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Our top choices for Kent County hotels

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (891 reviews)
"Staying is peaceful and the rooms clean."
United States
Robert
The price is €111
includes taxes & fees
15 Apr - 16 Apr
Comfort Inn & Suites Chestertown

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (62 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
United States
Sandra
The price is €135
includes taxes & fees
29 Mar - 30 Mar
Inn at Huntingfield Creek

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (432 reviews)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
The price is €77
includes taxes & fees
7 Apr - 8 Apr
Red Roof Inn & Suites Chestertown

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77 reviews)
"Very nice rooms, "
United States
Stephania
The price is €107
includes taxes & fees
29 Mar - 30 Mar
The Lodge at Great Oak Landing

Inn at Haven Harbour

Inn at Haven Harbour
3.0 star property
Rock Hall
8.6 out of 10, Excellent, (4 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

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"Every thing was great"
United States
lesia k.
The price is €141
includes taxes & fees
6 Apr - 7 Apr
First Floor Studio Apartment in Historic Chestertown

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
The price is €149
includes taxes & fees
21 Apr - 22 Apr
Haven Point Inn and Gallery

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
9.6 out of 10, Exceptional, (20 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is €112
includes taxes & fees
1 Apr - 2 Apr
Guest Suite for up to 2 in a Victorian on the Chester River

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
Driftwood Inn

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, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is €248
includes taxes & fees
27 Mar - 28 Mar
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Grays Inn Creek Waterfront Pvt. Dock Kayaks & View

Grays Inn Creek Waterfront Pvt. Dock Kayaks & View
Rock Hall
10.0 out of 10, Exceptional, (3 reviews)
"Really beautiful property right on the lake. Fantastic dinning space, where everyone gathered for meals."
United States
Emma A.
Grays Inn Creek Waterfront Pvt. Dock Kayaks & View

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
BAYSIDE BUNGALOW

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, (30 reviews)
"Beautiful home. Great little town. I would definitely stay again"
United States
Thomas
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

Blue Heron Farm Waterfront Chalet

Blue Heron Farm Waterfront Chalet
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"We had an amazing stay on this picturesque slice of the Eastern Shore. The house is perfectly situated for stunning sunsets with ample outdoor space. We loved being able to cook out dinner while taking in wildlife and the water.Ben, our host, was quick to respond to questions and left a super helpful binder of suggestions. "
United States
Amy G.
Blue Heron Farm Waterfront Chalet

Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11

Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11
Rock Hall
10.0 out of 10, Exceptional, (20 reviews)
"We loved staying here! The house is beautiful and is located in a lovely area. We will definitely stay again!"
United States
Barbara C.
Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Chestertown
10.0 out of 10, Exceptional, (16 reviews)
"We loved the location in the woods and the wildlife we saw. It was incredibly private. "
United States
Michelle P.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

River Cottage, Chestertown

River Cottage, Chestertown
Chestertown
9.0 out of 10, Wonderful, (2 reviews)
"The house was amazing. The amenities were everything as advertised. The owners were also very friendly. We loved staying here. "
United States
Bedlum B.
River Cottage, Chestertown

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

Waterfront! Private Dock, Boat Tie-Up & Near Town
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"A beautiful spot."
United States
Laura S.
Waterfront! Private Dock, Boat Tie-Up & Near Town

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
The price is €268
includes taxes & fees
20 Apr - 21 Apr
Waterfront Retreat with Private Dock and Beach

WATERFRONT right on a BEACH

WATERFRONT right on a BEACH
Rock Hall
10.0 out of 10, Exceptional, (51 reviews)
"Beautiful house and property. Tracy is a very helpful and welcoming host. Will definitely be returning!"
United States
Ryan B.
WATERFRONT right on a BEACH
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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