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

Search Resort Hotels in Chestertown from CA $87

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Recommended hotels in Chestertown

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
7.8 out of 10, Good, (88 reviews)
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again "
United States
Nicola
The price is CA $187
CA $214 total
includes taxes & fees
Jun 29 - Jun 30
The Lodge at Great Oak Landing

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (926 reviews)
"Great visit"
United States
Danielle
The price is CA $159
CA $176 total
includes taxes & fees
Jul 16 - Jul 17
Comfort Inn & Suites Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (113 reviews)
"Every thing was great"
United States
lesia k.
The price is CA $140
CA $225 total
includes taxes & fees
Jul 6 - Jul 7
First Floor Studio Apartment in Historic Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (458 reviews)
"Perfect for an overnight trip, staff was very helpful."
United States
Anasmel
The price is CA $102
CA $113 total
includes taxes & fees
Jul 5 - Jul 6
Red Roof Inn & Suites Chestertown

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (177 reviews)
"Terrible !!! Dirty not clean the owner was rude and didn’t care about the conditions of the room. I asked for partial refund and was denied. Rat poop in the heaters. Dog hair in tubs dead bugs. Body fluids everywhere! Also drug dealers outside with guns. The owner still didn’t care what they were doing. Don’t go to this place it should be shut down !"
United States
Gabriel
The price is CA $90
CA $100 total
includes taxes & fees
Jun 24 - Jun 25
Driftwood Inn

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
9.8 out of 10, Exceptional, (29 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is CA $354
CA $545 total
includes taxes & fees
Jul 1 - Jul 2
Newly restored apartment in the heart of Chestertown

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, (1,003 reviews)
"Clean. Quiet, and nice breakfast"
United States
Mark
The price is CA $78
CA $87 total
includes taxes & fees
Jun 28 - Jun 29
Super 8 by Wyndham Havre De Grace Aberdeen Area

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (146 reviews)
"It was such a lovely quaint resort. I loved everything about staying there. Thank you."
United States
Sue
The price is CA $222
CA $294 total
includes taxes & fees
Jun 30 - Jul 1
Kent Island Resort

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,867 reviews)
"Great hotel..will definitely be back"
United States
Randy
The price is CA $128
CA $194 total
includes taxes & fees
Jul 1 - Jul 2
Historic Inns of Annapolis

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.8 out of 10, Good, (17 reviews)
"Nice place"
United States
christine
The price is CA $92
CA $127 total
includes taxes & fees
Jun 27 - Jun 28
Charming 2-bedroom house in Aberdeen with WiFi and AC

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (65 reviews)
"A beautiful place to spend a few days relaxing and enjoying nature. The owners are friendly, welcoming, and take excellent care of the property."
United States
Myrna
The price is CA $252
CA $280 total
includes taxes & fees
Jul 6 - Jul 7
Inn at Huntingfield Creek

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (925 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
The price is CA $142
CA $157 total
includes taxes & fees
Jul 6 - Jul 7
Quality Inn Grasonville near Kent Island

Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.8 out of 10, Exceptional, (96 reviews)
"Awesome place, great location"
United States
Mark M.
The price is CA $78
CA $317 total
includes taxes & fees
Jun 29 - Jun 30
Hidden Fells Point Gem / Private Courtyard Patio

Relax Inn Smyrna Dover Coastal Gateway

Relax Inn Smyrna Dover Coastal Gateway
2.0 star property
Smyrna
7.8 out of 10, Good, (104 reviews)
"Stuff"
United States
matt
The price is CA $140
CA $179 total
includes taxes & fees
Jun 25 - Jun 26
Relax Inn Smyrna Dover Coastal Gateway

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (555 reviews)
"The staff was wonderful! the place was nice and clean. everything was in walking distance. highly recommend staying here if visiting."
United States
Danielle
The price is CA $205
CA $229 total
includes taxes & fees
Jun 25 - Jun 26
Vandiver Inn

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (23 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is CA $96
CA $177 total
includes taxes & fees
Jun 29 - Jun 30
Guest Suite for up to 2 in a Victorian on the Chester River

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)
"Good hotel for the price"
United States
Brenda
The price is CA $155
CA $172 total
includes taxes & fees
Jul 6 - Jul 7
Best Western Kent Narrows 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, (611 reviews)
"Hotel was clean and staff were kind and friendly."
United States
Efua
The price is CA $125
CA $139 total
includes taxes & fees
Jun 29 - Jun 30
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is CA $184
CA $469 total
includes taxes & fees
Jun 30 - Jul 1
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Cozy Fells Point Gem / In The Heart of Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
Fells Point
9.8 out of 10, Exceptional, (206 reviews)
"Place worked great for our overnight stay"
United States
Adrienne K.
The price is CA $78
CA $315 total
includes taxes & fees
Jun 28 - Jun 29
Cozy Fells Point Gem / In The Heart of Fells Point
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

Find out more about Chestertown

Chestertown Resorts information

Number of reviews
12,868
Accommodation
0 Resorts
Lowest Price
CA $87
Highest Price
CA $294

Frequently asked questions

What is Chestertown like for a resort vacation?
Longing for a relaxing escape? Indulge in all the luxuries and comforts of a resort, where you can find everything you need for your stay from convenient food and drink options to entertainment and shopping. Browse the resorts in the area and discover the right one for you, whether you see yourself sitting down to fine dining or heading to the spa for a deep-tissue massage.
What can I do in Chestertown?
Check out the interesting exhibits at Historical Society of Kent County Maryland, or bring the kids to Crumpton Auction for some family fun. For more to see in the area, you can spend time at Chestertown Historic District or Rolphs Wharf Marina.
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.
What's the best way to get to and around Chestertown?
Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the city center. You can also search for flights into Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

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