Photo by Assya A

Find hotels in Chestertown, MD from AED 204

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Compare 1,055 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, (749)
"The hotel was spotless. Very clean. Comfortable and safe. "
The price is AED 381
AED 423 total
includes taxes & fees
20 Apr - 21 Apr
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (338)
"I loved the decor of my room. The king size bed was cozy. "
The price is AED 228
AED 253 total
includes taxes & fees
31 Mar - 1 Apr
Red Roof Inn & Suites Chestertown

The Lodge at Great Oak Landing

3.5 star property
7.8 out of 10, Good, (46)
"Generally okay, Clean but property could use some upgrade"
The price is AED 397
AED 440 total
includes taxes & fees
13 Apr - 14 Apr
The Lodge at Great Oak Landing

Driftwood Inn

2.0 star property
5.0 out of 10, (168)
"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
31 Mar - 1 Apr
Driftwood Inn

Quality Inn

2.5 star property
7.6 out of 10, Good, (991)
"It was clean and actually smelled good. It was comfortable. They may need more TV channels. But everything was good."
The price is AED 331
AED 367 total
includes taxes & fees
31 Mar - 1 Apr
Quality Inn

Relax Inn Smyrna

2.0 star property
8.0 out of 10, Very Good, (74)
"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
31 Mar - 1 Apr
Relax Inn Smyrna

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (781)
"Wounderful"
The price is AED 387
AED 430 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, (550)
"Great"
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, (210)
"Clean new property"
The price is AED 386
AED 428 total
includes taxes & fees
7 Apr - 8 Apr
Fairfield Inn & Suites by Marriott Middletown

Spectacular Top Floor Deluxe Suite With Beautiful View & More!

2.5 star property
The price is AED 1,385
AED 1,935 total
includes taxes & fees
9 Apr - 10 Apr
Spectacular Top Floor Deluxe Suite With Beautiful View & More!

First Floor Master Suite Bay View

2.0 star property
The price is AED 1,652
AED 2,219 total
includes taxes & fees
9 Apr - 10 Apr
First Floor Master Suite Bay View

Second Floor East Standard Suite

2.0 star property
The price is AED 1,361
AED 1,910 total
includes taxes & fees
9 Apr - 10 Apr
Second Floor East Standard Suite

Top Floor East Family Deluxe

2.0 star property
The price is AED 1,288
AED 1,832 total
includes taxes & fees
9 Apr - 10 Apr
Top Floor East Family Deluxe

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

First Floor Standard Deluxe Bay View

2.5 star property
The price is AED 1,385
AED 1,935 total
includes taxes & fees
9 Apr - 10 Apr
First Floor Standard Deluxe Bay View

First Floor East Standard Deluxe

2.5 star property
The price is AED 1,288
AED 1,832 total
includes taxes & fees
9 Apr - 10 Apr
First Floor East 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
9 Apr - 10 Apr
Top Floor Standard Deluxe

Second Floor Master Suite Bay View

3.5 star property
The price is AED 1,652
AED 2,219 total
includes taxes & fees
9 Apr - 10 Apr
Second Floor Master Suite Bay View

Top Floor Handicap Accessible Bay View

2.5 star property
The price is AED 1,385
AED 1,935 total
includes taxes & fees
9 Apr - 10 Apr
Top Floor Handicap Accessible Bay View

Second Conference Standard Suite Bay View

2.0 star property
The price is AED 1,458
AED 2,013 total
includes taxes & fees
9 Apr - 10 Apr
Second Conference Standard Suite 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.
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Learn more about Chestertown

Quaint Chestertown awaits: its sports, university life, wildlife, 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?

240' Private Beachfront @Kent Island Love Point - Great for Large Groups: This vacation home rental outside of Chestertown is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 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?

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 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 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.