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 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 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.

1. Kent Island Resort

Stevensville

Bethany

3.968.093 ₫

5.281.386 ₫ total

includes taxes & fees

12 Oct - 13 Oct

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

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.

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

2. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

4.957.200 ₫

6.161.897 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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

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

3. St Michaels Inn

St. Michaels

Will

2.449.440 ₫

2.694.384 ₫ total

includes taxes & fees

14 Sept - 15 Sept

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.

4. SpringHill Suites by Marriott Annapolis

Annapolis

Joshua

3.265.920 ₫

3.723.149 ₫ total

includes taxes & fees

14 Sept - 15 Sept

A lobby with a reception desk, a clock, and a wall-mounted deer head.

A laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.

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

5. Best Western Kent Narrows Inn

Grasonville

Joshua

3.015.274 ₫

3.346.953 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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

A kitchen with a stone wall, a microwave, and various food items on the counter.

A swimming pool with lounge chairs and umbrellas, surrounded by a fence and a building with columns.

A residential area with a large building, a swimming pool, and well-maintained lawns.

6. Baymont by Wyndham Easton

Easton

Erik

2.543.011 ₫

2.797.313 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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.

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

7. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

3.939.840 ₫

4.373.222 ₫ total

includes taxes & fees

4 Oct - 5 Oct

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.

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

Grasonville

jayne

3.084.480 ₫

3.423.773 ₫ total

includes taxes & fees

13 Oct - 14 Oct

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

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.

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

9. DoubleTree by Hilton Hotel Annapolis

Annapolis

Chereis

2.149.883 ₫

2.450.867 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A modern dining area with a central island, multiple tables, and chairs. There are signs for 'RISP' and 'SILVER' on the wall, and an 'EXIT' sign above a door.

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

A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

A modern lounge area with seating, a fireplace, and a television.

10. Comfort Inn & Suites Chestertown

Chestertown

Amy

2.694.643 ₫

2.991.053 ₫ total

includes taxes & fees

4 Oct - 5 Oct

A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

A hotel lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.

A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.

A hotel room with a sofa, armchair, and a small table. There is a lamp on a side table, and a door leading to another room.

11. Best Western Plus Easton Inn & Suites

Easton

Stephen

3.343.680 ₫

3.678.048 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

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

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.

12. Historic Inns of Annapolis

Historic District

Amy

2.562.932 ₫

3.808.207 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.

A hotel with a covered entrance, multiple floors, and a parking lot.

An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.

An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.

13. Fairfield Inn & Suites by Marriott Easton

Easton

Amanda

3.503.088 ₫

3.853.397 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.

A bedroom with a large bed, a nightstand, a lamp, and a window with blinds.

A spacious dining area with multiple tables and chairs, wooden ceiling beams, and large windows with blinds.

A spacious living room with a leather sofa, a coffee table, and a bookshelf filled with books.

14. The Tidewater Inn

Easton

Miriam

4.898.880 ₫

5.388.768 ₫ total

includes taxes & fees

29 Sept - 30 Sept

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

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

15. Sonesta ES Suites Annapolis

Edgewater

Philip

2.514.240 ₫

2.866.233 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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

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

16. Quality Inn Grasonville near Kent Island

Grasonville

Faezeh

2.592.000 ₫

2.877.120 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A multi-story Microtel by Wyndham hotel with a parking lot and a landscaped area in front.

A modern hotel lobby with a sofa area, a flat-screen TV, and a dining area.

A snack and beverage vending area with various snacks and drinks.

A reception area with a modern design, featuring a reception desk, seating area with patterned ottomans, and a wall with a geometric pattern.

17. Microtel Inn & Suites by Wyndham Gambrills

Gambrills

Mark

2.533.680 ₫

2.888.395 ₫ total

includes taxes & fees

12 Oct - 13 Oct

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

A breakfast bar with labeled sections for cereal and fruit, a kettle, and condiments.

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.

18. Holiday Inn Express & Suites Annapolis by IHG

Annapolis

Harold

2.617.920 ₫

2.984.429 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

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

19. Crowne Plaza Annapolis by IHG

Annapolis

Cynthia

2.851.200 ₫

3.250.368 ₫ total

includes taxes & fees

27 Sept - 28 Sept

A modern living room with a large window, a dining area, and a kitchen in the background.

A modern hotel lobby with grey sofas, wooden accents, and a large TV on the wall.

A modern gym with weight racks, benches, and exercise equipment.

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

20. Candlewood Suites Annapolis by IHG

Annapolis

Javier

2.436.480 ₫

2.905.632 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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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

DoubleTree by Hilton Hotel Annapolis

8/10 Good

"Ask the room far from the highway side. The highway at the night is to noisy."

