Kent Island Holiday Rentals, Maryland: Private House Rentals

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

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Our top choices for Kent Island hotels

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

1. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

Rp3.423.184

Rp4.255.129 total

includes taxes & fees

1 Nov - 2 Nov

A large, two-story barn-style building with a covered front porch and a garage.

A dining room with a round table set for six, surrounded by wooden chairs. A fireplace with ornate details is visible, and a large mirror hangs above it.

A large, two-story white house with a porch and multiple windows.

A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

2. Kent Island Resort

Stevensville

Bethany

Rp2.166.367

Rp2.995.796 total

includes taxes & fees

28 Oct - 29 Oct

Two Adirondack chairs facing a calm body of water with a clear sky above.

A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.

A reception desk with a modern design, a digital display, and a check-in counter.

A modern food court with a central island, various food stations, and a yogurt display.

3. Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

Marc

Rp1.968.890

Rp2.185.467 total

includes taxes & fees

25 Oct - 26 Oct

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

4. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

Rp2.720.648

Rp3.019.919 total

includes taxes & fees

18 Oct - 19 Oct

A patio with outdoor seating, overlooking a marina with boats.

A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.

A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.

An indoor swimming pool with clear views of boats and water.

5. Hilton Garden Inn Kent Island Marina

Grasonville

roney

Rp2.482.938

Rp2.756.061 total

includes taxes & fees

19 Oct - 20 Oct

A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.

A restaurant with a counter, seating area, and a clock on the wall.

A kitchenette with a coffee machine, a framed picture, and a potted plant.

An outdoor patio area with picnic tables and a Samuel Adams branded umbrella.

6. Best Western Kent Narrows Inn

Grasonville

Beth

Rp1.931.839

Rp2.144.341 total

includes taxes & fees

14 Oct - 15 Oct

A hotel room with a sofa, armchairs, a TV, a bed, and a large window.

A spacious lobby with a staircase, a reception desk, and a dining area.

A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.

A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.

7. Quality Inn Grasonville near Kent Island

Grasonville

Crystal

Rp1.718.304

Rp1.907.317 total

includes taxes & fees

1 Nov - 2 Nov

A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.

A store with shelves of beverages, a counter with a cash register, and baskets with items.

A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

8. The Westin Annapolis

Annapolis

Bobbi

Rp3.561.901

Rp4.060.567 total

includes taxes & fees

25 Oct - 26 Oct

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.

A modern living room with a sofa, armchairs, a coffee table, and a fireplace.

A restaurant with wooden tables and chairs, a bar area, and a tiled floor.

9. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

Rp1.610.971

Rp1.836.508 total

includes taxes & fees

12 Oct - 13 Oct

An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.

A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.

A modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.

A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.

10. Crowne Plaza Annapolis by IHG

Annapolis

Cynthia

Rp1.968.890

Rp2.244.534 total

includes taxes & fees

11 Oct - 12 Oct

A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.

A spacious atrium with a high ceiling, skylights, and a patterned floor.

A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.

A hotel lobby with a high ceiling, large windows, and a blue and white color scheme. Tables and chairs are arranged for dining or meetings.

11. Graduate by Hilton Annapolis

Annapolis

Mark

Rp2.627.215

Rp2.995.025 total

includes taxes & fees

26 Oct - 27 Oct

A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

An aerial view of a coastal town with a marina, houses, and a bridge in the background.

A marina with multiple boats docked during sunset.

A historic brick building with a red roof, multiple windows, and a central staircase.

12. Historic Inns of Annapolis

Historic District

Ashley

Rp1.533.587

Rp2.360.435 total

includes taxes & fees

1 Nov - 2 Nov

A room with a view of a wooden deck and a gazebo by the water.

A golf course with a water hazard and surrounding trees.

A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.

13. Inn at Perry Cabin

Downtown St. Michaels

Virgilio

Rp9.504.369

Rp10.454.807 total

includes taxes & fees

26 Oct - 27 Oct

A balcony with a table set for two, overlooking a marina with boats.

A hotel room with a large bed, a chair, a small table, and a view of a body of water.

A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.

The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.

14. Annapolis Waterfront Hotel, Autograph Collection

Historic District

William

Rp4.138.249

Rp4.717.603 total

includes taxes & fees

1 Nov - 2 Nov

A two-story house with a porch, a front door, and a small garden area.

A neatly made bed with white linens and a beige pillow, a straw hat on the bed, a wooden nightstand with a small plant and a glass, and a wall-mounted light fixture.

A two-story building with a balcony on the upper floor, outdoor seating with wooden chairs and tables, and a clear view of the surrounding area.

A restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.

15. The Wildset

Downtown St. Michaels

Sarah

Rp4.098.871

Rp4.956.233 total

includes taxes & fees

3 Nov - 4 Nov

A modern lobby with a seating area, a fireplace, and a bookshelf.

A restaurant with a yellow cushioned bench, wooden tables, and chairs.

A hotel room with two beds, a desk with a computer, a TV, and a large window with a view of trees.

A modern bar area with a long counter, bar stools, and shelves stocked with various bottles.

16. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

Rp1.893.356

Rp2.158.426 total

includes taxes & fees

25 Oct - 26 Oct

A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.

A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".

A hotel pool area with two pools, chairs, and a sunshade.

A hotel reception area with a reception desk, a television, and seating area.

17. SpringHill Suites by Marriott Annapolis

Annapolis

Lisa

Rp2.129.981

Rp2.428.178 total

includes taxes & fees

25 Oct - 26 Oct

A modern hotel room with a large bed, a separate bathroom with a bathtub, a desk, and a microwave.

A coffee station with two coffee machines, a coffee press, and various coffee-related items on a wooden counter.

