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Find Hotels with Connecting Rooms in Kent Island, MD

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Check availability on Kent Island Hotels with Connecting Rooms

Our top choices for Kent Island hotels with connecting rooms

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
$113 nightly
The price is $126
Dec 15 - Dec 16
Total with taxes and fees
The Lodge at Great Oak Landing
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
$129 nightly
The price is $142
Dec 14 - Dec 15
Total with taxes and fees
Best Western Plus Easton Inn & Suites
Lobby
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, (1002)
"Clean hotel, solid breakfast, and great staff. Beds are comfortable and rooms are up to date and quiet."
United States
Paul
$95 nightly
The price is $109
Jan 4 - Jan 5, 2026
Total with taxes and fees
Country Inn & Suites by Radisson, Annapolis, MD
Reception
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
$76 nightly
The price is $87
Dec 28 - Dec 29
Total with taxes and fees
DoubleTree by Hilton Hotel Annapolis
Bar (on property)
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
$109 nightly
The price is $120
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hampton Inn Easton
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
$81 nightly
The price is $89
Dec 21 - Dec 22
Total with taxes and fees
Quality Inn
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, (932)
"It was very comfortable and clean"
United States
Maria
$87 nightly
The price is $97
Jan 3 - Jan 4, 2026
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
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
$121 nightly
The price is $138
Dec 21 - Dec 22
Total with taxes and fees
Crowne Plaza Annapolis by IHG
Indoor pool
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, (1000)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
$83 nightly
The price is $93
Dec 22 - Dec 23
Total with taxes and fees
Best Western Kent Narrows Inn
Exterior
Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.0 out of 10, Wonderful, (1001)
"Nice place to stay! Clean, friendly staff, close to restaurants,stores, and movies!"
United States
Valda
$74 nightly
The price is $85
Dec 22 - Dec 23
Total with taxes and fees
Microtel Inn & Suites by Wyndham Gambrills
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
"This is a very nice hotel clean and seems to be new"
richard 1-night trip
Posted 2 days ago
Crowne Plaza Annapolis by IHG

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 8.6, 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 vacation 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.

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