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, (116 reviews)
"This is a wonderful facility for a couple or family. The restaurant is just "ok"."
United States
Sandra
The price is CA $154
CA $176 total
includes taxes & fees
Oct 7 - Oct 8
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, (989 reviews)
"This was a very well maintained place and the breakfast was really good."
United States
Amy
The price is CA $145
CA $161 total
includes taxes & fees
Nov 1 - Nov 2
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, (504 reviews)
"Very nice hotel. Have stayed here every year for the Pirates and Wenches Festival in Rock Hall."
United States
Linda
The price is CA $103
CA $114 total
includes taxes & fees
Oct 11 - Oct 12
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
The price is CA $228
CA $254 total
includes taxes & fees
Nov 1 - Nov 2
Inn at Huntingfield Creek

5. Inn at Haven Harbour

Inn at Haven Harbour
3.0 star property
Rock Hall
8.0 out of 10, Very good, (5 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

6. Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
9.6 out of 10, Exceptional, (15 reviews)
"Host is fantastic. Great room with garden view. Breakfast made to order. Beautiful art gallery."
United States
Joe
The price is CA $190
CA $211 total
includes taxes & fees
Oct 6 - Oct 7
Haven Point Inn and Gallery

7. 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
The price is CA $90
CA $100 total
includes taxes & fees
Oct 5 - Oct 6
Driftwood Inn

8. 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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is CA $168
CA $410 total
includes taxes & fees
Oct 5 - Oct 6
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

9. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (66 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is CA $285
CA $450 total
includes taxes & fees
Oct 5 - Oct 6
BAYSIDE BUNGALOW

10. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (129 reviews)
"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"
United States
Charr
The price is CA $141
CA $226 total
includes taxes & fees
Oct 5 - Oct 6
First Floor Studio Apartment in Historic Chestertown

11. 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, (28 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 $97
CA $178 total
includes taxes & fees
Oct 5 - Oct 6
Guest Suite for up to 2 in a Victorian on the Chester River

12. 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, (122 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

13. Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Rock Hall
9.6 out of 10, Exceptional, (14 reviews)
"We had a fantastic weekend in Rock Hall. Oyster Cottage had every thing we needed for a great family getaway! Diane was very helpful prior to our stay. We will definitely book here again!"
United States
Julie R.
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

14. Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Rock Hall
9.8 out of 10, Exceptional, (70 reviews)
"We have always enjoyed our stays here."
United States
David G.
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

15. Serene Waterfront Cottage with dock and gorgeous views.

Serene Waterfront Cottage with dock and gorgeous views.
Rock Hall
9.6 out of 10, Exceptional, (42 reviews)
"Nice place with everything I could want. Would stay there again!"
United States
Eric H.
Serene Waterfront Cottage with dock and gorgeous views.

16. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is CA $227
CA $278 total
includes taxes & fees
Nov 2 - Nov 3
Beachcomber Suite

17. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (5 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
Bayside Cottage steps from Rock Hall Harbor

18. Be persuaded to experience this vintage cottage by the Sassa

Be persuaded to experience this vintage cottage by the Sassa
Galena
9.4 out of 10, Exceptional, (15 reviews)
"Had a lovely peaceful stay. Great amenities."
United States
Joe S.
Be persuaded to experience this vintage cottage by the Sassa

19. 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, (38 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!

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, (56 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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