Chestertown Hotels

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Our top choices for Chestertown hotels

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 €105
includes taxes & fees
19 Apr - 20 Apr
The Lodge at Great Oak Landing

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (435 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 €67
includes taxes & fees
22 Apr - 23 Apr
Red Roof Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (898 reviews)
"Best place to stay always "
United States
Robert
The price is €104
includes taxes & fees
26 Apr - 27 Apr
Comfort Inn & Suites Chestertown

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is €146
includes taxes & fees
22 Apr - 23 Apr
Haven Point Inn and Gallery

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
"Beautiful hotel, nice staff"
United States
Kim
The price is €147
includes taxes & fees
20 Apr - 21 Apr
Kent Island Resort

Relax Inn Smyrna

Relax Inn Smyrna
2.0 star property
Smyrna
8.0 out of 10, Very good, (94 reviews)
"Great location"
United States
Patrick
The price is €91
includes taxes & fees
16 Apr - 17 Apr
Relax Inn Smyrna

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,000 reviews)
"My visit at the Hotel was amazing & peaceful."
United States
Milton
The price is €76
includes taxes & fees
22 Apr - 23 Apr
Quality Inn Smyrna

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (542 reviews)
"As always we loved our stay! Definitely will be coming back "
United States
John
The price is €127
includes taxes & fees
19 Apr - 20 Apr
Vandiver Inn

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (62 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
United States
Sandra
The price is €132
includes taxes & fees
22 Apr - 23 Apr
Inn at Huntingfield Creek

Motel Edgewood

Motel Edgewood
2.0 star property
Edgewood
8.0 out of 10, Very good, (12 reviews)
"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."
United States
Nancy
The price is €51
includes taxes & fees
29 Apr - 30 Apr
Motel Edgewood

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)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is €94
includes taxes & fees
28 Apr - 29 Apr
Best Western Kent Narrows Inn

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (369 reviews)
"Clean room, felt very safe and secure, free parking, staff very friendly, plenty of eating and shopping close by"
United States
Taneica
The price is €106
includes taxes & fees
28 Apr - 29 Apr
Fairfield Inn & Suites by Marriott Middletown

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (675 reviews)
"Great location and nice place to stay. Walk to nearby things to do and enjoy. "
United States
Sharon
The price is €95
includes taxes & fees
19 Apr - 20 Apr
Holiday Inn Express & Suites Middletown by IHG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1,012 reviews)
"Near $95 and good place to stay"
United States
Thandavarayan
The price is €84
includes taxes & fees
28 Apr - 29 Apr
La Quinta Inn & Suites by Wyndham Aberdeen-APG

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
2.0 star property
North East
8.8 out of 10, Excellent, (3 reviews)
"Very nice cabin. By the town and easy drive to everything. "
United States
Mark
The price is €359
includes taxes & fees
19 Apr - 20 Apr
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (363 reviews)
"Staff was very friendly and it was a perfect location for us"
United States
Ryan
The price is €93
includes taxes & fees
26 Apr - 27 Apr
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (891 reviews)
"Staff was nice and room was clean "
United States
Lauren
The price is €100
includes taxes & fees
22 Apr - 23 Apr
Quality Inn Grasonville near Kent Island

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, (981 reviews)
"Cleaning lady and front desk were very frindly, helpful, speedy & great at there job."
United States
Mary
The price is €49
includes taxes & fees
19 Apr - 20 Apr
Super 8 by Wyndham Havre De Grace Aberdeen Area

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (636 reviews)
"Friendly and clean, great staff!"
United States
Sharon
The price is €90
includes taxes & fees
3 May - 4 May
Hampton Inn & Suites Baltimore/Aberdeen

Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG
2.5 star property
Aberdeen
8.0 out of 10, Very good, (880 reviews)
"Would stay again! Very great place "
United States
Mindy
The price is €73
includes taxes & fees
26 Apr - 27 Apr
Comfort Inn & Suites Aberdeen near APG
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

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.

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

Top Chestertown Hotel Reviews

More cheap stays in Chestertown

Frequently asked questions

Where is the best place for a stay in Chestertown?
Based on our traveller data, Comfort Inn & Suites Chestertown is one of the top choices for your stay. This hotel offers free breakfast and free parking. Other good options for your trip to the area are Blue Heron Farm Waterfront Chalet and Historic Inns of Annapolis. See all available top hotels, or vacation rentals in Chestertown.
What are some of the best holiday rentals that Chestertown has to offer?
Captivating Chesapeake experience: This holiday home rental outside of Chestertown is located on the waterfront, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of books. See all 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 43 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 Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland. 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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