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Find hotels in Chestertown, MD from SAR 200

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

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (379)
"Good location."
The price is SAR 285
SAR 316 total
includes taxes & fees
23 Jul - 24 Jul
Red Roof Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (785)
"It was a clean comfortable spot to rest for the night. "
The price is SAR 429
SAR 477 total
includes taxes & fees
17 Aug - 18 Aug
Comfort Inn & Suites Chestertown

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 SAR 491
SAR 545 total
includes taxes & fees
23 Jul - 24 Jul
The Lodge at Great Oak Landing

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 SAR 238
SAR 264 total
includes taxes & fees
23 Jul - 24 Jul
Driftwood Inn

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 SAR 375
SAR 416 total
includes taxes & fees
3 Aug - 4 Aug
Quality Inn

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (84)
"Owner was very nice. "
The price is SAR 300
SAR 334 total
includes taxes & fees
4 Aug - 5 Aug
Relax Inn Smyrna

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (817)
"Front desk service was exceptional!!"
The price is SAR 478
SAR 531 total
includes taxes & fees
19 Aug - 20 Aug
Hampton Inn Middletown

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (591)
"Easy to navigate and nice, helpful staff "
The price is SAR 435
SAR 483 total
includes taxes & fees
17 Aug - 18 Aug
Holiday Inn Express And Suites Middletown by IHG

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (255)
"Nice place to stay"
The price is SAR 394
SAR 437 total
includes taxes & fees
3 Aug - 4 Aug
Fairfield Inn & Suites by Marriott Middletown

Quality Inn

2.5 star property
7.8 out of 10, Good, (792)
"The place was clean and quiet, staff was great, not much nearby to see and do. It’s a fishing town. "
The price is SAR 369
SAR 410 total
includes taxes & fees
20 Aug - 21 Aug
Quality Inn

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

2.0 star property
6.8 out of 10, (925)
"This is a terrible place to stay. "
The price is SAR 204
SAR 229 total
includes taxes & fees
11 Aug - 12 Aug
Super 8 by Wyndham Havre De Grace Aberdeen Area

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (963)
"Great spot with beautiful views. "
The price is SAR 603
SAR 669 total
includes taxes & fees
28 Jul - 29 Jul
Hilton Garden Inn Kent Island Marina

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 SAR 521
SAR 579 total
includes taxes & fees
18 Aug - 19 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG

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 SAR 473
SAR 525 total
includes taxes & fees
10 Aug - 11 Aug
Best Western Kent Narrows Inn

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (593)
"Great place to stay. "
The price is SAR 571
SAR 633 total
includes taxes & fees
4 Aug - 5 Aug
Hyatt Place Kent Narrows & Marina

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

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 SAR 582
SAR 646 total
includes taxes & fees
10 Aug - 11 Aug
Mariners Motel

Inn at Haven Harbour

3.0 star property
The price is SAR 829
SAR 996 total
includes taxes & fees
31 Jul - 1 Aug
Inn at Haven Harbour

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 SAR 437
SAR 489 total
includes taxes & fees
10 Aug - 11 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.
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Stay near popular Chestertown attractions

Learn more about Chestertown

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

Somewhere over the rainbow... Terrific view on the plane back to the North.
Photo by Assya A
Open Photo by Assya A

Top Chestertown Hotel Reviews

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?

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 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 seasonal outdoor pool and a fitness center 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 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 Chestertown Historic District. 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.