Kent Island, MD Villas from ₩95,739

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Recommended hotels in Kent Island

A large, multi-story building with a prominent red cylindrical tower, a covered patio area, and a well-maintained garden.

1. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

₩304,064 total

includes taxes & fees

Dec 9 - Dec 10

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

2. Kent Island Resort

Stevensville

Bethany

₩226,823 total

includes taxes & fees

Dec 10 - Dec 11

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

Grasonville

Michelle

₩150,666 total

includes taxes & fees

Nov 23 - Nov 24

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

4. Hyatt Place Kent Narrows & Marina

Grasonville

Michael

₩199,928 total

includes taxes & fees

Nov 25 - Nov 26

A multi-story hotel with a covered entrance and a flagpole.

5. Best Western Kent Narrows Inn

Grasonville

Holly

₩134,001 total

includes taxes & fees

Nov 25 - Nov 26

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

6. Hilton Garden Inn Kent Island Marina

Grasonville

Gamil

₩178,591 total

includes taxes & fees

Nov 18 - Nov 19

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

₩124,042 total

includes taxes & fees

Dec 1 - Dec 2

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

8. Historic Inns of Annapolis

Historic District

Christiaan

₩155,079 total

includes taxes & fees

Nov 23 - Nov 24

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

9. The Wildset

Downtown St. Michaels

Dena

₩327,595 total

includes taxes & fees

Dec 1 - Dec 2

A building with a covered porch supported by columns, a garage with a parked truck, and a small garden with flowers.

10. St Michaels Inn

St. Michaels

John

₩116,282 total

includes taxes & fees

Dec 3 - Dec 4

A building with a sign reading "The Inn."

11. Knapps Narrows Marina & Inn

Sherwood

Mary Ann

₩147,830 total

includes taxes & fees

Nov 12 - Nov 13

A waterfront property with a grassy lawn, white chairs, a dock, and a large building with multiple windows and a flag.

12. Inn at Perry Cabin

Downtown St. Michaels

Virgilio

₩643,317 total

includes taxes & fees

Dec 9 - Dec 10

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

13. Crowne Plaza Annapolis by IHG

Annapolis

Jose

₩157,802 total

includes taxes & fees

Dec 9 - Dec 10

14. Village Inn Annapolis MD

Annapolis

"very clean room. All the basic items you need from a budget motel. I admit on the outside the motel looks a bit rough, but inside the rooms where it really matters, it was clean, well organized, and comfortable. I would stay here again, if I was looking for a cheap accommodation in the Annapolis area. Despite being right next to a busy state highway, it was very quiet and conveniently located to a couple of local restaurants and a convenience store."

Keith

₩127,088 total

includes taxes & fees

Nov 16 - Nov 17

View all 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

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

Top reviews in Kent Island

Hyatt Place Kent Narrows & Marina

Grasonville

10/10 Excellent

Joe

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

10/10 Excellent

The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...

Christina

The Inn at Chesapeake Bay Beach Club

Stevensville

10/10 Excellent

Chuck

Hilton Garden Inn Kent Island Marina

Grasonville

10/10 Excellent

Kathie

Kent Island Resort

Stevensville

10/10 Excellent

I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.

John

Best Western Kent Narrows Inn

Grasonville

10/10 Excellent

Valerie

Inn at Perry Cabin

Downtown St. Michaels

10/10 Excellent

Norm

Historic Inns of Annapolis

Historic District

10/10 Excellent

Robert

Quality Inn Grasonville near Kent Island

Grasonville

10/10 Excellent

My wife and have been staying here off and on for a few years now. We have always found it to a lovely place stay . The staff there is especially courteous and helpful whenever a special need arises ! We give special notice of thanks to general manager Amy Patel for her attention to service and her pleasant attitude at all times ! Her caring manner and attention to detail are par excellence ! The cleanliness , breakfast included , location and the inground pool make this a sure bet for any...

Chuck

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

Fairfield Inn & Suites by Marriott Easton

Easton

10/10 Excellent

The Fairfield Inn on US50 has become our go-to mid-range hotel in Easton. We have stayed here several times in recent years, and once again had a great experience during this Christmas stay. The facilities are clean and in good condition. The staff is friendly, welcoming, and accommodating. When I booked our stay this time through a third-party, I got a little confused about room options, and took the only king-bed room that I saw. The manager didnt know I had any concerns, and when the staff...

Richard

A two-story white building with a central entrance, steps, and a pink door.

134 Prince - Luxury Boutique Hotel

Annapolis

10/10 Excellent

Reyna

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

SpringHill Suites by Marriott Annapolis

Annapolis

10/10 Excellent

Julie

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

DoubleTree by Hilton Hotel Annapolis

Annapolis

10/10 Excellent

Celina

A Country Inn & Suites by Radisson building with a brick facade, white columns, and a green roof.

Country Inn & Suites by Radisson, Annapolis, MD

Annapolis

10/10 Excellent

Anonymous traveler

Frequently Asked Questions

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Search Villas in Kent Island

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Recommended hotels in Kent Island

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. Best Western Kent Narrows Inn

6. Hilton Garden Inn Kent Island Marina

7. Quality Inn Grasonville near Kent Island

8. Historic Inns of Annapolis

9. The Wildset

10. St Michaels Inn

11. Knapps Narrows Marina & Inn

12. Inn at Perry Cabin

13. Crowne Plaza Annapolis by IHG

14. Village Inn Annapolis MD

Learn more about Kent Island

Top reviews in Kent Island

Hyatt Place Kent Narrows & Marina

10/10 Excellent

Frequently Asked Questions

Why book your villa in Kent Island with Expedia?

How can I find cheap villas in Kent Island?

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