes taxes & fees
26 Feb - 27 Feb
Red Roof Inn & Suites Chestertown
Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (879 reviews)
"Polite and kind hotel manager"
United States
Richard
The price is S$142
includes taxes & fees
8 Mar - 9 Mar
Comfort Inn & Suites Chestertown
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (535 reviews)
"a wonderful place to stay with super friendly staff. easy walks to downtown and restaurants. stayed here before and definitely will be back"
United States
Dieter
Vandiver Inn
Property amenity

Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.6 out of 10, (975 reviews)
"There were no healthy options offered, not even hard-boiled eggs. I guess they haven't seen the new food pyramid!"
United States
Carleen Lyden
The price is S$73
includes taxes & fees
1 Mar - 2 Mar
Super 8 by Wyndham Havre De Grace Aberdeen Area
Free continental breakfast

Holiday Inn Express White Marsh by IHG

Holiday Inn Express White Marsh by IHG
2.5 star property
Nottingham
9.4 out of 10, Exceptional, (1,009 reviews)
"We loved our stay here! Bed and pillows were clean and comfy, hot breakfast had all the necessities, and rooms were very nice! "
United States
Madyn
The price is S$155
includes taxes & fees
1 Mar - 2 Mar
Holiday Inn Express White Marsh by IHG
View from property

TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen
3.0 star property
Aberdeen
9.2 out of 10, Wonderful, (106 reviews)
"Clean room and attentive staff ."
United States
Stephen
The price is S$187
includes taxes & fees
27 Feb - 28 Feb
TownePlace Suites by Marriott Edgewood Aberdeen
Terrace/patio

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (718 reviews)
"Amazing location and staff!"
United States
Bobbi J.
The price is S$159
includes taxes & fees
3 Mar - 4 Mar
Hyatt Place Kent Narrows & Marina
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (875 reviews)
"Nice staff and rooms"
United States
Walter
The price is S$118
includes taxes & fees
8 Mar - 9 Mar
Quality Inn Grasonville near Kent Island
Lake

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (61 reviews)
"Quiet. Friendly staff. Beautiful grounds. Very clean."
United States
Brian
Inn at Huntingfield Creek
Front of property – evening/night

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (437 reviews)
"Amazing rooms and service!"
United States
Alicia
The price is S$266
includes taxes & fees
1 Mar - 2 Mar
The Inn at Chesapeake Bay Beach Club
In-room safe, individually furnished, desk, laptop workspace

Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG
2.5 star property
Bel Air
8.0 out of 10, Very good, (487 reviews)
"The staff is great, roon clean & spacious"
United States
Thomas
The price is S$119
includes taxes & fees
27 Feb - 28 Feb
Candlewood Suites Aberdeen-Bel Air by IHG
Bar (on property)

Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (245 reviews)
"Very friendly staff and easy check in."
United States
Kurt
The price is S$150
includes taxes & fees
5 Mar - 6 Mar
Hilton Garden Inn Bel Air
Desk, iron/ironing board, free cots/infant beds, free WiFi

Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
Essex
5.6 out of 10, (431 reviews)
"Mice and all kind of bugs had to buy blankets to sleep on from the people staying there looked like a halfway house very disappointed coming from Expedia I trust your company on all my business trips I will start checking the reviews. Sorry to say but that was a waist of had money."
United States
Emanuel
The price is S$95
includes taxes & fees
2 Mar - 3 Mar
Super 8 by Wyndham Baltimore/Essex Area
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"Nice breakfast, cleanroom. Great location."
United States
Wayne
The price is S$132
includes taxes & fees
15 Mar - 16 Mar
Best Western Kent Narrows Inn
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (963 reviews)
"Clean room, I enjoy staying here every time I'm in the area"
United States
Peter
The price is S$134
includes taxes & fees
22 Mar - 23 Mar
Holiday Inn Express Annapolis East-Kent Island by IHG
Desk, laptop workspace, iron/ironing board, free WiFi

SpringHill Suites by Marriott Edgewood/Aberdeen

SpringHill Suites by Marriott Edgewood/Aberdeen
3.0 star property
Bel Air
8.8 out of 10, Excellent, (369 reviews)
"Staff was very courteous "
United States
Tina
The price is S$156
includes taxes & fees
8 Mar - 9 Mar
SpringHill Suites by Marriott Edgewood/Aberdeen
Restaurant

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (226 reviews)
"Had a very pleasant check in with this hotel. Many restaurants are within a mile of the hotel. Very close to I-95. "
United States
Dennis
The price is S$119
includes taxes & fees
22 Mar - 23 Mar
Courtyard Aberdeen at Ripken Stadium
Terrace/patio

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,000 reviews)
"Staff was friendly and rooms were clean. Beautiful area to visit. "
United States
Amy
The price is S$149
includes taxes & fees
2 Mar - 3 Mar
Hilton Garden Inn Kent Island Marina
Terrace/patio

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (313 reviews)
"Always consistent and great staff!"
United States
Linda
The price is S$155
includes taxes & fees
23 Mar - 24 Mar
Fairfield Inn & Suites by Marriott Aberdeen
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.
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Stay near popular Chestertown attractions

Washington College

4.1/5 (45 reviews)
Founded in 1782, Washington College is the first college chartered in the sovereign United States. Explore its picturesque campus with historic architecture and Chester River waterfront views.
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Historical Society of Kent County Maryland

Step inside the Geddes-Piper House, home to Kent County's historical treasures and curated exhibits. Explore Maryland's rich past through intimate galleries and knowledgeable guides who bring local stories to life.
See properties

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.

See all hotels in Chestertown
Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Room was clean and quiet… will definitely return "
Kelly 1-night trip
Posted 23 hours ago
Best Western Plus Hotel & Conference Center

More cheap stays in Chestertown

Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

1709 Edgewood Road Edgewood MD
The price is S$72 per night from 26 Feb to 27 Feb
S$72
26 Feb - 27 Feb
includes taxes & fees
5.8/10 (1,000 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. Red Roof Inn & Suites Chestertown is another top choice for your stay based on reviews. 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 39 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. The picturesque setting of Northern Chesapeake Bay and Chesapeake Bay exemplify the area's natural beauty. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. 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.

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