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Chesapeake Beach beach vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Chesapeake Beach

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Home in North Beach
Warm Home Overlooking the Chesapeake Bay
Sitting on the Chesapeake Bay, North Beach is a town where you are so close to things, yet can feel so far away. Only 45 minutes form Washington, DC, you can sit on one of three decks and gaze into the Chesapeake Bay, enjoying all that small town life has to offer. An open plan, with defined spaces, the house is at once cozy (with a fireplace) and spacious for a family. It is great for couples, adventurers, business travelers, and families. This is not a house for large groups or parties.
$190 per night
Townhouse in North Beach
Tropical w/Beach Passes, Deck, Desks -Dog Friendly
Welcome to A Haven Away! Relax in a plant-filled oasis 10 mins from the beach, boardwalk, and a cute beach town. Walk to ice cream & coffee shops, or wetlands. Lots of fresh seafood! We'll share a town guide, including tips for day trips. Perfect for remote working (2 desks) or families (pack n play, child-size mattress). Fully equipped kitchen; 3 character-filled bedrooms; a TV with Netflix, Max, and Prime, and an outdoor deck to lounge under string lights! Find us on IG @ahavenaway.
$105 per night
Cottage in North Beach
Club Carp North Beach - Steps to the Bay!
Welcome to Club Carp North Beach. A charming and cozy cottage just 3 blocks to the Boardwalk/Beach. Renovated throughout with three bedrooms and two full baths. Perfect place for a relaxing, family vacation! This kid-friendly home has a large fenced yard with a swing set, play area for the kiddos, and lots of extra amenities with families in mind. Comfortable outdoor dining area with fire pit and gas grill. Just steps to restaurants, shopping, and bars. (We are at Dayton and 7th st).
$151 per night

Stay near Chesapeake Beach's top sights

Rod 'N' Reel Restaurant51 locals recommend
Traders Seafood Steak & Ale17 locals recommend
Bayfront Park9 locals recommend
Abners Crab House23 locals recommend
Neptune's Seafood Pub29 locals recommend
Roland's of Chesapeake Station20 locals recommend

Chesapeake Beach vacation rentals

Tiny home in Solomons
“Cabana by the Bay”-tiny home on a pier!
$148 per night
Guesthouse in Stevensville
Waterfront Getaway - View of bay from your bed
$164 per night
Apartment in Lexington Park
Adorable Waterfront Apartment Weekend Getaway
$90 per night
Apartment in Port Republic
Bayview Apartment with a private entrance.
$99 per night
Cottage in Deale
Rockhold Creek Cottage
$210 per night
Cabin in Lusby
Peaceful Waterfront Retreat on The Bay
$119 per night
Guesthouse in Galesville
Gorgeous water view studio!
$165 per night
Cottage in North Beach
Full house rental in Twin Beach. 1 bk from the Bay
$198 per night
Guest suite in Chesapeake Beach
Nice Guest Suite at Chesapeake Bay
$128 per night
Home in Chesapeake Beach
Tide’s end beautiful home two blocks from the bay.
$77 per night
Bungalow in North Beach
Bayside Bungalow: Cozy North Beach Getaway
$185 per night
Cottage in North Beach
Quiet Coastal Cottage Escape with Water Views
$130 per night

Destinations to explore