Chesapeake Beach Holidays

Photo by Ronanne Vinson

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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

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Fully refundableReserve now, pay when you stay
The price is S$155 per night from 17 Nov to 18 Nov
S$155
17 Nov - 18 Nov
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
we did not have the breakfast, the beds are amazingly comfortable rooms spotless. The water pressure was poor. The staff was over the top helpful and friendly. We would definitely stay again.

Reviewed on 25 Oct, 2025

Rod 'N' Reel Resort
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$123 per night from 30 Nov to 1 Dec
S$123
30 Nov - 1 Dec
includes taxes & fees
8.8/10 Excellent! (934 reviews)
Staff and property are awesome!

Reviewed on 31 Oct, 2025

Sonesta ES Suites Annapolis
Spark by Hilton Waldorf

Spark by Hilton Waldorf

3 out of 5
11770 Business Park Drive, Waldorf, MD
Fully refundableReserve now, pay when you stay
The price is S$115 per night from 28 Nov to 29 Nov
S$115
28 Nov - 29 Nov
includes taxes & fees
8.6/10 Excellent! (27 reviews)
Everything was great

Reviewed on 2 Nov, 2025

Spark by Hilton Waldorf
See all 736 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.

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: Guided Walking Tour of the Railway Trail

Chesapeake Beach: Guided Walking Tour of the Railway Trail

S$61
per adult
Chesapeake Beach: Guided Walking Tour of the Railway Trail
Chesapeake Beach: Private Sailing Cruise on a 42-Foot Yacht

Chesapeake Beach: Private Sailing Cruise on a 42-Foot Yacht

S$900
per traveller
Chesapeake Beach: Private Sailing Cruise on a 42-Foot Yacht
North Beach: North Beach Historic Guided Walking Tour

North Beach: North Beach Historic Guided Walking Tour

S$61
per adult
North Beach: North Beach Historic Guided Walking Tour
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.