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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, (77 reviews)
"Very nice rooms, "
United States
Stephania
The price is ₩159,277
₩182,092 total
includes taxes & fees
Apr 14 - Apr 15
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, (434 reviews)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
The price is ₩106,185
₩117,865 total
includes taxes & fees
May 6 - May 7
Red Roof Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (896 reviews)
"Best place to stay always "
United States
Robert
The price is ₩183,184
₩203,334 total
includes taxes & fees
May 3 - May 4
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
Driftwood Inn

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is ₩228,592
₩253,737 total
includes taxes & fees
Apr 21 - Apr 22
Haven Point Inn and Gallery

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (135 reviews)
"Beautiful hotel, nice staff"
United States
Kim
The price is ₩164,287
₩226,603 total
includes taxes & fees
Apr 13 - Apr 14
Kent Island Resort

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (93 reviews)
"The room was over the garage. You couldn’t stand up in half the room as the ceiling was too low. Multiple tripping areas walking into and out of the space. No heat in bathroom. You have to walk to the front of house to enter for coffee in the morning. They have the nerve to charge you to park at the house. "
United States
Richard
The price is ₩267,807
₩305,311 total
includes taxes & fees
Apr 14 - Apr 15
Flag House Inn

Relax Inn Smyrna

Relax Inn Smyrna
2.0 star property
Smyrna
8.0 out of 10, Very Good, (94 reviews)
"Great location"
United States
Patrick
The price is ₩146,004
₩162,414 total
includes taxes & fees
Apr 15 - Apr 16
Relax Inn Smyrna

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,000 reviews)
"My visit at the Hotel was amazing & peaceful."
United States
Milton
The price is ₩114,016
₩126,558 total
includes taxes & fees
May 10 - May 11
Quality Inn Smyrna

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (538 reviews)
"As always we loved our stay! Definitely will be coming back "
United States
John
The price is ₩197,770
₩221,502 total
includes taxes & fees
Apr 12 - Apr 13
Vandiver Inn

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (62 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 ₩206,633
₩229,374 total
includes taxes & fees
Apr 12 - Apr 13
Inn at Huntingfield Creek

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, (1,008 reviews)
"Near $95 and good place to stay"
United States
Thandavarayan
The price is ₩130,371
₩146,015 total
includes taxes & fees
May 5 - May 6
La Quinta Inn & Suites by Wyndham Aberdeen-APG

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,001 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is ₩146,794
₩162,941 total
includes taxes & fees
Apr 21 - Apr 22
Best Western Kent Narrows Inn

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (368 reviews)
"Clean room, felt very safe and secure, free parking, staff very friendly, plenty of eating and shopping close by"
United States
Taneica
The price is ₩153,378
₩170,250 total
includes taxes & fees
May 10 - May 11
Fairfield Inn & Suites by Marriott Middletown

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (674 reviews)
"Great location and nice place to stay. Walk to nearby things to do and enjoy. "
United States
Sharon
The price is ₩148,954
₩165,339 total
includes taxes & fees
Apr 26 - Apr 27
Holiday Inn Express & Suites Middletown by IHG

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, (980 reviews)
"Cleaning lady and front desk were very frindly, helpful, speedy & great at there job."
United States
Mary
The price is ₩75,893
₩85,001 total
includes taxes & fees
Apr 14 - Apr 15
Super 8 by Wyndham Havre De Grace Aberdeen Area

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
9.8 out of 10, Exceptional, (34 reviews)
"Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff"
United States
Ian
The price is ₩272,921
₩311,131 total
includes taxes & fees
Apr 12 - Apr 13
134 Prince - Luxury Boutique Hotel

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (362 reviews)
"Staff was very friendly and it was a perfect location for us"
United States
Ryan
The price is ₩149,957
₩167,953 total
includes taxes & fees
Apr 16 - Apr 17
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (888 reviews)
"Staff was nice and room was clean "
United States
Lauren
The price is ₩144,146
₩160,002 total
includes taxes & fees
Apr 13 - Apr 14
Quality Inn Grasonville near Kent Island

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,002 reviews)
"Beautiful area"
United States
Dan
The price is ₩192,283
₩213,434 total
includes taxes & fees
Apr 28 - Apr 29
Hilton Garden Inn Kent Island Marina
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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Top Chestertown Hotel Reviews