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Check prices for these dates

Tonight
5 Apr - 6 Apr
Tomorrow
6 Apr - 7 Apr
Next weekend
10 Apr - 12 Apr
In two weeks
17 Apr - 19 Apr

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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 NZ$217
includes taxes & fees
6 Apr - 7 Apr
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, (433 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 NZ$140
includes taxes & fees
3 May - 4 May
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, (894 reviews)
"Best place to stay always "
United States
Robert
The price is NZ$242
includes taxes & fees
19 Apr - 20 Apr
Comfort Inn & Suites Chestertown
Front of property – evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (175 reviews)
"Rooms are clean, staf was helpful "
United States
Daryl
The price is NZ$124
includes taxes & fees
1 May - 2 May
Driftwood Inn
Exterior

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is NZ$290
includes taxes & fees
21 Apr - 22 Apr
Haven Point Inn and Gallery
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (135 reviews)
"Beautiful hotel, nice staff"
United States
Kim
The price is NZ$276
includes taxes & fees
14 Apr - 15 Apr
Kent Island Resort
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,002 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is NZ$194
includes taxes & fees
12 Apr - 13 Apr
Best Western Kent Narrows Inn
Suite, 1 Queen Bed, Non Smoking

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (887 reviews)
"Staff was nice and room was clean "
United States
Lauren
The price is NZ$191
includes taxes & fees
7 Apr - 8 Apr
Quality Inn Grasonville near Kent Island
Deluxe Room | Interior detail

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 NZ$176
includes taxes & fees
8 Apr - 9 Apr
Relax Inn Smyrna
Exterior

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, (1,001 reviews)
"Near $95 and good place to stay"
United States
Thandavarayan
The price is NZ$174
includes taxes & fees
13 Apr - 14 Apr
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (538 reviews)
"As always we loved our stay! Definitely will be coming back "
United States
John
The price is NZ$238
includes taxes & fees
8 Apr - 9 Apr
Vandiver Inn
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (92 reviews)
"The room was over the garage. You couldn’t stand up in half the room as the ceiling was too low. Multiple tripping areas walking into and out of the space. No heat in bathroom. You have to walk to the front of house to enter for coffee in the morning. They have the nerve to charge you to park at the house. "
United States
Richard
The price is NZ$349
includes taxes & fees
6 Apr - 7 Apr
Flag House Inn
Exterior

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (583 reviews)
"Clean room, friendly staff, good food, excellent!"
United States
Dwayne
The price is NZ$181
includes taxes & fees
9 Apr - 10 Apr
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Standard Room, 2 Queen Beds

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, (979 reviews)
"Cleaning lady and front desk were very frindly, helpful, speedy & great at there job."
United States
Mary
The price is NZ$106
includes taxes & fees
12 Apr - 13 Apr
Super 8 by Wyndham Havre De Grace Aberdeen Area
Lake

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 NZ$352
includes taxes & fees
5 May - 6 May
Inn at Huntingfield Creek
Exterior

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
9.8 out of 10, Exceptional, (34 reviews)
"Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff"
United States
Ian
The price is NZ$345
includes taxes & fees
6 Apr - 7 Apr
134 Prince - Luxury Boutique Hotel
Terrace/patio

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, (359 reviews)
"Staff was very friendly and it was a perfect location for us"
United States
Ryan
The price is NZ$200
includes taxes & fees
12 Apr - 13 Apr
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Desk, laptop workspace, iron/ironing board, free WiFi

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,001 reviews)
"My visit at the Hotel was amazing & peaceful."
United States
Milton
The price is NZ$150
includes taxes & fees
5 May - 6 May
Quality Inn Smyrna
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, (325 reviews)
"The staff was lovely and so accommodating. Definitely the best part of our stay."
United States
Maritza
The price is NZ$215
includes taxes & fees
12 Apr - 13 Apr
Fairfield Inn & Suites by Marriott Aberdeen
Reception

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,005 reviews)
"Clean room, nice staff and great breakfast "
United States
Curtis
The price is NZ$176
includes taxes & fees
20 Apr - 21 Apr
Hampton Inn & Suites Edgewood/Aberdeen-South
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

4.3/5 (87 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

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

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

6/10 Okay
"Hot water doesn’t work well. Problems with flushing toilet; water pressure just didn’t seem strong. "
Daniel 2-night trip
Posted 5 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

More cheap accommodation in Chestertown

Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

1709 Edgewood Road Edgewood MD
The price is NZ$117 per night from 7 Apr to 8 Apr
NZ$117
7 Apr - 8 Apr
includes taxes & fees
5.8/10 (1,001 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.
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 42 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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