Kent Island Holiday Rentals, Maryland: Private House Rentals

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Kent Island

Pet friendly

Apartment

Pool

Spa

Condo

Hot tub

Family friendly

Cottage

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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

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

฿6,862

฿8,472 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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 bedroom with a large bed, a bench, a dresser, and two windows with curtains.

2. Kent Island Resort

Stevensville

Bethany

฿4,101

฿5,660 total

includes taxes & fees

11 Nov - 12 Nov

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

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

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.

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

Grasonville

Marc

฿3,318

฿3,683 total

includes taxes & fees

15 Nov - 16 Nov

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.

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

฿5,113

฿5,675 total

includes taxes & fees

25 Oct - 26 Oct

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

฿4,919

฿5,460 total

includes taxes & fees

9 Nov - 10 Nov

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

฿3,012

฿3,344 total

includes taxes & fees

9 Nov - 10 Nov

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

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

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

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

฿2,835

฿3,147 total

includes taxes & fees

15 Nov - 16 Nov

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

A marina with multiple boats docked during sunset.

8. Historic Inns of Annapolis

Historic District

Jennifer

฿2,872

฿4,420 total

includes taxes & fees

15 Nov - 16 Nov

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

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

A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.

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

9. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

฿3,558

฿4,056 total

includes taxes & fees

18 Oct - 19 Oct

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

10. The Westin Annapolis

Annapolis

Bobbi

฿6,669

฿7,603 total

includes taxes & fees

29 Oct - 30 Oct

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

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.

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

11. Crowne Plaza Annapolis by IHG

Annapolis

Jose

฿3,687

฿4,203 total

includes taxes & fees

15 Nov - 16 Nov

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

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.

12. Graduate by Hilton Annapolis

Annapolis

Mark

฿4,937

฿5,628 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 property with a docked boat, a tall building with balconies, and a church spire in the background.

13. Annapolis Waterfront Hotel, Autograph Collection

Historic District

William

฿7,481

฿8,528 total

includes taxes & fees

2 Nov - 3 Nov

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

14. SpringHill Suites by Marriott Annapolis

Annapolis

Kaiya

฿3,988

฿4,547 total

includes taxes & fees

9 Nov - 10 Nov

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 modern office setup with two monitors, a keyboard, and two wooden chairs.

15. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Omer

฿3,184

฿3,630 total

includes taxes & fees

15 Nov - 16 Nov

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

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.

A golf course with a water hazard and surrounding trees.

16. Inn at Perry Cabin

Downtown St. Michaels

Virgilio

฿17,796

฿19,576 total

includes taxes & fees

3 Nov - 4 Nov

17. Hilton Garden Inn Annapolis Downtown

Annapolis

petra

฿3,545

฿4,042 total

includes taxes & fees

10 Nov - 11 Nov

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

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.

A dark wooden panel wall with a mounted flat-screen TV, a bench with cushions, and a small plant in a vase.

18. The Wildset

Downtown St. Michaels

Sarah

฿7,675

฿9,280 total

includes taxes & fees

3 Nov - 4 Nov

A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

A hotel room with a large bed, a bedside table with a lamp, a phone, a mirror, and a bathroom with a bathtub and toilet.

A swimming pool with a tiled edge, wooden chairs, and tables around it.

A spacious dining area with multiple tables and chairs, a central bar area, and large windows providing natural light.

19. Country Inn & Suites by Radisson, Annapolis, MD

Annapolis

Catherine

฿3,057

฿3,484 total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

A gym with treadmills, weight machines, and dumbbells.

A modern lobby with a reception desk, seating area, and a patterned rug.

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

20. Sonesta ES Suites Annapolis

Edgewater

Dennis

฿3,184

฿3,630 total

includes taxes & fees

8 Nov - 9 Nov

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"The staff was awesome. Very professional and helpful. Our room was cleaned and well maintained. The food was great and the spa service was awesome as well."

Rod 'N' Reel Resort

10/10 Excellent

"Great rooom, really great service."

Microtel Inn & Suites by Wyndham Gambrills/Odenton

10/10 Excellent

"Clean, we'll maintained. Staffers friendly but professional A great stay"

Historic Inns of Annapolis

10/10 Excellent

"The convenience to downtown was the biggest plus for me. The Maryland Inn is on Main street so shopping and dining are an easy walk. I was in town for the Annapolis boat show so walking to and from the show was a fairly easy commute. The hotel was very clean, my room was well maintained each day. The only issue I had was the TV was not working but upon notification, it was fixed right away. Otherwise I'd say the only other thing that visitors will be surprised with is Check in is located at another hotel (all tied to same company), so there is a short walk to this property if you are getting dropped off. Overall impression - This is an OLD historic building and hotel - actually a meeting spot for the Annapolis Ghost Tours :-). So set your expectations for that, it is not an upscale, modern resort hotel experience. For me, it was perfect, and much better than some of the rental houses I've stayed in over the years. If you're excited about historic places and buildings, this will be a great experience for you."

Graduate by Hilton Annapolis

10/10 Excellent

"Good"

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent

"Perfect place to stay! Classy. Clean comfortable amazing staff"

Best Western Annapolis

8/10 Good

"Noisy balcony"

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!"

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."

More cheap stays in Kent Island

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

฿2,413

฿2,678 total

10 Nov - 11 Nov

includes taxes & fees

7.2/10 Good! (510 reviews)

Best Western Annapolis

2520 Riva Rd Annapolis MD

฿2,534

฿2,888 total

15 Nov - 16 Nov

includes taxes & fees

St Michaels Inn

1228 S Talbot Street St. Michaels MD

฿2,685

฿2,953 total

15 Nov - 16 Nov

includes taxes & fees

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

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

฿3,012

฿3,344 total

9 Nov - 10 Nov

includes taxes & fees

Microtel Inn & Suites by Wyndham Gambrills/Odenton

2525 Evergreen Rd. Gambrills MD

฿2,973

฿3,390 total

3 Nov - 4 Nov

includes taxes & fees

9.2/10 Wonderful! (1,152 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

฿3,184

฿3,630 total

15 Nov - 16 Nov

includes taxes & fees

Explore a world of travel with Expedia

More ways to book

Book Hotels in Kent Island on Expedia.com

Find hotels in Kent Island, MD from ฿2,678

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Kent Island

Check prices for these dates

Filter by

Star rating

Guest rating

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. Historic Inns of Annapolis

9. DoubleTree by Hilton Hotel Annapolis

10. The Westin Annapolis

11. Crowne Plaza Annapolis by IHG

12. Graduate by Hilton Annapolis

13. Annapolis Waterfront Hotel, Autograph Collection

14. SpringHill Suites by Marriott Annapolis

15. Holiday Inn Express & Suites Annapolis by IHG

16. Inn at Perry Cabin

17. Hilton Garden Inn Annapolis Downtown

18. The Wildset

19. Country Inn & Suites by Radisson, Annapolis, MD

20. Sonesta ES Suites Annapolis

Stay near popular Kent Island attractions

Matapeake State Park

Paul Reed Smith Guitars

Learn more about Kent Island

Top Kent Island Hotel Reviews

The Inn at Chesapeake Bay Beach Club

Rod 'N' Reel Resort

Microtel Inn & Suites by Wyndham Gambrills/Odenton

Historic Inns of Annapolis

Graduate by Hilton Annapolis

Annapolis Waterfront Hotel, Autograph Collection

Best Western Annapolis

Hilton Garden Inn Annapolis Downtown

St Michaels Inn

More cheap stays in Kent Island

Red Roof Inn & Suites Chestertown

Best Western Annapolis

St Michaels Inn

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

Go further with the Expedia app