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Top Kent Island hotels

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Stevensville MD
This vacation home features a garden, laundry facilities, and barbecue grills.
This was our second time spending Thanksgiving week at Woodland Retreat. We appreciate the overall cleanliness of the house. All the beds are very comfortable. The kitchen is well stocked. The primary suite has plenty of room for baby’s portable crib. The downstairs bonus room is ideal for family ...

Reviewed on Nov 30, 2025

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Opens in a new windowWoodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
240' Private Beachfront @Kent Island Love Point - Great for Families

240' Private Beachfront @Kent Island Love Point - Great for Families

stevensville MD
This vacation home features a garden, laundry facilities, and barbecue grills.
My friends and I absolutely loved our stay here. Hal was very responsive and made the check in and out as smooth as possible. He was available for any questions we had and made sure we had the best trip possible. 15 of us and 1 dog stayed here very comfortably, we would definitely return :)

Reviewed on Jan 5, 2026

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Opens in a new window240' Private Beachfront @Kent Island Love Point - Great for Families
Chesapeake Houseboat Getaway on Kent Island, Maryland

Chesapeake Houseboat Getaway on Kent Island, Maryland

Stevensville MD
This houseboat features barbecue grills.
5 stars

Reviewed on Feb 23, 2026

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Opens in a new windowChesapeake Houseboat Getaway on Kent Island, Maryland
Circa 1700 Chesapeake Colonial home on the National Register.

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville MD
An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Our family was in Stevensville for my nephew's wedding. When I saw this property on VRBO, I had to rent it. We had a special time here! Kyaking, canoeing, relaxing and swimming in the pool. This property is extraordinary with a novel vibe. Lots of outdoor space to hang out & explore (picnic tables, ...

Reviewed on Sep 25, 2025

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Opens in a new windowCirca 1700 Chesapeake Colonial home on the National Register.
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

4 out of 5
180 Pier One Road Stevensville MD
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $210 total per night from Mar 10 to Mar 11
$210 total
Mar 10 - Mar 11
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this traditional hotel. Traveling on business? Take advantage of the 24-hour business ...
Amazing. Clean. Beautiful.

Reviewed on Mar 2, 2026

Opens in a new windowThe Inn at Chesapeake Bay Beach Club
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $188 total per night from Mar 29 to Mar 30
$188 total
Mar 29 - Mar 30
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, ...
Lovely and fun theme hotel. Staff was wonderdul

Reviewed on Mar 8, 2026

Opens in a new windowGraduate by Hilton Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $179 total per night from Apr 2 to Apr 3
$179 total
Apr 2 - Apr 3
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. ...
Very clean, great staff, very good communication skills, excellent service, AC could have been turned on sooner, friendly. I just wish they had a restaurant on the premises.

Reviewed on Mar 9, 2026

Opens in a new windowHistoric Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
$110 nightly
The price is $125 total per night from Mar 13 to Mar 14
$125 total
Mar 13 - Mar 14
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
So clean and smells so fresh! Great hot shower. Really clean and comfortable bed. Worth the money

Reviewed on Mar 6, 2026

Opens in a new windowCrowne Plaza Annapolis by IHG
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street Annapolis MD
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $108 total per night from Apr 5 to Apr 6
$108 total
Apr 5 - Apr 6
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and ...
The staff were very friendly and helpful. The King Room was nice and clean. Located in a nice area. The drinks and food at the bar were nice. The only downside was the parking. The lot is small luckily I have a small car but once you’re parked you’re hesitant to leave because there may not be a space ...

Reviewed on Mar 8, 2026

Opens in a new windowHilton Garden Inn Annapolis Downtown
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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.

Frequently asked questions

What are the top kid-friendly hotels in Kent Island?
Take some of the trials out of traveling with young ones by opting for a family-friendly Kent Island hotel. From useful amenities to extra-helpful services, these properties feature perks that'll make your trip run smoothly: Settle in at ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️. It comes with a king bed, clothes washing facilities and a knack for making families feel at home. Otherwise, spend your nights in Kent Island at LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12. Take advantage of a king bed, pet-friendly facilities and more here.
Where can I find cheap hotels in Kent Island?
At Travelocity you'll find really nice hotels in Kent Island at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Kent Island rather than in Kent Island. We may find you even better rates, too.
How do I find the best Kent Island hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Kent Island then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Kent Island?
The cheapest hotel in Kent Island is $108. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Kent Island?
There are 1,297 hotels in Kent Island on Travelocity.
What are the best hotels in Kent Island?
Kent Island has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Kent Island for you!
When is the best time to visit Kent Island?
If you want the joy of a fun-filled trip in peak season, visit Kent Island during May, June and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as January, October and December.
When is the cheapest time to stay in Kent Island?
Based on historic data is usually the cheapest month to visit Kent Island. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Kent Island?
There are multiple hotels in Kent Island that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Kent Island. We have plenty of kid-friendly hotels in Kent Island to choose from on Travelocity!
Why book a hotel in Kent Island through Travelocity?
Because we have the top hotels in Kent Island! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Kent Island on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Kent Island hotel reviews by fellow wanderers

Historic Inns of Annapolis

Historic Inns of Annapolis

5 out of 5
Posted 13 hours ago
Travelocity Verified Review
"Very clean, great staff, very good communication skills, excellent service, AC could have been turned on sooner, friendly. I just wish they had a restaurant on the premises."
A verified traveler stayed at Historic Inns of Annapolis
Historic Inns of Annapolis

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