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 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.

1. Kent Island Resort

Stevensville

Bethany

Rp2.732.198

Rp3.636.455 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 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.

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

2. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

Rp3.413.239

Rp4.242.767 total

includes taxes & fees

19 Oct - 20 Oct

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.

An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.

3. Best Western Kent Narrows Inn

Grasonville

Joshua

Rp2.076.142

Rp2.304.519 total

includes taxes & fees

29 Sept - 30 Sept

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.

4. DoubleTree by Hilton Hotel Annapolis

Annapolis

Michele

Rp1.480.283

Rp1.687.523 total

includes taxes & fees

27 Sept - 28 Sept

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

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.

5. St Michaels Inn

St. Michaels

Lynn

Rp1.686.541

Rp1.855.195 total

includes taxes & fees

24 Sept - 25 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

Rp1.590.346

Rp1.749.381 total

includes taxes & fees

29 Sept - 30 Sept

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

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

A hotel pool area with multiple pools, lounge chairs, and a pool lift.

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

7. Best Western Plus Easton Inn & Suites

Easton

Raheem

Rp2.302.263

Rp2.532.489 total

includes taxes & fees

27 Sept - 28 Sept

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.

8. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

Rp2.712.744

Rp3.011.145 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

9. Comfort Inn & Suites Chestertown

Chestertown

Amy

Rp1.913.198

Rp2.123.649 total

includes taxes & fees

13 Oct - 14 Oct

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 patio area with a stone fire pit, outdoor furniture, and a covered seating area.

10. Sonesta ES Suites Annapolis

Edgewater

Philip

Rp1.729.374

Rp1.971.487 total

includes taxes & fees

24 Sept - 25 Sept

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

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

11. Fairfield Inn & Suites by Marriott Easton

Easton

Amanda

Rp2.412.022

Rp2.653.225 total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

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.

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

Grasonville

Marc

Rp2.038.776

Rp2.263.041 total

includes taxes & fees

18 Oct - 19 Oct

A modern hotel kitchen with a central island, seating area, and various kitchen appliances.

A gym with treadmills, elliptical machines, and exercise balls.

A Best Western hotel with a modern facade, entrance with glass doors, and a parking area.

A hotel lobby with a reception desk, seating area, and dining space.

13. Best Western Annapolis

Annapolis

Sanaul

Rp1.333.349

Rp1.520.018 total

includes taxes & fees

27 Sept - 28 Sept

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

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.

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

14. The Tidewater Inn

Easton

Miriam

Rp3.551.553

Rp3.906.709 total

includes taxes & fees

29 Sept - 30 Sept

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

15. Quality Inn Grasonville near Kent Island

Grasonville

John

Rp1.784.700

Rp1.981.017 total

includes taxes & fees

13 Oct - 14 Oct

A modern lobby with a reception desk, seating area, and potted plants.

A modern hotel lobby with a sectional sofa, ottomans, round tables, potted plants, and a large window.

A modern bar area with a wooden counter, bar stools, and a wine display.

A Hilton Garden Inn with a large building and a smaller entrance building.

16. Hilton Garden Inn Annapolis

Annapolis

Glenn

Rp1.668.338

Rp1.901.905 total

includes taxes & fees

29 Sept - 30 Sept

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

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.

A marina with multiple boats docked during sunset.

17. Historic Inns of Annapolis

Historic District

ian

Rp1.897.761

Rp2.773.815 total

includes taxes & fees

12 Oct - 13 Oct

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

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

A hotel room with a bed, bedside tables, a desk with a chair, a microwave, a refrigerator, and a window with curtains.

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

18. Microtel Inn & Suites by Wyndham Gambrills/Odenton

Gambrills

Arlaan

Rp1.641.751

Rp1.871.596 total

includes taxes & fees

12 Oct - 13 Oct

A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.

A hotel room with a bed, a desk with a TV, a sofa with a red pillow, and a window with curtains.

A gym with treadmills, elliptical machines, a bench, and a rack of dumbbells.

A modern hotel kitchen with a buffet setup, including a waffle maker, coffee station, and various food containers.

19. Hampton Inn & Suites Annapolis

Annapolis

Earnest

Rp1.755.966

Rp2.001.801 total

includes taxes & fees

30 Sept - 1 Oct

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

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.

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

20. SpringHill Suites by Marriott Annapolis

Annapolis

FRANK

Rp2.307.036

Rp2.630.021 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.

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

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."

