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Find hotels in Chestertown, MD from SAR 208

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Compare 1,079 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (759)
"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 456 total
includes taxes & fees
18 May - 19 May
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (349)
"Easy to get to, food all around!"
The price is SAR 257
SAR 285 total
includes taxes & fees
12 May - 13 May
Red Roof Inn & Suites Chestertown

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

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
14 May - 15 May
Driftwood Inn

Quality Inn

2.5 star property
7.6 out of 10, Good, (1003)
"Great price and clean hotel! Very impressed "
The price is SAR 344
SAR 382 total
includes taxes & fees
25 May - 26 May
Quality Inn

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
6 May - 7 May
Relax Inn Smyrna

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (788)
"Would definitely stay again"
The price is SAR 415
SAR 460 total
includes taxes & fees
27 May - 28 May
Hampton Inn Middletown

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (560)
"Nice hotel a little far off the route, but worth it."
The price is SAR 503
SAR 558 total
includes taxes & fees
18 May - 19 May
Holiday Inn Express And Suites Middletown by IHG

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (223)
"Ease of check-in and quiet 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

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 1,258
SAR 1,811 total
includes taxes & fees
11 May - 12 May
Top Floor Standard Deluxe

First Floor Master Suite Bay View

2.0 star property
The price is SAR 1,615
SAR 2,189 total
includes taxes & fees
11 May - 12 May
First Floor Master Suite Bay View

Second Floor Master Suite Bay View

3.5 star property
The price is SAR 1,615
SAR 2,189 total
includes taxes & fees
22 May - 23 May
Second Floor Master Suite Bay View

Top Floor Handicap Accessible Bay View

2.5 star property
The price is SAR 1,353
SAR 1,912 total
includes taxes & fees
11 May - 12 May
Top Floor Handicap Accessible Bay View

Top Floor Standard Suite Bay View

2.5 star property
The price is SAR 1,425
SAR 1,987 total
includes taxes & fees
11 May - 12 May
Top Floor Standard Suite Bay View

Top Floor Standard Deluxe

2.0 star property
The price is SAR 1,258
SAR 1,811 total
includes taxes & fees
6 May - 7 May
Top Floor Standard Deluxe

Fantastic Suite With King Bed and Beautiful Bay View!

2.0 star property
The price is SAR 1,353
SAR 1,912 total
includes taxes & fees
11 May - 12 May
Fantastic Suite With King Bed and Beautiful Bay View!

Top Floor Family Deluxe Bay View

2.5 star property
The price is SAR 1,353
SAR 1,912 total
includes taxes & fees
11 May - 12 May
Top Floor Family Deluxe Bay View

First Floor East Standard Deluxe

2.5 star property
The price is SAR 1,258
SAR 1,811 total
includes taxes & fees
11 May - 12 May
First Floor East Standard Deluxe

Second Conference Family Deluxe Bay View

2.5 star property
The price is SAR 1,353
SAR 1,912 total
includes taxes & fees
11 May - 12 May
Second Conference Family Deluxe Bay View

Second Floor Standard Deluxe

2.0 star property
The price is SAR 1,258
SAR 1,811 total
includes taxes & fees
11 May - 12 May
Second Floor Standard Deluxe
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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Learn more about Chestertown

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

Somewhere over the rainbow... Terrific view on the plane back to the North.
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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?

Red Roof Inn & Suites Chestertown is a hotel with free parking and laundry facilities, and it's a top choice on Expedia for families. Comfort 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. Red Roof Inn & Suites Chestertown and Comfort Inn & Suites Chestertown are other good options for your trip.

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

Red Roof Inn & Suites Chestertown is a top hotel for people traveling with their pets, and offers laundry facilities and free newspapers for its human guests. Other good options to stay with your pet include Comfort 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 44 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 Urieville Park. 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.