Chesapeake Beach Packages (Flight + Hotel)
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Chesapeake Beach Beach Holiday
Live out those beachy daydreams on your Chesapeake Beach holiday. Enjoy a relaxing stroll, marvel at the beautiful coastal vistas and collect pretty seashells during your trip to Chesapeake Beach. Just 8 kilometres from the town centre, Breezy Point Beach is the place to be for many sun-seeking travellers. Have a look through our Chesapeake Beach holiday deals and watch your travel budget stretch further!
Top hotels in Chesapeake Beach
Rod 'N' Reel Resort
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
฿4,779
฿6,405 total
7 Oct - 8 Oct
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
"Wanted some place nice, clean, and low key to take my 90 year young mom and it checked all the boxes. It was about 2hr drive from where she lives in DE. Having at least 4 - 5 places on site to get food was great. CVS, McDonalds, a supermarket was short distance to walk. Room was spacious, modern ..."
Reviewed on 12 Sept 2026
St Michaels Inn
1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
฿3,123
฿3,436 total
15 Sept - 16 Sept
includes taxes & fees
8/10 Very good! (1,012 reviews)
"Well, it was a nice hotel and the price was reasonable, but it’s a little rundown the rooms inside a very nice, but the overall property is certainly not pretty. The other thing is it’s kind of a mix between nice and not so nice. Breakfast was less than average coffee was weak and not that good but ..."
Reviewed on 12 Sept 2026
Sonesta ES Suites Annapolis
170 Admiral Cochrane Dr Edgewater MD
Fully refundableReserve now, pay when you stay
฿3,107
฿3,542 total
1 Oct - 2 Oct
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"great place good price"
Reviewed on 11 Sept 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 Chesapeake Beach attractions
Breezy Point Beach
8.4/10 (61 reviews)
Stroll this half-mile Chesapeake Bay shoreline where gentle waves meet fossil-hunting adventures. Relax in shaded picnic areas after swimming in the netted area or trying your luck at the 200-foot fishing pier.
Photo by Ronanne Vinson
Chesapeake Beach Water Park
8.2/10 (88 reviews)
This family-friendly water park offers water slides, a lazy river, and pools for all ages. Currently closed for renovations until 2027, it will reopen with modernised facilities and new attractions.
Rod n Reel Charter Fishing
7.6/10 (31 reviews)
Explore the waterfront in Chesapeake Beach with a trip to Rod n Reel Charter Fishing. Visit the spas in this relaxing area or simply enjoy its restaurants.
Chesapeake Beach Railway Museum
8.0/10 (34 reviews)
Housed in the original 1898 railway station, this museum chronicles Chesapeake Beach Resort's golden era. View authentic artefacts and a restored vintage railway car while exploring early 20th century coastal tourism.
Bruce Gabrielson's Surf Art Gallery and Museum
7.8/10 (19 reviews)
Maryland's only surfing museum showcases Bruce Gabrielson's 50-year collection of historic boards and rare artefacts. Visitors can arrange private tours to see Duke Kahanamoku exhibits and Dale Velzy's shaping equipment.
Brownies Beach
Why not spend a lazy afternoon at Brownies Beach during your trip to Chesapeake Beach? Stroll along this relaxing area's beaches or simply enjoy its restaurants.
What to do in Chesapeake Beach
Chesapeake Beach: Sunset Sailing Cruise with Snacks
฿3,739
per adult
Chesapeake Beach: Guided Walking Tour to The Cliffs
฿1,549
per adult
Frequently asked questions
How much does a Chesapeake Beach holiday package cost?
You can grab a holiday package to this destination on Expedia. But how much your holiday to Chesapeake Beach costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Chesapeake Beach?
If you'd like to score a cheap Chesapeake Beach holiday package, consider travelling in January, February and April. You're likely to find better prices on hotels and flights during these months — ideal for a budget-friendly getaway.
How many days is enough for Chesapeake Beach?
You can easily visit all the top attractions in Chesapeake Beach within a few days, including the must-see Bruce Gabrielson's Surf Art Gallery and Museum. If you're after a longer Chesapeake Beach holiday, look at which kind of excursions and activities are available in the area.
Is it worth booking a holiday package to Chesapeake Beach?
Chesapeake Beach has all the ingredients you need for an awesome break — family-friendly attractions, history and watersports are just the start. Whether you'd like to visit sights like Chesapeake Beach Water Park and Chesapeake Beach Railway Museum, or take the road less traveled, you'll find plenty to see and do on your Chesapeake Beach holiday.
How to find the best Chesapeake Beach package deals?
Use Expedia's filter tool to help you find some tempting Chesapeake Beach package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Chesapeake Beach package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book a Chesapeake Beach holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking flights and accommodation separately. Better still, you can personalise your Chesapeake Beach escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Chesapeake Beach?
Secure fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Chesapeake Beach trip.
How to plan a trip to Chesapeake Beach?
- Choose when to get away: Check your diary and get packing. Your preferred time of year and the type of activities on offer will also help you decide when to holiday in Chesapeake Beach.
- Budget wisely: As well as the price of your stay, you should factor in other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that could crop up during your trip to Chesapeake Beach.
- Decide how long to go for: Now that you're up to speed on Chesapeake Beach, you can work out the ideal length of your holiday. Put together a draft itinerary and allocate enough time to cover everything you want to do.
- Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to pick a Chesapeake Beach holiday package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
