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$217 per night from 28 Sept to 29 Sept
S$217
28 Sept - 29 Sept
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
Relaxing
"Excellent stay"

Reviewed on 15 Sept, 2025

Rod 'N' Reel Resort
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
The price is S$132 per night from 1 Oct to 2 Oct
S$132
1 Oct - 2 Oct
includes taxes & fees
8/10 Very Good! (1,004 reviews)
"When it takes two tries to get the room key to"

Reviewed on 16 Sept, 2025

St Michaels Inn
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$144 per night from 28 Sept to 29 Sept
S$144
28 Sept - 29 Sept
includes taxes & fees
8.8/10 Excellent! (888 reviews)
"The room was very nice"

Reviewed on 17 Sept, 2025

Sonesta ES Suites Annapolis
See all 752 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$53
per adult
Chesapeake Beach: Guided Walking Tour of the Railway Trail
Chesapeake Beach Guided Walking Tour - Railway Trail

Chesapeake Beach Guided Walking Tour - Railway Trail

S$53
per adult
Chesapeake Beach Guided Walking Tour - Railway Trail
North Beach: North Beach Scenic Guided Walking Tour

North Beach: North Beach Scenic Guided Walking Tour

S$53
per adult
North Beach: North Beach Scenic 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.