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Kent Island Hotels with Restaurants

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Check availability on Kent Island Hotels with Restaurants

Our top choices for Kent Island hotels with a restaurant

Front of property – evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (429)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
The price is RM755
RM942 total
includes taxes & fees
15 Dec - 16 Dec
The Inn at Chesapeake Bay Beach Club
Balcony
Rod 'N' Reel Resort

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very good, (1000)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is RM437
RM567 total
includes taxes & fees
2 Jan - 3 Jan 2026
Rod 'N' Reel Resort
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
The price is RM554
RM790 total
includes taxes & fees
1 Jan - 2 Jan 2026
Wylder Tilghman Island
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1003)
"Great place!"
United States
Tawnya
The price is RM313
RM357 total
includes taxes & fees
28 Dec - 29 Dec
DoubleTree by Hilton Hotel Annapolis
Private beach nearby, sun-loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
The price is RM406
RM465 total
includes taxes & fees
15 Dec - 16 Dec
The Lodge at Great Oak Landing
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1000)
"Excellent from check in to check out, highly recommend!"
United States
Eric
The price is RM530
RM604 total
includes taxes & fees
14 Dec - 15 Dec
Crowne Plaza Annapolis by IHG
Hypo-allergenic bedding, down duvets, in-room safe, desk
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1000)
"Clean room, fast and easy check in, made to order breakfast options. "
United States
Michael
The price is RM319
RM364 total
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Annapolis
Living area
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1007)
"Great value for stay with breakfast included "
United States
Aisling
The price is RM325
RM371 total
includes taxes & fees
23 Dec - 24 Dec
Hilton Garden Inn Annapolis Downtown
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (674)
"Great view, good ambiance all around"
United States
Dianne
The price is RM477
RM529 total
includes taxes & fees
14 Dec - 15 Dec
Hyatt Place Kent Narrows & Marina
Terrace/patio
The Tidewater Inn

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (841)
"Friendly staff, spotless room, great location. "
United States
Steven
The price is RM735
RM808 total
includes taxes & fees
14 Dec - 15 Dec
The Tidewater Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Kent Island Hotel Reviews

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Excellent from check in to check out, highly recommend!"
Eric 1-night trip
Posted 5 days ago
Crowne Plaza Annapolis by IHG

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Frequently asked questions

What are the best hotels with dining in Kent Island?
Kent Island offers multiple hotels with dining that have a total average guest review rating of 8.6. Eager to discover top dining experiences in Chester? Stay at The Inn at Chesapeake Bay Beach Club, a 4-star stay with pillow top mattresses and a sauna. Or, eat your way around the city from Hilton Garden Inn Kent Island. Also a traveller favourite, it has a 3-star rating and amenities such as an electric car charging station and pool sun loungers.
Why book your hotel with restaurants in Kent Island with Expedia?
With Expedia, you'll have no trouble finding your ideal hotel with restaurants in Kent Island. Find your way to the filters to search for properties with their own restaurants. If you have a budget in mind, select how much you're willing to spend and your preferred hotel star rating. We'll help you find the right place whatever your bank balance or tastes.
How can I find cheap hotels with restaurants in Kent Island?
With Expedia's handy filter tool, getting your hands on cheap hotels with restaurants in Kent Island is easy. To discover properties that are easy on the wallet, narrow your search results by budget, star rating and meal plans.