Chestertown Hotels from S$74

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11 Jan - 12 Jan
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12 Jan - 13 Jan
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16 Jan - 18 Jan
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23 Jan - 25 Jan

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Our top choices for Chestertown hotels

Lobby lounge
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (426 reviews)
"Clean and friendly staff. Good location."
United States
Robert
The price is S$103
includes taxes & fees
18 Jan - 19 Jan
Red Roof Inn & Suites Chestertown
Free daily full breakfast
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (866 reviews)
"Everything was well!"
United States
Ahmed
The price is S$146
includes taxes & fees
1 Feb - 2 Feb
Comfort Inn & Suites Chestertown
In-room safe, desk, soundproofing, rollaway beds
Super 8 by Wyndham Havre De Grace Aberdeen Area

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, (969 reviews)
"It's was satisfactory "
United States
John
The price is S$77
includes taxes & fees
18 Jan - 19 Jan
Super 8 by Wyndham Havre De Grace Aberdeen Area
Exterior detail
Vandiver Inn

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (533 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
Desk, laptop workspace, iron/ironing board, free WiFi
SpringHill Suites by Marriott Edgewood/Aberdeen

SpringHill Suites by Marriott Edgewood/Aberdeen

SpringHill Suites by Marriott Edgewood/Aberdeen
3.0 star property
Bel Air
8.8 out of 10, Excellent, (364 reviews)
"I usually like staying at SpringHill Suites locations. While this location was absolutely clean, quiet and the staff was great, the facility itself was a bit run down- cracks in the sink, etc. "
United States
Katharine
The price is S$159
includes taxes & fees
19 Jan - 20 Jan
SpringHill Suites by Marriott Edgewood/Aberdeen
Exterior
Candlewood Suites Aberdeen-Bel Air by IHG

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, (478 reviews)
"The staff is great, roon clean & spacious"
United States
Thomas
The price is S$120
includes taxes & fees
14 Jan - 15 Jan
Candlewood Suites Aberdeen-Bel Air by IHG
Reception
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130 reviews)
"Beautiful and peaceful property!"
United States
Jerry
The price is S$226
includes taxes & fees
18 Jan - 19 Jan
Kent Island Resort
Bar (on property)
Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (238 reviews)
"Kind staff, very clean. Lovely stay!"
Canada
Michelle
The price is S$141
includes taxes & fees
23 Jan - 24 Jan
Hilton Garden Inn Bel Air
In-room safe, iron/ironing board, free WiFi, bed sheets
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (867 reviews)
"Great hotel. Stayed multiple times at this location "
United States
Nicholas
The price is S$123
includes taxes & fees
19 Jan - 20 Jan
Quality Inn Grasonville near Kent Island
View from property
TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (101 reviews)
"Clean room and attentive staff ."
United States
Stephen
The price is S$172
includes taxes & fees
12 Jan - 13 Jan
TownePlace Suites by Marriott Edgewood Aberdeen
Lake
Inn at Huntingfield Creek

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (59 reviews)
"Quiet. Friendly staff. Beautiful grounds. Very clean."
United States
Brian
Inn at Huntingfield Creek
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (697 reviews)
"Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. "
United States
Kevin
The price is S$173
includes taxes & fees
19 Jan - 20 Jan
Hyatt Place Kent Narrows & Marina
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (950 reviews)
"Great staff, clean room, nice view!"
United States
Quiana
The price is S$136
includes taxes & fees
19 Jan - 20 Jan
Holiday Inn Express Annapolis East-Kent Island by IHG
Front of property – evening/night
The Inn at Chesapeake Bay Beach Club

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, (433 reviews)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
United States
Rery
The price is S$269
includes taxes & fees
18 Jan - 19 Jan
The Inn at Chesapeake Bay Beach Club
Exterior
Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
Essex
5.6 out of 10, (418 reviews)
"Good"
United States
Carlos
The price is S$104
includes taxes & fees
13 Jan - 14 Jan
Super 8 by Wyndham Baltimore/Essex Area
Indoor pool
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,002 reviews)
"Nice breakfast, cleanroom. Great location."
United States
Wayne
The price is S$119
includes taxes & fees
18 Jan - 19 Jan
Best Western Kent Narrows Inn
Lobby
Homewood Suites by Hilton Bel Air

Homewood Suites by Hilton Bel Air

Homewood Suites by Hilton Bel Air
3.0 star property
Bel Air
8.8 out of 10, Excellent, (450 reviews)
"Very welcoming stuff. Clean room at the exception of the Sofa, it has pets hair!"
Canada
Mohamed
The price is S$135
includes taxes & fees
17 Jan - 18 Jan
Homewood Suites by Hilton Bel Air
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,004 reviews)
"Clean and friendly staff"
United States
Lisa
The price is S$175
includes taxes & fees
18 Jan - 19 Jan
Hilton Garden Inn Kent Island Marina
Lobby lounge
SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
2.5 star property
Middle River
9.0 out of 10, Wonderful, (783 reviews)
"Thank you for another great stay at Spring Hill Suites"
United States
Melissa
The price is S$159
includes taxes & fees
18 Jan - 19 Jan
SpringHill Suites Baltimore White Marsh/Middle River
Desk, iron/ironing board, free WiFi, bed sheets
Extended Stay America Suites Baltimore Bel Air Aberdeen

Extended Stay America Suites Baltimore Bel Air Aberdeen

Extended Stay America Suites Baltimore Bel Air Aberdeen
2.5 star property
Bel Air
7.0 out of 10, Good, (712 reviews)
"Reasonable for the location . "
United States
Shannandoah
The price is S$106
includes taxes & fees
14 Jan - 15 Jan
Extended Stay America Suites Baltimore Bel Air 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)
Enjoy the student vibe when you visit Washington College during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
See properties

Wilmer Park

Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"H"
William 2-night trip
Posted 4 days ago
Historic Inns of Annapolis

More cheap stays in Chestertown

Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

1709 Edgewood Road Edgewood MD
The price is S$74 per night from 12 Jan to 13 Jan
S$74
12 Jan - 13 Jan
includes taxes & fees
5.6/10 (999 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 40 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. Natural beauty is on display at Northern Chesapeake Bay, Chesapeake Bay and Chestertown Dog Park. 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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