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Holiday Rentals in Kent County Kent County Car Hire Kent County Holidays

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

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

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Top Cities in Kent County

An aerial view of a town with a river, buildings, and surrounding greenery.

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25 Oct - 26 Oct

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Our top choices for Kent County hotels

A campfire in a stone fire pit by a lakeside at sunset.

A marina with boats docked, a sandy beach with umbrellas, and a pier extending into the water.

A spacious room with a large window, a seating area with a sofa and armchairs, a small table with a plant, and a display of various items including a mannequin and shelves with products.

A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

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, (124 reviews)

8.0/10

Very good

(124 reviews)

"Nice restairant and bar"

"Nice restairant and bar"

United States

Steve allen

The price is HK$847

HK$847

HK$968 total

includes taxes & fees

27 Oct - 28 Oct

The Lodge at Great Oak Landing

A hotel lobby with a fireplace, seating area, and a television.

A hotel reception area with a reception desk, a seating area, and a hallway leading to other rooms.

A hotel room with a bed, a sofa, a dining table, and a small round table.

A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.

2. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property

Chestertown

8.6 out of 10, Excellent, (995 reviews)

8.6/10

Excellent

(995 reviews)

"Property was quiet and clean and close to town."

"Property was quiet and clean and close to town."

United States

Roberta

The price is HK$770

HK$770

HK$854 total

includes taxes & fees

15 Nov - 16 Nov

Comfort Inn & Suites Chestertown

A living room with a fireplace, a television, and a stone accent wall.

A hotel room with a sofa, two beds, a painting, and a lamp.

A hotel room with a bed, a desk, a chair, a sofa, and a painting on the wall.

A multi-story brick building with a covered entrance and a parking lot.

3. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property

Chestertown

7.2 out of 10, Good, (511 reviews)

7.2/10

Good

(511 reviews)

"Friendly staff, plenty of parking spaces,family friendly. The building is old but would do some renovation. Furniture needs replacement."

"Friendly staff, plenty of parking spaces,family friendly. The building is old but would do some renovation. Furniture needs replacement."

United States

Mary

The price is HK$565

HK$565

HK$627 total

includes taxes & fees

1 Nov - 2 Nov

Red Roof Inn & Suites Chestertown

A boat deck with a white bench and a view of a calm lake and distant trees.

A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.

A buffet with various food items including fruits, pastries, and salads.

A modern living room with a large sofa, a small armchair, a coffee table, and a fireplace.

4. Inn at Huntingfield Creek

Inn at Huntingfield Creek

3.5 star property

Rock Hall

10.0 out of 10, Exceptional, (74 reviews)

10/10

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"

"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 HK$1,099

HK$1,099

HK$1,220 total

includes taxes & fees

16 Nov - 17 Nov

Inn at Huntingfield Creek

A row of motel rooms with stone walls and red doors.

A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.

A living room with two patterned armchairs, a wooden coffee table, and a standing fan.

A living room with a wooden cabinet, a television, a sofa, and a dining table.

5. Driftwood Inn

2.0 star property

Chestertown

5.4 out of 10, (183 reviews)

5.4/10

(183 reviews)

"It was a nice, clean place to stay the night."

"It was a nice, clean place to stay the night."

United States

Kathy

The price is HK$498

HK$498

HK$553 total

includes taxes & fees

26 Oct - 27 Oct

A covered outdoor seating area with a view of a landscaped garden and a body of water.

A two-story house with a balcony, a porch with potted plants, and a flag.

A living room with a fireplace, a bookshelf, and a striped sofa.

A marina with numerous sailboats docked in a row, connected by a wooden walkway.

6. Inn at Haven Harbour

Inn at Haven Harbour

3.0 star property

Rock Hall

7.8 out of 10, Good, (6 reviews)

7.8/10

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. "

"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

A two-story house with a covered porch, a staircase, and a garden area.

A row of stationary bicycles with green frames and white seats, parked outdoors.

A dining room with a long wooden table set for six, surrounded by chairs. There are framed pictures on the walls, a window with a view of trees, and a sofa in the background.

A garden with a lawn and a table with chairs under a canopy.

