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Recommended hotels in Chestertown

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 CA $175
CA $200 total
includes taxes & fees
May 13 - May 14
The Lodge at Great Oak Landing

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (111 reviews)
"Every thing was great"
United States
lesia k.
The price is CA $135
CA $217 total
includes taxes & fees
May 13 - May 14
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, (440 reviews)
"Nothing special but good for the price. "
United States
Andreas
The price is CA $98
CA $109 total
includes taxes & fees
May 31 - Jun 1
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 CA $161
CA $179 total
includes taxes & fees
May 31 - Jun 1
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 CA $87
CA $96 total
includes taxes & fees
May 13 - May 14
Driftwood Inn

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 CA $109
CA $140 total
includes taxes & fees
May 10 - May 11
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 CA $136
CA $151 total
includes taxes & fees
May 13 - May 14
Quality Inn Grasonville near Kent Island

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 CA $71
CA $80 total
includes taxes & fees
May 11 - May 12
Super 8 by Wyndham Havre De Grace Aberdeen Area

Adorable two-bedroom retreat close to Easton, Denton, Centreville

Adorable two-bedroom retreat close to Easton, Denton, Centreville
Queen Anne
10.0 out of 10, Exceptional, (28 reviews)
"Really cute little place - very clean and owners are great about checking in on you to make sure things are great."
United States
Cheryl
The price is CA $190
CA $412 total
includes taxes & fees
May 10 - May 11
Adorable two-bedroom retreat close to Easton, Denton, Centreville

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, (21 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is CA $93
CA $171 total
includes taxes & fees
May 14 - May 15
Guest Suite for up to 2 in a Victorian on the Chester River

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, (44 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is CA $235
CA $512 total
includes taxes & fees
May 14 - May 15
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 CA $217
CA $288 total
includes taxes & fees
May 10 - May 11
Kent Island Resort

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, (205 reviews)
"Amazing all around! Owner didn't miss a beat with communication, great location, cozy and quiet stay "
United States
Leanne
The price is CA $86
CA $319 total
includes taxes & fees
May 10 - May 11
Cozy Fells Point Gem / In The Heart of Fells Point

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is CA $261
CA $546 total
includes taxes & fees
Jun 9 - Jun 10
Charming Coastal/Country Home w/3 Acres & Sauna!

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 CA $157
CA $175 total
includes taxes & fees
May 27 - May 28
Best Western Kent Narrows Inn

Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.6 out of 10, Exceptional, (95 reviews)
"Awesome place, great location"
United States
Mark M.
The price is CA $94
CA $330 total
includes taxes & fees
May 25 - May 26
Hidden Fells Point Gem / Private Courtyard Patio

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 CA $116
CA $129 total
includes taxes & fees
May 25 - May 26
Quality Inn Smyrna

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (151 reviews)
"Great house for a quick little getaway with family. The house is perfect for families with children; relaxed and friendly, not fussy. Would definitely recommend."
United States
Alison R.
The price is CA $394
CA $772 total
includes taxes & fees
May 10 - May 11
5-bedroom vacation home 5 minutes from historic Charlestown

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (338 reviews)
"The staff was lovely and so accommodating. Definitely the best part of our stay."
United States
Maritza
The price is CA $150
CA $168 total
includes taxes & fees
May 17 - May 18
Fairfield Inn & Suites by Marriott Aberdeen

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 CA $120
CA $135 total
includes taxes & fees
May 13 - May 14
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
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
7,352
Accommodation
0 Resorts
Lowest Price
CA $80
Highest Price
CA $772

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 Rolphs Wharf Marina or Northern Chesapeake Bay.
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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