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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
8.0 out of 10, Very good, (81 reviews)
"clean, comfortable, and staff was friendly and helpful. "
United States
Gail
The price is CA $181
CA $207 total
includes taxes & fees
May 17 - May 18
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 CA $99
CA $110 total
includes taxes & fees
May 24 - May 25
Red Roof Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (911 reviews)
"Great visit"
United States
Danielle
The price is CA $149
CA $165 total
includes taxes & fees
Jun 7 - Jun 8
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, (111 reviews)
"Every thing was great"
United States
lesia k.
The price is CA $136
CA $218 total
includes taxes & fees
May 18 - May 19
First Floor Studio Apartment in Historic Chestertown

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (176 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 $87
CA $97 total
includes taxes & fees
May 19 - May 20
Driftwood Inn

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 $204
CA $272 total
includes taxes & fees
May 26 - May 27
Kent Island Resort

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (906 reviews)
"Breakfast menu had a great variety and was fresh. "
United States
Timothy
The price is CA $140
CA $156 total
includes taxes & fees
May 19 - May 20
Quality Inn Grasonville near Kent Island

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,002 reviews)
"It is a nice Hotel."
United States
Dale
The price is CA $158
CA $175 total
includes taxes & fees
May 27 - May 28
Best Western Kent Narrows 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, (21 reviews)
"Good place, clean and a good location."
United States
Bernard S.
The price is CA $93
CA $172 total
includes taxes & fees
May 21 - May 22
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)
"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 $114
CA $368 total
includes taxes & fees
May 17 - May 18
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (8 reviews)
"It is a warm and welcoming little home away from home. We will be back!"
United States
Brittany C.
The price is CA $203
CA $288 total
includes taxes & fees
May 18 - May 19
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

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 $238
CA $520 total
includes taxes & fees
May 27 - May 28
Charming Coastal/Country Home w/3 Acres & Sauna!

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 $118
CA $152 total
includes taxes & fees
May 18 - May 19
Relax Inn Smyrna Dover Coastal Gateway

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (21 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is CA $169
CA $402 total
includes taxes & fees
May 17 - May 18
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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 $76
CA $308 total
includes taxes & fees
May 19 - May 20
Hidden Fells Point Gem / Private Courtyard Patio

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (648 reviews)
"Clean, comfortable, decent breakfast."
United States
Diane
The price is CA $130
CA $145 total
includes taxes & fees
May 25 - May 26
Hampton Inn & Suites Baltimore/Aberdeen

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,001 reviews)
"The rooms were clean and the staff was very kind and helpful. Overall, it was a great value for us!"
United States
Jesse
The price is CA $123
CA $136 total
includes taxes & fees
Jun 16 - Jun 17
Quality Inn Smyrna

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 $78
CA $309 total
includes taxes & fees
May 27 - May 28
Cozy Fells Point Gem / In The Heart of Fells Point

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, (375 reviews)
"Great stay at this"
United States
Wilson
The price is CA $134
CA $150 total
includes taxes & fees
May 25 - May 26
Home2 Suites by Hilton Baltimore / Aberdeen, MD

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 CA $209
CA $234 total
includes taxes & fees
May 17 - May 18
Vandiver Inn
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 Villas information

Number of reviews
6,775
Accommodation
4 Villas
Lowest Price
CA $97
Highest Price
CA $520

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What is there to do near my villa in Chestertown?
If you want to discover the sights of Chestertown, make your way to Rolphs Wharf Marina. It's a winner with travelers and locals alike.

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