7. Haven Point Inn and Gallery

Haven Point Inn and Gallery

2.0 star property

Rock Hall

9.6 out of 10, Exceptional, (17 reviews)

9.6/10

Exceptional

(17 reviews)

"Host is fantastic. Great room with garden view. Breakfast made to order. Beautiful art gallery."

"Host is fantastic. Great room with garden view. Breakfast made to order. Beautiful art gallery."

United States

Joe

The price is HK$1,048

HK$1,048

HK$1,163 total

includes taxes & fees

27 Oct - 28 Oct

Haven Point Inn and Gallery

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

A bedroom with a large bed, a chandelier, and a bedside table with a tray of items.

A garden with a pond, a wooden deck, and a stone pathway.

A person sitting on a wooden deck by a calm body of water, surrounded by greenery.

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, (30 reviews)

9.8/10

Exceptional

(30 reviews)

"Convenient, clean, super friendly host, loved it. Highly recommend!!!"

"Convenient, clean, super friendly host, loved it. Highly recommend!!!"

United States

Quinton

The price is HK$533

HK$533

HK$981 total

includes taxes & fees

28 Oct - 29 Oct

Guest Suite for up to 2 in a Victorian on the Chester River

A house with a blue front door, two windows, and a small porch.

A living room with a glass-top coffee table, a blue sofa, a patterned armchair, and a television on a wooden stand.

A garden with a statue, various shrubs, and a flower bed.

A grassy outdoor seating area with Adirondack chairs and a small table, surrounded by trees.

9. 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)

10/10

Exceptional

(30 reviews)

"Great property! Great accommodations! Wonderful host"

"Great property! Great accommodations! Wonderful host"

United States

lisa p.

The price is HK$972

HK$972

HK$2,303 total

includes taxes & fees

1 Nov - 2 Nov

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

A building with a gabled roof and a circular vent on the roof.

A room with a Galaxy S22, a table with chairs, a refrigerator, and a window with curtains.

A hotel room with a window, a door with a mirror, a wall-mounted thermostat, and a warning sign about overheating.

A bathroom with a glass-enclosed shower, a sink, and a mirror.

10. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall

10.0 out of 10, Exceptional, (67 reviews)

10/10

Exceptional

(67 reviews)

"Perfect little place for our weekend stay!"

"Perfect little place for our weekend stay!"

United States

Diane V.

The price is HK$1,569

HK$1,569

HK$2,476 total

includes taxes & fees

26 Oct - 27 Oct

BAYSIDE BUNGALOW

A wooden deck with outdoor seating, overlooking a lake with boats and a dock.

A cozy living room with a sofa, two chairs, a coffee table with candles, a decorative wall piece, and a window with blinds.

A bedroom with a window covered by blinds, a bed with white bedding, and a framed picture on the wall.

A kitchen with a stove, microwave, kettle, and a sign that says "enjoy the journey."

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, (122 reviews)

10/10

Exceptional

(122 reviews)

"Absolutely perfect place to retreat. The house are genuinely loving, and it shows in every detail about the cottage."

"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

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

A swimming pool with a curved edge, surrounded by a brick patio and a hedge.

A building with a balcony and large windows, surrounded by trees and a fence.

A closet with a wooden floor, a white door, and a blue bag on top.

12. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown

9.8 out of 10, Exceptional, (130 reviews)

9.8/10

Exceptional

(130 reviews)

"A beautiful and comfortable accomodations."

"A beautiful and comfortable accomodations."

United States

John R.

The price is HK$776

HK$776

HK$1,246 total

includes taxes & fees

26 Oct - 27 Oct

First Floor Studio Apartment in Historic Chestertown

A wooden dock leading to a house with a red roof, surrounded by lush greenery and a calm body of water.

A room with a wooden desk, a wicker chair, and a laptop.

A two-story house with a balcony and a wrap-around porch.

A kitchen with white cabinets, a granite countertop, a gas stove, a microwave, and a refrigerator.

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)

9.6/10

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."

"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.

A boat on the ocean during sunset.

A house with a porch, a flag, and a bird feeder.

A single-story house with a covered porch and a small attached garage.

