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Hotels with connecting rooms in Kent Island

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Check availability on Kent Island Hotels with connecting rooms

Our top choices for Kent Island hotels with connecting rooms

Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (933)
"It was very comfortable and clean"
United States
Maria
The price is S$125
includes taxes & fees
3 Jan - 4 Jan, 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
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 S$146
includes taxes & fees
15 Dec - 16 Dec
The Lodge at Great Oak Landing
Exterior
Quality Inn

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (825)
"Everything was clean; staff friendly; breakfast great"
United States
Richard
The price is S$115
includes taxes & fees
21 Dec - 22 Dec
Quality Inn
Hypo-allergenic bedding, desk, blackout curtains, iron/ironing board
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1003)
"Cookies and coffee at check in .excellent staff "
United States
Cheryl
The price is S$140
includes taxes & fees
4 Jan - 5 Jan, 2026
Country Inn & Suites by Radisson, Annapolis, MD
Terrace/patio
The Tidewater Inn

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (842)
"Friendly staff, spotless room, great location. "
United States
Steven
The price is S$254
includes taxes & fees
1 Jan - 2 Jan, 2026
The Tidewater Inn
Exterior
Hampton Inn Easton

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (553)
"all excellent with kudos to staff and the breakfast cook."
United States
JOSEPH
The price is S$164
includes taxes & fees
8 Jan - 9 Jan, 2026
Hampton Inn Easton
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, (1006)
"Great place!"
United States
Tawnya
The price is S$112
includes taxes & fees
28 Dec - 29 Dec
DoubleTree by Hilton Hotel 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, (1008)
"Great value for stay with breakfast included "
United States
Aisling
The price is S$117
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Annapolis Downtown
Lobby
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1001)
"Spacious room, friendly staff, nice bathroom. Everyone is very accommodating."
United States
DONNA
The price is S$183
includes taxes & fees
15 Dec - 16 Dec
Best Western Plus Easton Inn & Suites
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1002)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
The price is S$120
includes taxes & fees
22 Dec - 23 Dec
Best Western Kent Narrows 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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Clean upscale rooom..bed was amazing "
Theo 1-night trip
Posted 5 days ago
DoubleTree by Hilton Hotel Annapolis

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Frequently asked questions

What are the best hotels with connecting rooms in Kent Island?
There are multiple hotels with connecting rooms in Kent Island with a total average guest review rating of 8.5, so you'll easily find a place that's right for you. If you're planning a trip to Chester, look into The Inn at Chesapeake Bay Beach Club. This popular 4-star hotel comes with connecting rooms, a terrace and pillow top mattresses. Another highly recommended option is Holiday Inn Express Annapolis - Kent Island, an IHG Hotel. This 2.5-star Chester getaway offers a terrace and a garden.
Why book your hotel with connecting rooms in Kent Island with Expedia?
Expedia makes it a breeze to find your ideal hotel with connecting rooms in Kent Island. Getting away with the family? Make the most of our filters to search for stays with perks like a pool. If you need to stick to a budget, click on how much you're willing to spend and the preferred star rating of your hotel. We'll help you find a suitable stay whatever your holiday looks like.
How can I find cheap hotels with connecting rooms in Kent Island?
Expedia is here to help you narrow down your search for cheap hotels with connecting rooms in Kent Island. To discover your perfect stay in a few quick keystrokes, simply use our convenient filter tool to refine your search results by budget, amenities and star rating.