The Tidewater Inn

10/10 Excellent

"⭐️⭐️⭐️⭐️⭐️ Wonderful Birthday Getaway! We had a wonderful stay at The Tidewater Inn for my spouse’s birthday weekend. Our room was clean, spacious, comfortable, and perfect for a relaxing getaway. The location is one of the best parts of the property...you’re within walking distance of historic sites, great restaurants, shops, and trails, with several spa and wellness options nearby. We really enjoyed being able to park the car and explore downtown Easton on foot. The area has so much charm, and The Tidewater Inn puts you right in the center of it while still providing a peaceful place to relax at the end of the day. From enjoying room service in the morning to exploring the town and nearby restaurants, everything came together for a memorable weekend. We would absolutely stay here again and highly recommend The Tidewater Inn for a romantic weekend, birthday celebration, or relaxing Eastern Shore getaway! ❤️"

Historic Inns of Annapolis

8/10 Good

"Property was a historical renovation which is very well done. Best part was location. A bit pricey and we didn’t need or use the complimentary bottle of wine. Bottled water would have been preferred. Staff and housekeeping was great. Coffee was available, but no food service for breakfast."

St Michaels Inn

8/10 Good

"Well, it was a nice hotel and the price was reasonable, but it’s a little rundown the rooms inside a very nice, but the overall property is certainly not pretty. The other thing is it’s kind of a mix between nice and not so nice. Breakfast was less than average coffee was weak and not that good but again if you want to stay near Saint Michael’s and don’t have to travel in from Easton it’s a it’s an OK pick"

Graduate by Hilton Annapolis

10/10 Excellent

"Great stay- Go Navy Beat Army!"

Crowne Plaza Annapolis by IHG

10/10 Excellent

"All good."

Sonesta ES Suites Annapolis

10/10 Excellent

"great place good price"

Best Western Annapolis

8/10 Good

"Clean but no coffee maker in room. Limited breakfast that wasn’t very good. Would not stay here again."

Courtyard by Marriott Annapolis

8/10 Good

"Nice location to get to the Maryland REN Faire, Annapolis and multiple restaurants and shopping opportunities"

More cheap stays in Kent Island

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

1.866.007 ₫

2.071.268 ₫ total

20 Sept - 21 Sept

includes taxes & fees

7.2/10 Good! (489 reviews)

Best Western Annapolis

2520 Riva Rd Annapolis MD

1.959.552 ₫

2.233.890 ₫ total

27 Sept - 28 Sept

includes taxes & fees

7.8/10 Good! (1,002 reviews)

St Michaels Inn

1228 S Talbot Street St. Michaels MD

2.449.440 ₫

2.694.384 ₫ total

14 Sept - 15 Sept

includes taxes & fees

8/10 Very good! (1,012 reviews)

Microtel Inn & Suites by Wyndham Gambrills

2525 Evergreen Rd. Gambrills MD

2.533.680 ₫

2.888.395 ₫ total

12 Oct - 13 Oct

includes taxes & fees

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

2.617.920 ₫

2.984.429 ₫ total

27 Sept - 28 Sept

includes taxes & fees

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

3.015.274 ₫

3.346.953 ₫ total

28 Sept - 29 Sept

includes taxes & fees

Explore a world of travel with Expedia

Book Hotels in Kent Island on Expedia.com

Find hotels in Kent Island, MD from 2.071.268 ₫

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. Kent Island Resort

2. The Inn at Chesapeake Bay Beach Club

3. St Michaels Inn

4. SpringHill Suites by Marriott Annapolis

5. Best Western Kent Narrows Inn

6. Baymont by Wyndham Easton

7. Hyatt Place Kent Narrows & Marina

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

9. DoubleTree by Hilton Hotel Annapolis

10. Comfort Inn & Suites Chestertown

11. Best Western Plus Easton Inn & Suites

12. Historic Inns of Annapolis

13. Fairfield Inn & Suites by Marriott Easton

14. The Tidewater Inn

15. Sonesta ES Suites Annapolis

16. Quality Inn Grasonville near Kent Island

17. Microtel Inn & Suites by Wyndham Gambrills

18. Holiday Inn Express & Suites Annapolis by IHG

19. Crowne Plaza Annapolis by IHG

20. Candlewood Suites Annapolis by IHG

Stay near popular Kent Island attractions

Matapeake State Park

Paul Reed Smith Guitars

Learn more about Kent Island

Top Kent Island Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

The Tidewater Inn

Historic Inns of Annapolis

St Michaels Inn

Graduate by Hilton Annapolis

Crowne Plaza Annapolis by IHG

Sonesta ES Suites Annapolis

Best Western Annapolis

Courtyard by Marriott Annapolis

More cheap stays in Kent Island

Red Roof Inn & Suites Chestertown

Best Western Annapolis

St Michaels Inn

Microtel Inn & Suites by Wyndham Gambrills

Holiday Inn Express & Suites Annapolis by IHG

Best Western Kent Narrows Inn

Explore a world of travel with Expedia