A microwave, a coffee maker, and a refrigerator in a kitchen area.

A hotel with a covered entrance, large columns, and a brick facade.

18. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Omer

Rp1.968.890

Rp2.244.535 total

includes taxes & fees

25 Oct - 26 Oct

A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.

A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.

A bar area with multiple screens displaying sports content, a high ceiling with geometric patterns, and a view of the outside through large windows.

A modern bar area with a long counter and multiple bar stools.

19. Rod 'N' Reel Resort

Chesapeake Beach

Kathleen K

Rp2.587.927

Rp2.872.599 total

includes taxes & fees

20 Oct - 21 Oct

A two-story building with a covered entrance and an American flag.

A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.

A hotel room with two beds, a chair, and a painting on the wall.

A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.

20. St Michaels Inn

St. Michaels

Lynn

Rp1.594.801

Rp1.754.281 total

includes taxes & fees

14 Oct - 15 Oct

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Stay near popular Kent Island attractions

Matapeake State Park

7.6/10 (4 reviews)

Matapeake State Park features serene Chesapeake Bay views from its beach and trails. Enjoy panoramic Bay Bridge vistas while picnicking, or visit the separate dog-friendly beach area.

See properties

Paul Reed Smith Guitars

Witness master luthiers transform raw wood into world-class electric guitars at this renowned factory. The 90-minute guided tour reveals meticulous craftsmanship from wood selection to final assembly.

See properties

Learn more about Kent Island

Cross the Chesapeake Bay Bridge to discover Kent Island's scenic waterfront and fresh seafood restaurants. Kayak through tranquil creeks, cycle the Cross Island Trail, or visit historic Stevensville for a taste of Eastern Shore charm.

See all hotels in Kent Island

Top Kent Island Hotel Reviews

Holiday Inn Express & Suites Annapolis by IHG

8/10 Good

"clean room. small bathroom but clean. wi-fi good. breakfast was good. staff helpful. overall, a good stay for one night. walkable area - close to a shopping area."

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"This was a nice spot to land while we visited Annapolis family and friends. Comfortable and very nice staff - especially in the dining room!"

Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"Staff was great, hotel needs real renovation seems like they've done a lot of patch work. Parking should be complimentary for people staying in the hotel or a discounted rate. $35 a day for parking at the hotel you're staying at is crazy. There's very limited parking to begin with."

Best Western Annapolis

8/10 Good

"Friendly and respectful staff, clean premises, well stocked breakfast, rooms need better maintenance."

Sonesta ES Suites Annapolis

10/10 Excellent

"It is an excellent value for the cost!"

St Michaels Inn

10/10 Excellent

"Late night manager was extremely helpful!"

Kent Island Resort

10/10 Excellent

"Excellent time, loved the property and speaking with the staff who were always helpful and friendly. Our room was beautiful and just added to the experience."

More cheap stays in Kent Island

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

Rp1.288.567

Rp1.430.309 total

15 Oct - 16 Oct

includes taxes & fees

Best Western Annapolis

2520 Riva Rd Annapolis MD

Rp1.433.889

Rp1.634.634 total

25 Oct - 26 Oct

includes taxes & fees

7.8/10 Good! (1,000 reviews)

St Michaels Inn

1228 S Talbot Street St. Michaels MD

Rp1.594.801

Rp1.754.281 total

14 Oct - 15 Oct

includes taxes & fees

Microtel Inn & Suites by Wyndham Gambrills/Odenton

2525 Evergreen Rd. Gambrills MD

Rp1.673.557

Rp1.907.855 total

1 Nov - 2 Nov

includes taxes & fees

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

Rp1.931.839

Rp2.144.341 total

14 Oct - 15 Oct

includes taxes & fees

8/10 Very good! (1,000 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

Rp1.968.890

Rp2.244.535 total

25 Oct - 26 Oct

includes taxes & fees

8.4/10 Very good! (1,000 reviews)

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Find hotels in Kent Island, MD from Rp1.430.309

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Kent Island

Check prices for these dates

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Our top choices for Kent Island hotels

1. The Inn at Chesapeake Bay Beach Club

2. Kent Island Resort

3. Holiday Inn Express Annapolis East-Kent Island by IHG

4. Hyatt Place Kent Narrows & Marina

5. Hilton Garden Inn Kent Island Marina

6. Best Western Kent Narrows Inn

7. Quality Inn Grasonville near Kent Island

8. The Westin Annapolis

9. DoubleTree by Hilton Hotel Annapolis

10. Crowne Plaza Annapolis by IHG

11. Graduate by Hilton Annapolis

12. Historic Inns of Annapolis

13. Inn at Perry Cabin

14. Annapolis Waterfront Hotel, Autograph Collection

15. The Wildset

16. Hilton Garden Inn Annapolis Downtown

17. SpringHill Suites by Marriott Annapolis

18. Holiday Inn Express & Suites Annapolis by IHG

19. Rod 'N' Reel Resort

20. St Michaels Inn

Stay near popular Kent Island attractions

Matapeake State Park

Paul Reed Smith Guitars

Learn more about Kent Island

Top Kent Island Hotel Reviews

Holiday Inn Express & Suites Annapolis by IHG

DoubleTree by Hilton Hotel Annapolis

Hilton Garden Inn Annapolis Downtown

Best Western Annapolis

Sonesta ES Suites Annapolis

St Michaels Inn

Kent Island Resort

More cheap stays in Kent Island

Red Roof Inn & Suites Chestertown

Best Western Annapolis

St Michaels Inn

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Best Western Kent Narrows Inn

Holiday Inn Express & Suites Annapolis by IHG

Explore a world of travel with Expedia

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