Photo by Assya A

Find hotels in Chestertown, MD from SAR 223

    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
9 Jum. I - 10 Jum. I
Tomorrow
10 Jum. I - 11 Jum. I
This weekend
9 Jum. I - 11 Jum. I
Next weekend
16 Jum. I - 18 Jum. I

Filter by

Guest rating
Guest rating
Star rating

Compare 1,075 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (761)
"Staff was efficient and very helpful. Clean room with microwave & fridge - well stocked linens in bathroom - great breakfast - thank you for a comfortable stay."
The price is SAR 411
SAR 457 total
includes taxes & fees
18 May - 19 May
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (350)
"Easy to get to, food all around!"
The price is SAR 257
SAR 285 total
includes taxes & fees
18 May - 19 May
Red Roof Inn & Suites Chestertown
The Lodge at Great Oak Landing
Private beach nearby, sun loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
7.8 out of 10, Good, (48)
"Wonderful quiet place. Enjoyed our night."
The price is SAR 441
SAR 490 total
includes taxes & fees
11 May - 12 May
The Lodge at Great Oak Landing
Driftwood Inn
Lobby

Driftwood Inn

2.0 star property
5.2 out of 10, (170)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is SAR 238
SAR 264 total
includes taxes & fees
20 May - 21 May
Driftwood Inn
Quality Inn
Property amenity

Quality Inn

2.5 star property
7.6 out of 10, Good, (1002)
"Clean and convenient to Bombay Hook"
The price is SAR 346
SAR 384 total
includes taxes & fees
13 May - 14 May
Quality Inn
Relax Inn Smyrna
Deluxe Double or Twin Room | Premium bedding, down comforters, individually furnished, desk

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (77)
"Overall experience was good. Convenient clean and efficient for the price. Definitely on the cleaner side compared to other motels. Shops and convenience stores are within walking distance. The walls are quite thin and the motel is directly next to a main road so if you are sensitive to sound or have kids, be aware... Even though I stayed in a room furthest from the road, the sound of traffic still carried in pretty loud."
The price is SAR 334
SAR 371 total
includes taxes & fees
11 May - 12 May
Relax Inn Smyrna
Hampton Inn Middletown
Indoor pool

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (790)
"Would definitely stay again"
The price is SAR 418
SAR 464 total
includes taxes & fees
27 May - 28 May
Hampton Inn Middletown
Holiday Inn Express And Suites Middletown by IHG
Exterior

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (563)
"Nice hotel a little far off the route, but worth it."
The price is SAR 503
SAR 558 total
includes taxes & fees
2 Jun - 3 Jun
Holiday Inn Express And Suites Middletown by IHG
Fairfield Inn & Suites by Marriott Middletown
Lobby

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (225)
"The staff was very professional and helpful. Great location. "
The price is SAR 431
SAR 479 total
includes taxes & fees
2 Jun - 3 Jun
Fairfield Inn & Suites by Marriott Middletown
Top Floor Standard Deluxe
Miscellaneous

Top Floor Standard Deluxe

2.5 star property
10.0 out of 10, Exceptional, (1)
"Very relaxing and peaceful love it can’t wait to be there again….."
The price is SAR 1,259
SAR 1,811 total
includes taxes & fees
11 May - 12 May
Top Floor Standard Deluxe
Top Floor Family Deluxe Bay View
Miscellaneous

Top Floor Family Deluxe Bay View

2.5 star property
The price is SAR 1,354
SAR 1,912 total
includes taxes & fees
21 May - 22 May
Top Floor Family Deluxe Bay View
Second Conference Family Deluxe Bay View
Miscellaneous

Second Conference Family Deluxe Bay View

2.5 star property
The price is SAR 1,354
SAR 1,912 total
includes taxes & fees
23 May - 24 May
Second Conference Family Deluxe Bay View
First Floor Standard Suite
Miscellaneous

First Floor Standard Suite

2.0 star property
The price is SAR 1,330
SAR 1,887 total
includes taxes & fees
21 May - 22 May
First Floor Standard Suite
Top Floor Standard Deluxe
Miscellaneous