Hilton Garden Inn Annapolis Downtown

10/10 Excellent

"The restaurant inside the hotel is a great idea. but the variety of food is very limited. But it is just my opinion."

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good

"The view from our room was incredible. The property is clean and the beds comfortable. For the price, however, the only thing that justifies it is the view and location. There are 2 restaurants- Marmo was disappointing and overpriced. The cantina was great. Unfortunately, they take up all of the waterfront dock area, so there is really nowhere else to gather in the hotel to enjoy the water if you just want to sit and visit or play a game, or some such. (The balconies were too small for anything except a cup of coffee). And since the restaurants are open to the public the area is packed all the time. Otherwise, being an older hotel, there really aren't any special amenities. No spa or pool. nothing else special about it. And those terrible nespresso machines in the room. I just want a regular cup of coffee. Parking is overpriced- we hoofed it to a garage a few blocks away for significantly less per day."

Crowne Plaza Annapolis by IHG

10/10 Excellent

"U"

DoubleTree by Hilton Hotel Annapolis

8/10 Good

"The property is located in an awesome location; convenient to shopping and restaurants. They do have a decent bar and restaurant in the hotel. The property was clean, parking was free and available, staff was great. We would definitely stay again."

Holiday Inn Express & Suites Annapolis by IHG

10/10 Excellent

"Great"

Best Western Annapolis

10/10 Excellent

"The room was clean and well maintained. The lobby was pleasant, and the staff was friendly and attentive. The breakfast was excellent for this price point, with a wide selection of hot and cold items."

The Westin Annapolis

10/10 Excellent

"Only used the valet parking."

Courtyard by Marriott Annapolis

10/10 Excellent

"I thought breakfast was included but apparently not . There was not even complimentary coffee"

More cheap stays in Kent Island

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

Rp1.284.824

Rp1.426.155 total

29 Sept - 30 Sept

includes taxes & fees

7.2/10 Good! (496 reviews)

Best Western Annapolis

2520 Riva Rd Annapolis MD

Rp1.333.349

Rp1.520.018 total

27 Sept - 28 Sept

includes taxes & fees

7.8/10 Good! (1,006 reviews)

St Michaels Inn

1228 S Talbot Street St. Michaels MD

Rp1.686.541

Rp1.855.195 total

24 Sept - 25 Sept

includes taxes & fees

8/10 Very good! (1,001 reviews)

Microtel Inn & Suites by Wyndham Gambrills

2525 Evergreen Rd. Gambrills MD

Rp1.763.362

Rp2.010.232 total

19 Oct - 20 Oct

includes taxes & fees

9.2/10 Wonderful! (1,154 reviews)

Holiday Inn Express & Suites Annapolis by IHG

2451 Riva Rd Annapolis MD

Rp1.802.547

Rp2.054.904 total

29 Sept - 30 Sept

includes taxes & fees

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

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

Rp2.076.142

Rp2.304.519 total

29 Sept - 30 Sept

includes taxes & fees

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

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Book Hotels in Kent Island on Expedia.com

Find hotels in Kent Island, MD from Rp1.426.155

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. Kent Island Resort

2. The Inn at Chesapeake Bay Beach Club

3. Best Western Kent Narrows Inn

4. DoubleTree by Hilton Hotel Annapolis

5. St Michaels Inn

6. Baymont by Wyndham Easton

7. Best Western Plus Easton Inn & Suites

8. Hyatt Place Kent Narrows & Marina

9. Comfort Inn & Suites Chestertown

10. Sonesta ES Suites Annapolis

11. Fairfield Inn & Suites by Marriott Easton

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

13. Best Western Annapolis

14. The Tidewater Inn

15. Quality Inn Grasonville near Kent Island

16. Hilton Garden Inn Annapolis

17. Historic Inns of Annapolis

18. Microtel Inn & Suites by Wyndham Gambrills/Odenton

19. Hampton Inn & Suites Annapolis

20. SpringHill Suites by Marriott Annapolis

Stay near popular Kent Island attractions

Matapeake State Park

Paul Reed Smith Guitars

Learn more about Kent Island

Top Kent Island Hotel Reviews

Kent Island Resort

Hilton Garden Inn Annapolis Downtown

Annapolis Waterfront Hotel, Autograph Collection

Crowne Plaza Annapolis by IHG

DoubleTree by Hilton Hotel Annapolis

Holiday Inn Express & Suites Annapolis by IHG

Best Western Annapolis

The Westin 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

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