Chesapeake Beach Holidays

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Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Chesapeake Beach Beach Holiday

Get prepared to live out those beachy daydreams on your Chesapeake Beach holiday. Go on a romantic walk, admire the beautiful ocean vistas and pick up unique shells and rocks during your trip to Chesapeake Beach. Just 10 kilometres from downtown, Breezy Point Beach is the place to be for many sun-seeking visitors. Browse our Chesapeake Beach holiday deals and watch your travel budget stretch further!

Top hotels in Chesapeake Beach

Rod 'N' Reel Resort
Rod 'N' Reel Resort
3 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Fully refundableReserve now, pay when you stay
The price is S$201 per night from 9 Dec to 10 Dec
S$201
includes taxes & fees
9 Dec - 10 Dec
8.2/10 Very Good! (1,002 reviews)
"As I said nice area with casino next door"

Reviewed on 19 Nov,2024

Rod 'N' Reel Resort
La Quinta Inn by Wyndham Waldorf
La Quinta Inn by Wyndham Waldorf
2.5 out of 5
11770 Business Park Dr, Waldorf, MD
Fully refundableReserve now, pay when you stay
The price is S$123 per night from 2 Dec to 3 Dec
S$123
includes taxes & fees
2 Dec - 3 Dec
7.4/10 Good! (970 reviews)
"Very confortable place"

Reviewed on 21 Nov,2024

La Quinta Inn by Wyndham Waldorf
Sonesta ES Suites Annapolis
Sonesta ES Suites Annapolis
3 out of 5
170 Admiral Cochrane Dr, Edgewater, MD
Fully refundableReserve now, pay when you stay
The price is S$155 per night from 1 Dec to 2 Dec
S$155
includes taxes & fees
1 Dec - 2 Dec
8.6/10 Excellent! (708 reviews)
"It was a nice, well equipped sweet that met our needs. The two bedroom option was perfect for us."

Reviewed on 29 Oct,2024

Sonesta ES Suites Annapolis
See all 691 properties in Chesapeake Beach
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

How much does a Chesapeake Beach holiday package cost?
From just . Yes, you read that correctly. Our Chesapeake Beach holiday packages are a simple way to make your dollar go further. Bundle your flights, hotels and rental car and discover this top destination.
How do I get a cheap travel package to Chesapeake Beach?
One of the easiest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, hotels, activities and rental cars — we’ve got everything you need. Select the combination that best suits you and watch your savings stack up. Of course, a package deal is never one-size-fits-all. That’s why Expedia offers over 550 air carriers and 1,000,000 hotels around the globe, which lets you customize your Chesapeake Beach getaway.
Where should I stay in Chesapeake Beach?
We recommend staying near the action. Many people favor hotels around popular sights, like Chesapeake Beach Water Park, Breezy Point Beach and Chesapeake Beach Railway Museum.
What are the top hotels in Chesapeake Beach?
Get your holiday off to a fantastic start by locking in a room at Amazing Waterfront Destination For Romantic And Family Holidays. It’s one of most popular hotels in Chesapeake Beach. Another cosy option is Coastal Pet - Friendly Cottage <½ Mi To Beaches.
How far in advance should I book my Chesapeake Beach holiday?
While not all airlines advertise tickets early, you can usually look up international fares on Expedia up to a year in advance. This is the time when you’ll score some fantastic deals. If you’ve left things to the last minute, there’s a chance you could get lucky. Low prices occasionally appear only weeks before departure.
What does an Expedia Chesapeake Beach travel package include?
Car rentals, hotels and flights — we bring you the best deals. All you have to do is figure out your preferred combination. After you’ve made your booking, you can add on the exciting stuff like activities and sightseeing tours. Our travel packages make it easy to put together an amazing Chesapeake Beach holiday.
What should I know before booking a Chesapeake Beach travel package?
An Expedia travel package can be tailored to your budget and is a fantastic way to make your money go further. How much you include is your call. Rental cars, hotels and flights — choose any combination that suits your style.
Can I choose my airline with a Chesapeake Beach Expedia holiday package?
You can, and with over 550 airlines to choose from across the globe, you’ve got lots of choice. Browse the available options and find out which airline best suits your budget and needs.
If I'm not able to travel, can I cancel my Chesapeake Beach holiday package?
Plans can change unexpectedly, so yes, you can. You may be able to cancel or alter your Chesapeake Beach holiday package for free if you’ve booked in the last 24 hours. For bookings older than that, you can still cancel and rebook, but your car rental company, airline or hotel may charge a fee. Need more information? Look up our Customer Service Portal. We’re here to help make sure your trip goes off without a hitch.

Popular places to visit

Rod n Reel Charter Fishing

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.

Rod n Reel Charter Fishing

What to do in Chesapeake Beach

Chesapeake Beach: North Beach Historic Guided Walking Tour

Chesapeake Beach: North Beach Historic Guided Walking Tour

S$58
Per adult
Chesapeake Beach: North Beach Historic Guided Walking Tour
Chesapeake Beach: North Beach Scenic Guided Walking Tour

Chesapeake Beach: North Beach Scenic Guided Walking Tour

S$58
Per adult
Chesapeake Beach: North Beach Scenic Guided Walking Tour
Chesapeake Beach: Guided Walking Tour of the Railway Trail

Chesapeake Beach: Guided Walking Tour of the Railway Trail

S$58
Per adult
Chesapeake Beach: Guided Walking Tour of the Railway Trail
See all activities in Chesapeake Beach

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.