Top Floor Standard Deluxe

2.0 star property
The price is SAR 1,259
SAR 1,811 total
includes taxes & fees
11 May - 12 May
Top Floor Standard Deluxe
First Floor Standard Deluxe
Miscellaneous

First Floor Standard Deluxe

2.0 star property
The price is SAR 1,259
SAR 1,811 total
includes taxes & fees
11 May - 12 May
First Floor Standard Deluxe
First Floor Standard Deluxe King
Miscellaneous

First Floor Standard Deluxe King

2.5 star property
The price is SAR 1,259
SAR 1,811 total
includes taxes & fees
11 May - 12 May
First Floor Standard Deluxe King
Second Floor Standard Deluxe
Miscellaneous

Second Floor Standard Deluxe

2.0 star property
The price is SAR 1,259
SAR 1,811 total
includes taxes & fees
11 May - 12 May
Second Floor Standard Deluxe
First Floor Master Suite Bay View
Miscellaneous

First Floor Master Suite Bay View

2.0 star property
First Floor Master Suite Bay View
First Floor East Standard Deluxe
Miscellaneous

First Floor East Standard Deluxe

2.5 star property
The price is SAR 1,259
SAR 1,811 total
includes taxes & fees
13 May - 14 May
First Floor East Standard Deluxe
Top Floor Handicap Accessible Bay View
Miscellaneous

Top Floor Handicap Accessible Bay View

2.5 star property
The price is SAR 1,354
SAR 1,912 total
includes taxes & fees
23 May - 24 May
Top Floor Handicap Accessible Bay View
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.
Don't see what you're looking for?
See all available properties in Chestertown
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
Somewhere over the rainbow... Terrific view on the plane back to the North.
Photo by Assya A
Open Photo by Assya A

Frequently asked questions

Where is the best place for a stay in Chestertown?

Comfort Inn & Suites Chestertown is a favorite 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 trip. See all available top hotels, or vacation rentals in Chestertown.

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

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This vacation home rental outside of Chestertown is located in the city center and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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, most hotel bookings are fully refundable as long as you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, 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.

Where can I learn more about changing or cancelling my trip to Chestertown?

For more details about rescheduling or cancelling your trip to Chestertown, click here.

What's the best hotel for families 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 kid-friendly vacation. Kids of all ages will also enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.

What's the best LGBTQ-friendly accommodation in Chestertown?

The Lodge at Great Oak Landing is a top LGBTQ-friendly lodge, and features a golf course and free WiFi. Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown are other good options for your trip.

What's the best pet-friendly hotel in Chestertown?

Comfort Inn & Suites Chestertown is a top hotel for people traveling with their pets, and offers a fitness center and laundry facilities for its human guests. Other good options to stay with your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn. See more pet-friendly hotel accommodations in Chestertown.

Where is the best hotel to stay near Washington College?

Adjacent to Washington College, Driftwood Inn is one of the top choices for your stay based on our traveler data, and this property offers free parking and free WiFi. Other good options close by include Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown.

What about the best place to stay near Rolphs Wharf Marina?

One of the top choices for your stay is Comfort Inn & Suites Chestertown, located 4.1 mi (6.6 km) from Rolphs Wharf Marina, and this hotel offers free breakfast and free parking. Driftwood Inn and Red Roof Inn & Suites Chestertown are two other good options within a few miles.

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 accommodations with pools in Chestertown?

The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool, 3 bars, and free WiFi. View all hotels with pools in Chestertown.

What's the best hotel for staying near Salisbury - Ocean City Wicomico Regional Airport (SBY)?

Country Inn & Suites by Radisson, Salisbury, MD is one of the top choices for your stay and is a popular 3-star hotel featuring free breakfast and an indoor pool. It's located 2.2 mi (3.6 km) from Salisbury - Ocean City Wicomico Regional Airport. Other options close to the airport include Microtel Inn & Suites by Wyndham Salisbury and Sleep Inn Salisbury.

How is it to stay in Chestertown?

Visitors to Chestertown are sure to enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals, and art. In Chestertown, there are 43 hotels and other accommodations to choose from. Find out more about Chestertown.

What are the top places to visit 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 agenda are Rolphs Wharf Marina and Sumner Hall. Check out what more 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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.