Photo by Patricia Knorr

Search Chestertown hotels

    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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
24 Jul - 25 Jul
Tomorrow
25 Jul - 26 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Filter by

Guest rating
Guest rating
Property class

Top hotels and accommodation in Chestertown

The Lodge at Great Oak Landing
Relax by the pool surrounded by lounge chairs and a deck.

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (55)
"Great place to get some quiet rest by the water"
The price is NZ$237
includes taxes & fees
27 July - 28 July
The Lodge at Great Oak Landing
Comfort Inn & Suites Chestertown
Welcome to our reception area, where friendly staff are available to assist with your stay.

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (786)
"It was a clean comfortable spot to rest for the night. "
The price is NZ$210
includes taxes & fees
17 Aug - 18 Aug
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Classic hotel room with a large bed, bedside tables, and a comfortable armchair.

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (379)
"Good location."
The price is NZ$140
includes taxes & fees
3 Aug - 4 Aug
Red Roof Inn & Suites Chestertown
Driftwood Inn
Rows of rooms with stone facades and windows line the building's side.

Driftwood Inn

2.0 star property
5.2 out of 10, (171)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is NZ$117
includes taxes & fees
3 Aug - 4 Aug
Driftwood Inn
Quality Inn
Quality Inn features a modern architectural design with a flat roof and symmetrical facade, accessible via a covered walkway.

Quality Inn

2.5 star property
7.6 out of 10, Good, (1003)
"A solid, comfortable place to stay at a reasonable rate."
The price is NZ$185
includes taxes & fees
4 Aug - 5 Aug
Quality Inn
Relax Inn Smyrna
Commercial building with a brick facade and flat roof, featuring an office entrance and a service entrance.

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (84)
"Owner was very nice. "
The price is NZ$147
includes taxes & fees
7 Aug - 8 Aug
Relax Inn Smyrna
Hampton Inn Middletown
Guests can dine in comfort at this hotel's spacious dining area, surrounded by six chairs and a large window with sheer curtains.

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (817)
"Front desk service was exceptional!!"
The price is NZ$239
includes taxes & fees
20 Aug - 21 Aug
Hampton Inn Middletown
Holiday Inn Express And Suites Middletown by IHG
Relax in our stylish lobby with a seating area, reception desk, and digital display.

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (594)
"Easy to navigate and nice, helpful staff "
The price is NZ$239
includes taxes & fees
6 Aug - 7 Aug
Holiday Inn Express And Suites Middletown by IHG
Fairfield Inn & Suites by Marriott Middletown
Experience the grand entrance of this hotel, featuring a covered walkway and stone pillars, surrounded by a beautifully manicured lawn and ample parking.

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (255)
"Nice place to stay"
The price is NZ$193
includes taxes & fees
3 Aug - 4 Aug
Fairfield Inn & Suites by Marriott Middletown
Quality Inn
Relax in a comfortable seating area with a sofa and armchairs, and enjoy a view of the outside from the large window.

Quality Inn

2.5 star property
7.8 out of 10, Good, (793)
"The place was clean and quiet, staff was great, not much nearby to see and do. It’s a fishing town. "
The price is NZ$180
includes taxes & fees
24 Aug - 25 Aug
Quality Inn
Vandiver Inn
Step into a charming Victorian-style entrance surrounded by lush greenery and ornate details.

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (505)
"Loved our visit and will be back again. The rooms were comfortable and breakfast was great, and very convenient to everything "
Vandiver Inn
Super 8 by Wyndham Havre De Grace Aberdeen Area
Two beds with matching headboards, a desk, and a window with city views.

Super 8 by Wyndham Havre De Grace Aberdeen Area

2.0 star property
6.8 out of 10, (928)
"This is a terrible place to stay. "
The price is NZ$98
includes taxes & fees
5 Aug - 6 Aug
Super 8 by Wyndham Havre De Grace Aberdeen Area
Hilton Garden Inn Kent Island Marina
Relax on the outdoor terrace with a view of the marina, surrounded by wicker furniture and beautiful flowers.

