Find hotels in Chestertown, MD from 1.540.723 ₫

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Our top choices for Chestertown hotels

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (80 reviews)
"clean, comfortable, and staff was friendly and helpful. "
United States
Gail
The price is 3.480.548 ₫
3.979.310 ₫ total
includes taxes & fees
10 May - 11 May
The Lodge at Great Oak Landing

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (440 reviews)
"Nothing special but good for the price. "
United States
Andreas
The price is 1.893.939 ₫
2.102.273 ₫ total
includes taxes & fees
14 May - 15 May
Red Roof Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (909 reviews)
"Great visit"
United States
Danielle
The price is 2.998.531 ₫
3.328.370 ₫ total
includes taxes & fees
25 May - 26 May
Comfort Inn & Suites Chestertown

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (175 reviews)
"Rooms are clean, staf was helpful "
United States
Daryl
The price is 1.670.558 ₫
1.854.451 ₫ total
includes taxes & fees
9 May - 10 May
Driftwood Inn

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is 4.077.740 ₫
4.526.292 ₫ total
includes taxes & fees
12 May - 13 May
Haven Point Inn and Gallery

Relax Inn Smyrna Dover Coastal Gateway

Relax Inn Smyrna Dover Coastal Gateway
2.0 star property
Smyrna
7.8 out of 10, Good, (96 reviews)
"I was in town for just one night and ended up booking this last minute. I’ve never stayed at a motel before because of the stigma, but I was pleasantly surprised. Everything was very clean, and the owner at the front desk was extremely friendly and welcoming. A nice bonus was the smart TV, which let me log into my own accounts and relax. Overall, a great experience and definitely changed my perspective on motels."
United States
Michael
The price is 2.209.872 ₫
2.828.636 ₫ total
includes taxes & fees
10 May - 11 May
Relax Inn Smyrna Dover Coastal Gateway

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (903 reviews)
"Breakfast menu had a great variety and was fresh. "
United States
Timothy
The price is 2.461.218 ₫
2.731.952 ₫ total
includes taxes & fees
14 May - 15 May
Quality Inn Grasonville near Kent Island

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
2.0 star property
North East
8.8 out of 10, Excellent, (3 reviews)
"Very nice cabin. By the town and easy drive to everything. "
United States
Mark
The price is 9.202.998 ₫
11.149.502 ₫ total
includes taxes & fees
14 May - 15 May
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
"Very nice room and wonderful stay."
United States
Julie
The price is 4.709.132 ₫
6.134.105 ₫ total
includes taxes & fees
12 May - 13 May
Kent Island Resort

Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.6 out of 10, (987 reviews)
"Cleaning lady and front desk were very frindly, helpful, speedy & great at there job."
United States
Mary
The price is 1.375.645 ₫
1.540.723 ₫ total
includes taxes & fees
12 May - 13 May
Super 8 by Wyndham Havre De Grace Aberdeen Area

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (642 reviews)
"Very good breakfast. Nice selection to choose from. "
United States
Charlotte
The price is 2.480.844 ₫
2.778.546 ₫ total
includes taxes & fees
26 May - 27 May
Hampton Inn & Suites Baltimore/Aberdeen

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,004 reviews)
"Not unique but friendly staff Excellent breakfast Clean"
United States
Kevin
The price is 3.027.525 ₫
3.360.553 ₫ total
includes taxes & fees
27 May - 28 May
Best Western Kent Narrows Inn

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (543 reviews)
"Breakfast menu was very good, staff friendly and helpful. "
United States
JoEllen
The price is 3.803.976 ₫
4.260.454 ₫ total
includes taxes & fees
14 May - 15 May
Vandiver Inn

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (591 reviews)
"Great place to stay. "
United States
Nathan
The price is 2.315.104 ₫
2.592.916 ₫ total
includes taxes & fees
11 May - 12 May
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1,003 reviews)
"Great place to stay"
United States
Harry
The price is 2.325.627 ₫
2.604.703 ₫ total
includes taxes & fees
27 May - 28 May
La Quinta Inn & Suites by Wyndham Aberdeen-APG

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
United States
Sandra
The price is 4.746.752 ₫
5.268.966 ₫ total
includes taxes & fees
10 May - 11 May
Inn at Huntingfield Creek

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,002 reviews)
"My visit at the Hotel was amazing & peaceful."
United States
Milton
The price is 2.401.920 ₫
2.666.052 ₫ total
includes taxes & fees
26 May - 27 May
Quality Inn Smyrna

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (380 reviews)
"Really nice hotel."
United States
Gerard
The price is 2.841.264 ₫
3.153.803 ₫ total
includes taxes & fees
25 May - 26 May
Fairfield Inn & Suites by Marriott Middletown

Motel Edgewood

Motel Edgewood
2.0 star property
Edgewood
7.6 out of 10, Good, (13 reviews)
"Bed was clean and crisply made. Occupants were respectful of sleeping hours. Check-in and check-out were simple. Parking was convenient and had easy access to the highway."
United States
Nancy
The price is 1.420.369 ₫
1.590.845 ₫ total
includes taxes & fees
14 May - 15 May
Motel Edgewood

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,008 reviews)
"Best place to stay"
United States
Victor
The price is 2.325.627 ₫
2.604.701 ₫ total
includes taxes & fees
25 May - 26 May
Hampton Inn & Suites Edgewood/Aberdeen-South
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

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Top Chestertown Hotel Reviews

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Hotels in Chestertown with star rating

Frequently asked questions

What's the seasonal weather like in Chestertown?
The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.