Photo by Assya A

Find hotels in Chestertown, MD from AED 219

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Compare 1,067 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (343)
"I stayed here one night and got a stripper pregnant. 10/10 will book again. "
The price is AED 251
AED 279 total
includes taxes & fees
22 Apr - 23 Apr
Red Roof Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (755)
"Check-in was quick & easy. The gentleman at the desk was wonderfully pleasant and very welcoming. Our room was clean and spacious. Beds were clean and comfortable. "
The price is AED 401
AED 445 total
includes taxes & fees
24 Apr - 25 Apr
Comfort Inn & Suites Chestertown

The Lodge at Great Oak Landing

3.5 star property
7.8 out of 10, Good, (47)
"Generally okay, Clean but property could use some upgrade"
The price is AED 397
AED 440 total
includes taxes & fees
27 Apr - 28 Apr
The Lodge at Great Oak Landing

Driftwood Inn

2.0 star property
5.2 out of 10, (169)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is AED 233
AED 259 total
includes taxes & fees
12 Apr - 13 Apr
Driftwood Inn

Quality Inn

2.5 star property
7.6 out of 10, Good, (995)
"Comfortable and clean"
The price is AED 331
AED 367 total
includes taxes & fees
13 Apr - 14 Apr
Quality Inn

Relax Inn Smyrna

2.0 star property
8.0 out of 10, Very Good, (75)
"The gentleman in the office was very nice & professional. The room could use some repair, especially the bathroom door. I was pleased with the comfortable bed and the full size shamoo, conditioner & shower gel dispensers in the shower. Loved the big towels too!"
The price is AED 327
AED 364 total
includes taxes & fees
13 Apr - 14 Apr
Relax Inn Smyrna

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (783)
"Wounderful"
The price is AED 446
AED 495 total
includes taxes & fees
20 Apr - 21 Apr
Hampton Inn Middletown

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (555)
"Beautiful hotel. Great service. I didn’t like that the suite was small and was not a separate room suite. The pool and fitness room was also too small."
The price is AED 459
AED 510 total
includes taxes & fees
20 Apr - 21 Apr
Holiday Inn Express And Suites Middletown by IHG

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (217)
"Never had a problem with Fairfield Inn. Very nicely done. Free breakfast if you want. Comfortable beds & clean rooms. "
The price is AED 404
AED 448 total
includes taxes & fees
5 May - 6 May
Fairfield Inn & Suites by Marriott Middletown

First Floor East Standard Deluxe

2.5 star property
The price is AED 1,288
AED 1,832 total
includes taxes & fees
13 Apr - 14 Apr
First Floor East Standard Deluxe

Top Floor Standard Deluxe

2.0 star property
The price is AED 1,288
AED 1,832 total
includes taxes & fees
13 Apr - 14 Apr
Top Floor Standard Deluxe

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 AED 1,288
AED 1,832 total
includes taxes & fees
13 Apr - 14 Apr
Top Floor Standard Deluxe

First Floor Standard Suite

2.0 star property
The price is AED 1,361
AED 1,910 total
includes taxes & fees
13 Apr - 14 Apr
First Floor Standard Suite

Second Floor Standard Deluxe

2.0 star property
The price is AED 1,288
AED 1,832 total
includes taxes & fees
13 Apr - 14 Apr
Second Floor Standard Deluxe

First Floor Standard Deluxe

2.0 star property
The price is AED 1,288
AED 1,832 total
includes taxes & fees
13 Apr - 14 Apr
First Floor Standard Deluxe

Top Floor Family Deluxe Bay View

2.5 star property
The price is AED 1,385
AED 1,935 total
includes taxes & fees
13 Apr - 14 Apr
Top Floor Family Deluxe Bay View

Top Floor East Family Deluxe

2.0 star property
The price is AED 1,288
AED 1,832 total
includes taxes & fees
13 Apr - 14 Apr
Top Floor East Family Deluxe

Top Floor Handicap Accessible Bay View

2.5 star property
The price is AED 1,385
AED 1,935 total
includes taxes & fees
13 Apr - 14 Apr
Top Floor Handicap Accessible Bay View

First Floor Standard Deluxe King

2.5 star property
The price is AED 1,288
AED 1,832 total
includes taxes & fees
13 Apr - 14 Apr
First Floor Standard Deluxe King

First Floor East Family Deluxe

2.5 star property
The price is AED 1,288
AED 1,832 total
includes taxes & fees
13 Apr - 14 Apr
First Floor East Family 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.
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 Red Roof Inn & Suites Chestertown and Driftwood Inn 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?

Red Roof Inn & Suites Chestertown is a top LGBTQ-friendly hotel that features free WiFi and free parking. Comfort Inn & Suites Chestertown and The Lodge at Great Oak Landing 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 41 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 Crumpton Auction. 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.