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (965)
"Great spot with beautiful views. "
The price is NZ$298
includes taxes & fees
28 July - 29 July
Hilton Garden Inn Kent Island Marina
Holiday Inn Express Annapolis East-Kent Island by IHG
Welcome to the Holiday Inn Express, where guests can check in and enjoy a convenient stay.

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (874)
"Great place"
The price is NZ$277
includes taxes & fees
31 July - 1 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG
Best Western Kent Narrows Inn
Two single beds with white linens and dark wood headboard, flat-screen TV, and a dresser with drawers.

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1006)
"Second time staying, it’s priced right, great staff, and amazing restaurants right across the street, quiet area right by the bay bridge. "
The price is NZ$231
includes taxes & fees
10 Aug - 11 Aug
Best Western Kent Narrows Inn
Hyatt Place Kent Narrows & Marina
Relax by the fire pit in this scenic waterfront seating area, overlooking the marina with boats docked.

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (595)
"Great place to stay. "
The price is NZ$312
includes taxes & fees
29 July - 30 July
Hyatt Place Kent Narrows & Marina
Inn at Huntingfield Creek
Relax on the lakeside deck with a comfortable lounge chair, surrounded by lush greenery.

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (52)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
Inn at Huntingfield Creek
Mariners Motel
Docked in the marina, a sleek yacht awaits your arrival.

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is NZ$285
includes taxes & fees
11 Aug - 12 Aug
Mariners Motel
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
The price is NZ$442
includes taxes & fees
31 July - 1 Aug
Inn at Haven Harbour
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Welcome to Home 2 Suites by Milton, featuring a modern facade with a covered entrance and inviting lobby area.

Home2 Suites by Hilton Baltimore / Aberdeen, MD

3.0 star property
8.6 out of 10, Excellent, (313)
"All around good experience. The queen bed seemed small though. Looked like a full size."
The price is NZ$230
includes taxes & fees
24 Aug - 25 Aug
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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
Sign in
Sign up, it's free

Learn more about Chestertown

Quaint Chestertown awaits: its sports, university life, art and more!

See all hotels in Chestertown
Photo by Assya A
Open Photo by Assya A

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"This property is perfectly located within short walking distance of the USNA, downtown shopping/dining and the State House. It could not be in a better location. The property is historic, beautiful and well maintained. The room was spacious, clean and did not feel tired or in need of a refresh. We were absolutely thrilled with the property and will stay here every time we are back in town."
Darren 1-night trip
Posted 16 hours ago
Historic Inns of Annapolis

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 The Lodge at Great Oak Landing and Red Roof Inn & Suites Chestertown as top options for your stay. See all available top hotels, or vacation rentals in Chestertown.

What are some of the best holiday rentals that Chestertown has to offer?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Chestertown is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. 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 accommodation for a budget-friendly stay in Chestertown?

Based on reviews, Red Roof Inn & Suites Chestertown is a popular 2-star hotel for our travellers looking for an economical choice, and features free WiFi and free parking. Another top choice for your budget-friendly stay is Driftwood Inn. View all budget hotels 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's the best place to stay for couples in Chestertown?

Red Roof Inn & Suites Chestertown is a favourite hotel for couples, and features free WiFi and free parking. See all romantic hotels 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. The Lodge at Great Oak Landing and Red Roof Inn & Suites Chestertown 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's the best hotel in Chestertown to learn about local history?

Based on our travel expertise, Comfort Inn & Suites Chestertown is a top hotel on Expedia for those interested in history, and it features free breakfast and free WiFi. Also, notable landmarks to visit include Historical Society of Kent County Maryland. See more options for historical stays 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.

What is the best spa hotel in Chestertown?

Great Oak Manor is a top spa hotel featuring a private beach and a fitness centre. See all spa hotels 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.