Kent Island Holidays from £617
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Your Kent Island Holiday
Travel on your own terms with an Kent Island holiday package. Whether you're off to Chester to experience its watersports, history and culture, or someplace else, our package deals make travel planning easy. With so much to see and do on a trip to Kent Island, it can be difficult to know where to begin. Kick off your travels in Chester at Chesapeake Bay Bridge and Sandy Point Beach — two leading attractions here. Another great city to add to your itinerary is Romancoke. Don't miss St. Michaels Winery and Chesapeake Bay Maritime Museum. Expedia is a one-stop shop for organising your Kent Island holiday. From flights and hotels, to activities and more, we know how to curate a travel experience like no other.
Top Kent Island Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Kent Island Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Baltimore Washington Intl. Thurgood Marshall Airport (BWI) |
Top hotels in Kent Island
The Inn at Chesapeake Bay Beach Club
180 Pier One Road Stevensville MD
Fully refundableReserve now, pay when you stay
£176
28 Sept - 29 Sept
includes taxes & fees
Kent Island Resort
500 Kent Manor Dr Stevensville MD
£141
14 Oct - 15 Oct
includes taxes & fees
9.2/10 Wonderful! (185 reviews)
"Just a wonderful place, we had an amazing stay!"
Reviewed on 6 Sept 2026
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Stevensville MD
10/10 Exceptional! (217 reviews)
"The place was great"
Reviewed on 29 Aug 2026
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.
Stay near popular Kent Island attractions
Matapeake State Park
7.6/10 (4 reviews)
Matapeake State Park features serene Chesapeake Bay views from its beach and trails. Enjoy panoramic Bay Bridge vistas while picnicking, or visit the separate dog-friendly beach area.
Paul Reed Smith Guitars
Witness master luthiers transform raw wood into world-class electric guitars at this renowned factory. The 90-minute guided tour reveals meticulous craftsmanship from wood selection to final assembly.
Frequently asked questions
How much does a Kent Island travel package cost?
The most affordable Kent Island travel package is £617, so your dream holiday can become a reality — without a hefty price tag. Combine flights, hotels, car rentals and more to create a package that matches your travelling style.
If I'm not able to travel, can I cancel my Kent Island travel package?
Whether it's your hotel, flight or rental car, you can cancel and rebook it. Booked your Kent Island travel package in the last 24 hours? You may be able to make changes for free. For bookings made more than 24 hours ago, you may incur a charge from your airline, hotel or car rental company. For more information, look up our Customer Service Portal. We'll help you every step of the way.
How do I get a cheap travel package to Kent Island?
Browse and lock in everything all in one place with our Kent Island holiday packages. You'll find deals on flights, hotels and more that'll keep your bank account happy and your sense of adventure alive. And, with more than 550 airlines and 1,000,000 hotel options globally to choose from, you have countless opportunities to mix and match as you please.
Does Expedia offer Book Now, Pay Later Kent Island holidays?
We do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply click on the payment plan that works for you during the checkout process and take away the stress of budgeting for your next trip. Be sure to bundle your flights, accommodation and activities with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:
- Pay monthly holidays: Escape on that dream holiday sooner with Klarna's convenient monthly instalment plans. If paying just a small amount each month sounds right for you, pick this option during the checkout process.
- Pay in instalments holidays: If you'd prefer to pay for your escape in multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: If paying a small percentage of your trip (rather than all of it upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan with Klarna.
How far in advance should I book my Kent Island holiday?
Savvy travellers often book as early as possible. You can normally look up international fares on Expedia up to 12 months before your intended flight. If you're booking at the last minute, don't worry. Cheap prices sometimes occur in the last weeks before departure dates.
What does an Expedia Kent Island travel package include?
With Expedia, you can select any combination of car rentals, hotels and flights to build your ideal Kent Island package. Once you've made your booking, you can add on the fun things like tours and experiences. Don't forget — the more you bundle, the more you stand to save!
What should I know before booking a Kent Island travel package?
Our prices are already low. However, you'll snap up even more bargains if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll always get transparent pricing and loads of choice.
Can I choose my airline with a Kent Island Expedia travel package?
Expedia offers access to more than 550 airline partners globally, so you sure can! Simply select the carrier that suits you and create the perfect Kent Island holiday.
Explore a world of travel with Expedia
- Beach Resorts & in Annapolis
- Charming Pet
- Crowne Plaza Annapolis by IHG
- Downtown Nights on the Water - Classic Cruiser Getaway
- Hotels with Early Check-in in Annapolis
- Hotels with Indoor Pools in Annapolis
- Sonesta ES Suites Annapolis
- Spa Hotels in Annapolis
- The Inn at Chesapeake Bay Beach Club
- Kent Island Resort
- Waterfront 2
- Wright's Cottage
- Annapolis Hotels
- Villas in Chester
- Adults Only Resorts & in Maryland
- All-Inclusive Hotels in Maryland
- Beach Resorts & in Maryland
- Cheap Hotels in Maryland
- Casino Hotels in Maryland
- Maryland Hotels
- Waterfront Escape Near Annapolis
- Hilton Garden Inn Kent Island Marina
- Highland Beach Hotels
- Historic District Hotels
- Gay-Friendly Hotels in Hunt Meadows
- Pet-Friendly Hotels in Kent Island
- Caravan Parks in Maryland
- Hostels in Maryland
- Houseboats in Maryland
- Lodges in Maryland
- Hotels near Maryland Quiet Waters Park
- Gay-Friendly Hotels in Parole
- Lowes Wharf Marina Inn
- Minutes from Downtown St. Michael's
- Downtown St. Michaels
- St. Michaels Hotels
- Kent Island Waterfront
- Washington Hotels
- Flights to Annapolis
- Flights to Arnold
- Flights to Baltimore
- Flights to Kent Island
- Flights to St. Michaels
- Flights to Washington
- Flights to Maryland
- Flights from Maryland
- Flights from Barclay
- Flights from Queen Anne's County
- Flights from Houston (IAH) to Annapolis (ANP)
- Flights from New York (JFK) to Annapolis (ANP)
- Flights from London (LHR) to Annapolis (ANP)
- Flights from London (LHR) to Baltimore (BWI)
- Flights from Manchester (MAN) to Annapolis (ANP)
- Adelphi Holidays
- Annapolis Holidays
- Baltimore Museum of Art
- Baltimore Holidays
- Benjamin Banneker Historical Park & Museum
- Blackwater National Wildlife Refuge
- Breezy Point Beach
- Chesapeake Beach Holidays
- Choptank River Lighthouse
- Christ Episcopal Church
- Clinton Holidays
- Dorsey Holidays
- Ellicott City Holidays
- Greenbelt Holidays
- Hammond-Harwood House
- Harriet Tubman Underground Railroad National Historical Park
- Hippodrome Theatre
- Visit Kent Island
- Laurel Holidays
- All inclusive Holiday Packages Gibson Island
- Kid friendly Holiday Packages Maryland
- Marley Holidays
- Maryland Zoo
- Maryland Holidays
- Visit Maryland
- Mount Rainier Holidays
- National Aquarium in Baltimore
- Oriole Park at Camden Yards
- Port Discovery Childrens Museum
- Visit Shady Side
- Spocott Windmill
- U.s. Naval Academy
- Uss Constellation
- Washington Holidays
- Waterloo Holidays
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