A kitchen with wooden cabinets, a white stove, a refrigerator, and a window with a view of greenery outside.

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)

9.8/10

Exceptional

(70 reviews)

"We have always enjoyed our stays here."

"We have always enjoyed our stays here."

United States

David G.

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

A deck with a table and chairs, a blue chair, a bench, and a wooden fence.

A compact living space with a kitchenette, a dining area, and a seating area with a sofa.

A small, single-story building with a gabled roof and a front porch.

A sunset over a calm sea with a rocky outcrop in the foreground.

15. 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)

10/10

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,"

"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

A beach view from a covered area with a wooden deck, sandy beach, rocky shoreline, and a pier in the distance.

A modern kitchen with a central island, bar stools, and pendant lighting.

A historic ship docked at a pier with a lifebuoy and a small lighthouse structure.

A narrow brick pathway leading to a patio area with a table and chairs, surrounded by lush greenery and a wooden fence.

16. 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)

9.6/10

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!"

"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!

A hammock suspended from a wooden structure on a wooden deck with a view of trees and a railing.

A spiral staircase with lights, surrounded by plants and a wooden deck.

A living room with a beige sofa, a green ottoman, a woven basket, and a potted plant.

A marina at sunset with boats docked and a clear sky.

17. 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)

10/10

Exceptional

(39 reviews)

"Beautiful, quiet, very charming. Was the perfect little get away we were looking for "

"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!

A swimming pool surrounded by lush greenery and various plants.

A living room with a white sofa, a framed picture on the wall, a television, and a dining area with red chairs.

A cozy room with a round table, red chairs, a cabinet, and a sign welcoming visitors to the collage.

A living room with a white sofa, a television, a wooden cabinet, and a wicker chair.

18. Charming cottage with Pool Access and WiFi in lovely Rock Hall

Charming cottage with Pool Access and WiFi in lovely Rock Hall

Rock Hall

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"Wonderful 2 night stay at this charming cottage in Rock Hall. We would definitely recommend. "

"Wonderful 2 night stay at this charming cottage in Rock Hall. We would definitely recommend. "

United States

andrew h.

Charming cottage with Pool Access and WiFi in lovely Rock Hall

A room with large windows, a dining table, two patterned chairs, and a potted plant.

A spacious living room with a ceiling fan, large windows, and a view of the outdoors.

A two-story house with a large deck and a covered porch.

A spacious living room with a dark blue sectional sofa, wooden flooring, large windows, and a mounted TV.

19. 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)

10/10

Exceptional

(10 reviews)

"We enjoyed our stay. There was plenty of room for our large group to eat and play."

"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

Relax, Chat, or Watch TV in the Oversized Sunroom

A bedroom with a bed, bedside tables, a ceiling fan, a TV, a chair, and a kitchenette.

Lounge Chairs with Waterfront Views

A modern kitchen with white cabinetry, a large island with bar stools, stainless steel appliances, and recessed ceiling lights.

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

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

Rock Hall

9.6 out of 10, Exceptional, (8 reviews)

9.6/10

Exceptional

(8 reviews)

"A beautiful spot."

"A beautiful spot."

United States

Laura S.

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

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.

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.

View all properties

Showing deals for:6 Nov - 8 Nov

Image gallery for The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 star property

Chestertown

8.0/10Very good (124 reviews)

Member Price available

Price is HK$926

HK$926

HK$2,118 total

HK$2,118 total

includes taxes & fees

Sign in for Member Price

The Lodge at Great Oak Landing

Image gallery for Life is better at the RIVER!--Cozy waterfront cottage

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

Galena

10/10Exceptional (122 reviews)

10% off

Price is HK$1,306

HK$1,306

HK$4,589 total

HK$4,589 total

includes taxes & fees

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

Image gallery for Be persuaded to experience this vintage cottage by the Sassa

Be persuaded to experience this vintage cottage by the Sassa

Galena

9.4/10Exceptional (15 reviews)

10% off

Price is HK$2,082

HK$2,082

HK$6,941 total

HK$6,941 total

includes taxes & fees

Be persuaded to experience this vintage cottage by the Sassa

Image gallery for Haven Point Inn and Gallery

Haven Point Inn and Gallery

2.0 star property

Rock Hall

9.6/10Exceptional (17 reviews)

