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

Vacation Homes in Kent County

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Kent County vacation homes

A beach with chairs and a pier in the background.

1. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is AED 694
AED 1,734 total
includes taxes & fees
20 Oct - 21 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A rooftop terrace with a fire pit and seating area, overlooking a cityscape at night.

2. Rooftop Deck Escape! Free Parking!

Rooftop Deck Escape! Free Parking!
South Baltimore
8.6 out of 10, Excellent, (73 reviews)
"Great location loved the rooftop deck and had fun playing the shuffle board table."
United States
Heather M.
The price is AED 326
AED 1,009 total
includes taxes & fees
20 Oct - 21 Oct
Rooftop Deck Escape! Free Parking!
A room with a fireplace, a mirror, a wreath, and a potted plant.

3. Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Historic District
9.4 out of 10, Exceptional, (22 reviews)
"Good location convenient to old town Annapolis and even can walk there"
United States
Thomas B.
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
A waterfront restaurant with tables and an umbrella, a dock with a boat, and a sign indicating emergency exit only.

4. Waterfront Retreat home with Deck, Dock & Sunset Views. Your Marley Creek Escape

Waterfront Retreat home with Deck, Dock & Sunset Views. Your Marley Creek Escape
Marley
9.4 out of 10, Exceptional, (10 reviews)
"Victor and Rose are fantastic hosts! We’ve booked with them multiple times and their property is just perfect for our group."
United States
MacKendrie P.
The price is AED 801
AED 1,030 total
includes taxes & fees
18 Oct - 19 Oct
Waterfront Retreat home with Deck, Dock & Sunset Views. Your Marley Creek Escape
A living room with a sofa, a wooden coffee table, a red chair, a white cabinet with glass doors, and a chandelier.

5. Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels
Downtown St. Michaels
9.6 out of 10, Exceptional, (70 reviews)
"Centrally located, this little dollhouse is perfect for a couple or small family. Easily in walking distance to all important locations in St Michael’s. The A/C works great too!"
United States
Bonnie T.
Dollhouse in Central Historic St Michaels
A living room with a sofa, armchair, coffee table, dining table, chairs, and framed artwork on the wall.

6. Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Crofton
9.8 out of 10, Exceptional, (123 reviews)
"We really enjoyed our stay! Everything was clean and the parking was great. Location was perfect for all of our local travel plans."
United States
Kenneth A.
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

7. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (27 reviews)
"The property was very clean nice open kitchen and comfortable rooms . Very nice experience definitely recommend."
United States
Antonio
The price is AED 241
AED 769 total
includes taxes & fees
19 Oct - 20 Oct
Cute, Cozy 2-bedroom house near Annapolis with water access
A modern kitchen with white cabinetry, a stainless steel refrigerator, wooden shelves, and pendant lighting.

8. Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Cape Saint Claire
9.8 out of 10, Exceptional, (56 reviews)
"Place was awesome and Erin, the property manager, was so kind"
United Kingdom
Carter S.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
A hot tub with a view of a lake and a metal fence.

9. Sailor's Sunrise Cottage - Chesapeake Bay

Sailor's Sunrise Cottage - Chesapeake Bay
Perryville
9.2 out of 10, Wonderful, (65 reviews)
"Excellent location with beautiful sunrises and water views!"
United States
Kirk B.
Sailor's Sunrise Cottage - Chesapeake Bay
A view of a lake with trees and a wooden structure in the foreground.

10. Sunset River Cottage

Sunset River Cottage
Elkton
8.8 out of 10, Excellent, (30 reviews)
"The property was just what we needed. Very quiet, laid back and the pier was great for fishing!"
United States
Ray D.
Sunset River Cottage
An outdoor patio with two tables set up, surrounded by ivy-covered walls and string lights.

11. Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Historic District
10.0 out of 10, Exceptional, (263 reviews)
"Great location in downtown Annapolis! House was clean and comfortable. We had a great stay."
United States
Kristen P.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.

12. 13 Mi to Annapolis: Dog-Friendly Home w/ Fire Pit!

