A coastal town with a marina, a bridge, and a highway.

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Our top choices for Kent County hotels

1. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (129 reviews)
"Nice restairant and bar"
United States
Steve allen
$124 nightly
The price is $137
Nov 10 - Nov 11
Total with taxes and fees
The Lodge at Great Oak Landing

2. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (1,000 reviews)
"The front desk staff were so nice, room very clean."
United States
John
$97 nightly
The price is $107
Dec 6 - Dec 7
Total with taxes and fees
Comfort Inn & Suites Chestertown

3. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (513 reviews)
"Nice clean place and priced good. Plenty of mirrors, plenty of counter space, many tv channels even Christian based ones and comfortable bed. The room needs up dating since damage area on ceiling and corner location rug worn spot. I felt safe as a solo, could check in late and close to historic Chestertown. I would come again."
United States
Regina
$72 nightly
The price is $80
Nov 16 - Nov 17
Total with taxes and fees
Red Roof Inn & Suites Chestertown

4. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (74 reviews)
"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us. The breakfast was also absolutely delicious. Definitely would recommend this I"
United States
Christine
$156 nightly
The price is $173
Nov 16 - Nov 17
Total with taxes and fees
Inn at Huntingfield Creek

5. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.4 out of 10, (183 reviews)
"It was a nice, clean place to stay the night."
United States
Kathy
$64 nightly
The price is $70
Nov 10 - Nov 11
Total with taxes and fees
Driftwood Inn

6. Inn at Haven Harbour

Inn at Haven Harbour
3.0 star property
Rock Hall
7.8 out of 10, Good, (6 reviews)
"Friendly staff at check in. This lady was helpful thru entire stay. Her name is Sharon. The Harbor had a Luau on Saturday which we attended since our son is a slip holder. Great weekend. "
United States
Gloria
Inn at Haven Harbour

7. Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
9.6 out of 10, Exceptional, (20 reviews)
"We enjoyed our stay and would go back again."
United States
Linda
Haven Point Inn and Gallery

8. 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, (32 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
$102 nightly
The price is $108
Nov 10 - Nov 11
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River

9. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
$264 nightly
The price is $292
Nov 10 - Nov 11
Total with taxes and fees
BAYSIDE BUNGALOW

10. 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, (33 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$256 nightly
The price is $283
Nov 12 - Nov 13
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

11. Life is better at the RIVER!--Cozy waterfront cottage

Life is better at the RIVER!--Cozy waterfront cottage
Galena
10.0 out of 10, Exceptional, (123 reviews)
"Absolutely perfect place to retreat. The house are genuinely loving, and it shows in every detail about the cottage."
United States
Katie S.
Life is better at the RIVER!--Cozy waterfront cottage

12. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$133 nightly
The price is $147
Nov 10 - Nov 11
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown

13. Serene Waterfront Cottage with dock and gorgeous views.

Serene Waterfront Cottage with dock and gorgeous views.
Rock Hall
9.6 out of 10, Exceptional, (43 reviews)
"This was a very serene and relaxing property to stay at. Loved that our dog was welcome here. Tons of things to do close by and great places to eat…our favorite was The Little Lemon Leaf Diner. The National Wildlife Refuge was also awesome to visit and kayak, we brought our own. Lots of kayaking opportunities right off the property as well. Rock Hall is a quaint little town and people are very friendly."
United States
Amy F.
Serene Waterfront Cottage with dock and gorgeous views.

14. Waterfront! Private Dock, Boat Tie-Up & Near Town

Waterfront! Private Dock, Boat Tie-Up & Near Town
Rock Hall
9.6 out of 10, Exceptional, (9 reviews)
"A beautiful spot."
United States
Laura S.
Waterfront! Private Dock, Boat Tie-Up & Near Town

15. Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Rock Hall
10.0 out of 10, Exceptional, (39 reviews)
"Beautiful, quiet, very charming. Was the perfect little get away we were looking for "
United States
Stephen G.
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

16. Grays Inn Creek Waterfront Pvt Dock Kayaks & View

Grays Inn Creek Waterfront Pvt Dock Kayaks & View
Rock Hall
10.0 out of 10, Exceptional, (10 reviews)
"We enjoyed our stay. There was plenty of room for our large group to eat and play."
United States
Eileen P.
Grays Inn Creek Waterfront Pvt Dock Kayaks & View

17. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
$296 nightly
The price is $328
Nov 10 - Nov 11
Total with taxes and fees
Newly restored apartment in the heart of Chestertown

18. Stay in the landmark Lighthouse!

Stay in the landmark Lighthouse!
Rock Hall
9.8 out of 10, Exceptional, (120 reviews)
"The location was close to town. Enjoyed the lay back vibe of midweek stay."
United States
Barb N.
Stay in the landmark Lighthouse!

19. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
$305 nightly
The price is $338
Nov 30 - Dec 1
Total with taxes and fees
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

20. Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Rock Hall
10.0 out of 10, Exceptional, (58 reviews)
"Great location right on the triathlon route. Super charming town that was fun to bike with kids. Hosts left a great PDF with lots of suggestions for fun activities,"
United States
Chantal C.
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
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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