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

A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

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

1. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

5.286.864 ₫

6.527.722 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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

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.

2. Kent Island Resort

Stevensville

Bethany

3.138.623 ₫

4.340.297 ₫ 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 Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

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

2.850.760 ₫

3.164.343 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

An outdoor event area with round tables and a view of the water.

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

4. Hyatt Place Kent Narrows & Marina

Grasonville

Joseph

3.939.232 ₫

4.372.547 ₫ total

includes taxes & fees

4 Nov - 5 Nov

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

A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.

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.

5. Hilton Garden Inn Kent Island Marina

Grasonville

Charles

3.591.439 ₫

3.986.497 ₫ total

includes taxes & fees

20 Oct - 21 Oct

A hotel room with a bed, a chair, a nightstand, a lamp, and a painting on the wall.

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

A reception desk with a clock, framed pictures, and a sign for express checkout.

6. Best Western Kent Narrows Inn

Grasonville

Wesley

2.329.330 ₫

2.585.556 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.

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

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

7. Quality Inn Grasonville near Kent Island

Grasonville

Crystal

2.340.733 ₫

2.598.214 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

8. The Westin Annapolis

Annapolis

Bobbi

5.157.284 ₫

5.879.304 ₫ total

includes taxes & fees

27 Oct - 28 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 restaurant with wooden tables and chairs, a bar area, and a tiled floor.

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

9. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

2.741.654 ₫

3.125.486 ₫ total

includes taxes & fees

18 Oct - 19 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 historic brick building with a red roof, multiple windows, and a central staircase.

A spacious indoor area with brick walls, multiple tables and chairs, and string lights.

10. Historic Inns of Annapolis

Historic District

Ashley

2.220.483 ₫

3.417.678 ₫ total

includes taxes & fees

21 Oct - 22 Oct

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

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.

A multi-story hotel with a brick facade, large windows, and an American flag.

11. Crowne Plaza Annapolis by IHG

Annapolis

Jose

2.773.012 ₫

3.161.234 ₫ total

includes taxes & fees

11 Nov - 12 Nov

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

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.

A hotel room with a large bed, a chair, a desk, and a television.

12. Inn at Perry Cabin

Downtown St. Michaels

Virgilio

13.761.396 ₫

15.137.535 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

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

A modern lounge area with a blue sofa, red chairs, and plaid armchairs. A coffee table with books and a vase of flowers is in the center. Large windows offer a view of a brick building with awnings.

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

13. Graduate by Hilton Annapolis

Annapolis

Mark

3.806.299 ₫

4.339.181 ₫ 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.

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

A waterfront area with boats docked, a clear sky, and buildings in the background.

14. Annapolis Waterfront Hotel, Autograph Collection

Historic District

William

5.788.022 ₫

6.598.346 ₫ total

includes taxes & fees

2 Nov - 3 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 restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.

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.

15. The Wildset

Downtown St. Michaels

Sarah

5.934.764 ₫

7.176.140 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

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

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

A buffet with various food items, including omelets and baked goods, in stainless steel containers.

16. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Omer

2.617.516 ₫

2.983.968 ₫ total

includes taxes & fees

18 Oct - 19 Oct

17. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

2.741.394 ₫

3.125.190 ₫ 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 room with a bed, a desk, a chair, a coffee machine, and a tray table.

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

18. SpringHill Suites by Marriott Annapolis

Annapolis

Lisa

3.085.908 ₫

3.517.935 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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.

19. St Michaels Inn

St. Michaels

Lynn

2.075.872 ₫

2.283.459 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

A staircase with a wooden handrail, a blue wall, and a ceiling light fixture.

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

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

20. Rod 'N' Reel Resort

Chesapeake Beach

Kathleen K

3.747.064 ₫

4.159.242 ₫ total

includes taxes & fees

21 Oct - 22 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.

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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

Crowne Plaza Annapolis by IHG

10/10 Excellent

"Clean room. Great breakfast."