13 Mi to Annapolis: Dog-Friendly Home w/ Fire Pit!
Crofton
10.0 out of 10, Exceptional, (35 reviews)
"Cute house in a great neighborhood. Especially appreciated the screened porch."
United States
Robert H.
13 Mi to Annapolis: Dog-Friendly Home w/ Fire Pit!
A spacious living room with a wooden floor, a large leather rug, a sofa, a coffee table, and a TV mounted on the wall.

13. Luxury Townhouse . Roof Deck . Patios . Parking

Luxury Townhouse . Roof Deck . Patios . Parking
Fells Point
9.4 out of 10, Exceptional, (28 reviews)
"We had a rocky start at check in but Ally was responsive and helpful with working out the kinks. Once we did get settled in the stay was great. The garage parking is an excellent amenity as well as the roof top deck."
United States
Christy B.
Luxury Townhouse . Roof Deck . Patios . Parking
A wooden dock leading to a house with multiple windows and a well-lit interior.

14. Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Easton
10.0 out of 10, Exceptional, (113 reviews)
"Spectacular property...we can't wait to come back again next year!!"
United States
Matthew P.
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
A waterfront building with a pool, outdoor seating, and a view of the city.

15. 3-bedroom Townhome in Exciting Corner of Fells Point!

3-bedroom Townhome in Exciting Corner of Fells Point!
Fells Point
9.8 out of 10, Exceptional, (9 reviews)
"If someone needs a place to stay in Baltimore, this VRBO is in a wonderful location! The price is good, and the communication with the owner is stellar."
United States
Anita S.
3-bedroom Townhome in Exciting Corner of Fells Point!
A living room with a large window, a sofa, and a dining table.

16. 5BR Chesapeake Waterfront Estate with Private Dock

5BR Chesapeake Waterfront Estate with Private Dock
Perryville
10.0 out of 10, Exceptional, (13 reviews)
"Excellent communication with our host. Our family had a great mini vacation."
United States
Wayne W.
5BR Chesapeake Waterfront Estate with Private Dock
A modern kitchen with white cabinets, a central island with bar stools, and a view to the outside.

17. Bright & Beautiful 4BR Home + Parking, Walk to Harbor & Stadiums

Bright & Beautiful 4BR Home + Parking, Walk to Harbor & Stadiums
Otterbein
10.0 out of 10, Exceptional, (4 reviews)
"Wonderful host. Excellent communication. Beautiful home. Convenient to stadiums. Cozy house and beautiful design. Highly recommend!"
United States
Maureen T.
Bright & Beautiful 4BR Home + Parking, Walk to Harbor & Stadiums
A compact living space with a sofa, a small table, a TV, and a fan.

18. Charming 2-bedroom house with fitness room and AC in Glen Burnie

Charming 2-bedroom house with fitness room and AC in Glen Burnie
Glen Burnie
9.0 out of 10, Wonderful, (12 reviews)
"Very private and cozy stay!"
United States
Anna K.
Charming 2-bedroom house with fitness room and AC in Glen Burnie
A modern living room with a staircase, a dining area, and a kitchen in the background.

19. Hudson house

Hudson house
4.0 star property
Canton
7.6 out of 10, Good, (5 reviews)
"The condo was really nice and clean"
United States
Thelma
Hudson house
A building with a porch, a sign reading "Ristorante St. Michaels," and a brick sidewalk.

20. Grace Cottage, St Michaels Walk to everything!

Grace Cottage, St Michaels Walk to everything!
Downtown St. Michaels
10.0 out of 10, Exceptional, (16 reviews)
Grace Cottage, St Michaels Walk to everything!
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 Kent County Hotel Reviews

Holiday Inn Baltimore BWI Airport by IHG

Holiday Inn Baltimore BWI Airport by IHG

10/10 Excellent
"We stayed here when our flight was canceled. They had a shuttle to and from the airport we got in pretty late on Saturday night, but dinner was still available and the food was delicious."
carolyn 1-night trip
Posted 1 hour ago
Holiday Inn Baltimore BWI Airport by IHG

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