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

Historic Hotels & Resorts in Kent Island

  • 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

Check availability on Kent Island Historic Hotels

Tonight
24 Sept - 25 Sept
Tomorrow
25 Sept - 26 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Kent Island historic hotels

1. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
United States
barbara s.
AU$1,830
includes taxes & fees
27 Sept - 28 Sept
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

2. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
United States
David R.
AU$2,004
includes taxes & fees
27 Sept - 28 Sept
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

3. Historic Inns of Annapolis

Historic Inns of Annapolis
Historic District
United States
ian
AU$221
includes taxes & fees
12 Oct - 13 Oct
Historic Inns of Annapolis

4. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Historic District
United States
Brian L.
AU$871
includes taxes & fees
28 Sept - 29 Sept
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

5. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
AU$604
includes taxes & fees
5 Oct - 6 Oct
Cozy 2br home w/ parking in downtown Annapolis

6. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
United States
Buu T.
AU$945
includes taxes & fees
29 Sept - 30 Sept
Chesapeake Cottages- 2 Quaint Waterfront Retreats
View all properties

Top Kent Island Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"I love the Graduate Hotel and it is very convenient. But please fix the parking garage gate 😬! It’s terrible!"
Jesse 4-night trip
Posted 12 hours ago
Graduate by Hilton Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"We were comfortable, very comfortable actually and this hotel had everything we needed to get our son off to college."
Joanna 2-night trip
Posted 19 hours ago
DoubleTree by Hilton Hotel Annapolis
Kent Island Resort

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."
Steven 2-night trip
Posted 2 days ago
Kent Island Resort
Annapolis Waterfront Hotel, Autograph Collection

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."
Karen 3-night trip
Posted 2 days ago
Annapolis Waterfront Hotel, Autograph Collection
Best Western Annapolis

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."
William 1-night trip
Posted 3 days ago
Best Western Annapolis
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 3 days ago
The Westin Annapolis
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"I thought breakfast was included but apparently not . There was not even complimentary coffee"
Gerald 2-night trip
Posted 3 days ago
Courtyard by Marriott Annapolis

Explore a world of travel with Expedia