10% off

Price is HK$1,398

HK$1,398

HK$3,103 total

HK$3,103 total

includes taxes & fees

Haven Point Inn and Gallery

Image gallery for Inn at Huntingfield Creek

Inn at Huntingfield Creek

3.5 star property

Rock Hall

10/10Exceptional (74 reviews)

10% off

Price is HK$2,364

HK$2,364

HK$5,247 total

HK$5,247 total

includes taxes & fees

Inn at Huntingfield Creek

Image gallery for Historic Downtown Garden Oasis with Private Patio

Historic Downtown Garden Oasis with Private Patio

Chestertown

10/10Exceptional (58 reviews)

10% off

Price is HK$1,468

HK$1,468

HK$3,683 total

HK$3,683 total

includes taxes & fees

Historic Downtown Garden Oasis with Private Patio

Image gallery for Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall

Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall

Rock Hall

10/10Exceptional (12 reviews)

10% off

Price is HK$2,117

HK$2,117

HK$5,512 total

HK$5,512 total

includes taxes & fees

Spacious & charming 3-bedroom rancher in Ferry Park section of Rock Hall

Image gallery for This is truly a Baydream!

This is truly a Baydream!

Rock Hall

10/10Exceptional (41 reviews)

10% off

Price is HK$1,835

HK$1,835

HK$5,912 total

HK$5,912 total

includes taxes & fees

This is truly a Baydream!

Image gallery for Charming cottage with Pool Access and WiFi in lovely Rock Hall

Charming cottage with Pool Access and WiFi in lovely Rock Hall

Rock Hall

10/10Exceptional (8 reviews)

20% off

Price is HK$1,098

HK$1,098

HK$3,715 total

HK$3,715 total

includes taxes & fees

Charming cottage with Pool Access and WiFi in lovely Rock Hall

Image gallery for Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown

Chestertown

10/10Exceptional (34 reviews)

10% off

Price is HK$2,329

HK$2,329

HK$6,423 total

HK$6,423 total

includes taxes & fees

Newly restored apartment in the heart of Chestertown

Image gallery for Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

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

Rock Hall

10/10Exceptional (39 reviews)

10% off

Price is HK$1,676

HK$1,676

HK$5,300 total

HK$5,300 total

includes taxes & fees

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

Image gallery for Prime Rock Hall Location!! Restaurants, Boat Ramp, & Beach Within Minutes Away!!

Prime Rock Hall Location!! Restaurants, Boat Ramp, & Beach Within Minutes Away!!

Rock Hall

9.6/10Exceptional (5 reviews)

10% off

Price is HK$2,248

HK$2,248

HK$7,343 total

HK$7,343 total

includes taxes & fees

Prime Rock Hall Location!! Restaurants, Boat Ramp, & Beach Within Minutes Away!!

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

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

Rock Hall

10/10Exceptional (25 reviews)

10% off

Price is HK$3,243

HK$3,243

HK$9,519 total

HK$9,519 total

includes taxes & fees

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

Image gallery for Cute waterfront apartment -- 8 min from the beach!

Cute waterfront apartment -- 8 min from the beach!

Rock Hall

9.6/10Exceptional (11 reviews)

10% off

Price is HK$1,482

HK$1,482

HK$4,977 total

HK$4,977 total

includes taxes & fees

Cute waterfront apartment -- 8 min from the beach!

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Top Kent County Hotel Reviews

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

10/10 Excellent

"Facility excellent for moderate price."

David 3-night trip

Posted 2 hours ago

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

Holiday Inn Baltimore BWI Airport by IHG

Holiday Inn Baltimore BWI Airport by IHG

10/10 Excellent

"Nice staff"

thomas 1-night trip

Posted 4 hours ago

Holiday Inn Baltimore BWI Airport by IHG

Lord Baltimore Hotel

Lord Baltimore Hotel

10/10 Excellent

"Love this hotel"

Erin 2-night trip

Posted 7 hours ago

Lord Baltimore Hotel

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