An aerial view of a town with a river, buildings, and surrounding greenery.

Best Resorts in Chestertown

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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, (89 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
$151 nightly
The price is $168
Jul 5 - Jul 6
Total with taxes and fees
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, (458 reviews)
"Perfect for an overnight trip, staff was very helpful."
United States
Anasmel
$72 nightly
The price is $80
Jul 12 - Jul 13
Total with taxes and fees
Red Roof Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (929 reviews)
"Great visit"
United States
Danielle
$103 nightly
The price is $115
Jul 26 - Jul 27
Total with taxes and fees
Comfort 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
$64 nightly
The price is $70
Jul 4 - Jul 5
Total with taxes and fees
Driftwood Inn

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (115 reviews)
"Every thing was great"
United States
lesia k.
$144 nightly
The price is $159
Jul 6 - Jul 7
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown

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 traveler
$349 nightly
The price is $385
Jul 9 - Jul 10
Total with taxes and fees
Newly restored apartment in the heart of Chestertown

Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"The house was lovely, very comfortable and hosts were very responsive! We will be back for another stay. "
United States
Diana S.
$423 nightly
The price is $440
Jul 6 - Jul 7
Total with taxes and fees
Wren Retweet- Country Estate in Center of C’Town

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (150 reviews)
"It was such a lovely quaint resort. I loved everything about staying there. Thank you."
United States
Sue
$179 nightly
The price is $195
Jul 5 - Jul 6
Total with taxes and fees
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, (1,001 reviews)
"Clean. Quiet, and nice breakfast"
United States
Mark
$51 nightly
The price is $58
Jul 6 - Jul 7
Total with taxes and fees
Super 8 by Wyndham Havre De Grace Aberdeen Area

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (558 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
$161 nightly
The price is $180
Jul 6 - Jul 7
Total with taxes and fees
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.
$118 nightly
The price is $125
Jul 6 - Jul 7
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River

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
$88 nightly
The price is $93
Jul 6 - Jul 7
Total with taxes and fees
Charming 2-bedroom house in Aberdeen with WiFi and AC

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (928 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
$100 nightly
The price is $111
Jul 12 - Jul 13
Total with taxes and fees
Quality Inn Grasonville near Kent Island

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, (47 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
$278 nightly
The price is $300
Jul 6 - Jul 7
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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
$178 nightly
The price is $198
Jul 6 - Jul 7
Total with taxes and fees
Inn at Huntingfield Creek

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1,006 reviews)
"We had a very nice stay."
United States
Aimee
$95 nightly
The price is $106
Jul 5 - Jul 6
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

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
$130 nightly
The price is $148
Jul 12 - Jul 13
Total with taxes and fees
Historic Inns of Annapolis

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
$95 nightly
The price is $101
Jul 5 - Jul 6
Total with taxes and fees
Relax Inn Smyrna Dover Coastal Gateway

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,003 reviews)
"Good hotel for the price"
United States
Brenda
$125 nightly
The price is $139
Jul 5 - Jul 6
Total with taxes and fees
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, (612 reviews)
"Hotel was clean and staff were kind and friendly."
United States
Efua
$100 nightly
The price is $112
Aug 3 - Aug 4
Total with taxes and fees
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
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Top Chestertown Hotel Reviews

Find out more about Chestertown

Chestertown Resorts information

Number of reviews
9,136
Accommodation
0 Resorts
Lowest Price
$58
Highest Price
$440

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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