Best Western Annapolis

8/10 Good

"Noisy balcony"

Historic Inns of Annapolis

10/10 Excellent

"We stayed here overnight so that we didn't have to travel from MoCo to Annapolis for an early morning conference. We stayed in the Maryland Inn, it was quaint, very clean, and cute. We really enjoyed the property, its location to the water and the conference. We'd definitely stay here again."

Hilton Garden Inn Annapolis Downtown

8/10 Good

"Room was awesome, very clean housekeeping staff extremely nice. Would suggest more help in the restaurant, food was excellent, poor waitress was running around trying to serve everyone!"

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"all good. Very good when it comes to parking during a boat show."

St Michaels Inn

10/10 Excellent

"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help in a variety of ways, local auto shop, contact with a driver, fresh coffee, etc."

Microtel Inn & Suites by Wyndham Gambrills/Odenton

10/10 Excellent

"The hotel is well maintained and looks modern. Our room is clean and spacious. It has all the amenities I need, particularly microwave and refrigerator. It has a complimentary continental breakfast as well, basic and has limited options. What I like most of this hotel is the location! We are so near to a lot of restaurants, grocery store, department stores - I love my Target and Ross, and even movie theater. All in all, a great value hotel! We’ll definitely be staying here again in the future."

Sonesta ES Suites Annapolis

10/10 Excellent

"Shalinda was the most welcoming front desk staff i have ever encountered."

Baymont by Wyndham Easton

10/10 Excellent

"Staff who received us was very helpful and respectful. Breakfast was great, rooms are well maintained and clean."

More cheap stays in Kent Island

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

1.865.719 ₫

2.070.948 ₫ total

26 Oct - 27 Oct

includes taxes & fees

7.2/10 Good! (509 reviews)

St Michaels Inn

1228 S Talbot Street St. Michaels MD

2.075.872 ₫

2.283.459 ₫ total

1 Nov - 2 Nov

includes taxes & fees

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

Best Western Annapolis

2520 Riva Rd Annapolis MD

2.053.814 ₫

2.341.348 ₫ total

20 Oct - 21 Oct

includes taxes & fees

7.8/10 Good! (1,008 reviews)

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

2.329.330 ₫

2.585.556 ₫ total

8 Nov - 9 Nov

includes taxes & fees

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

Microtel Inn & Suites by Wyndham Gambrills/Odenton

2525 Evergreen Rd. Gambrills MD

2.313.003 ₫

2.636.823 ₫ total

3 Nov - 4 Nov

includes taxes & fees

9.2/10 Wonderful! (1,158 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

2.617.516 ₫

2.983.968 ₫ total

18 Oct - 19 Oct

includes taxes & fees

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

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Book Hotels in Kent Island on Expedia.com

Find hotels in Kent Island, MD from 2.070.948 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Kent Island

Check prices for these dates

Filter by

Star rating

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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. Historic Inns of Annapolis

11. Crowne Plaza Annapolis by IHG

12. Inn at Perry Cabin

13. Graduate by Hilton Annapolis

14. Annapolis Waterfront Hotel, Autograph Collection

15. The Wildset

16. Holiday Inn Express & Suites Annapolis by IHG

17. Hilton Garden Inn Annapolis Downtown

18. SpringHill Suites by Marriott Annapolis

19. St Michaels Inn

20. Rod 'N' Reel Resort

Stay near popular Kent Island attractions

Matapeake State Park

Paul Reed Smith Guitars

Learn more about Kent Island

Top Kent Island Hotel Reviews

Crowne Plaza Annapolis by IHG

Best Western Annapolis

Historic Inns of Annapolis

Hilton Garden Inn Annapolis Downtown

Annapolis Waterfront Hotel, Autograph Collection

St Michaels Inn

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Sonesta ES Suites Annapolis

Baymont by Wyndham Easton

More cheap stays in Kent Island

Red Roof Inn & Suites Chestertown

St Michaels Inn

Best Western Annapolis

Best Western Kent Narrows Inn

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Holiday Inn Express & Suites Annapolis by IHG

Explore a world of travel with Expedia

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