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Chesapeake 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
Chesapeake Bay Waterfront Home w/ Hot Tub
A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l winter dates**
$500 per night
SUPERHOST
Home in North Beach
Light of North Beach
This is a 1 bed/1 bath apartment with private keyless entry located off the backyard of my home, keeping it very private. I live upstairs so there may be minimal upstairs sounds from my family. There is no shared spaces. I live in a residential neighborhood but the area is incredibly quiet. It is approximately half a mile walk to get to the boardwalk/pier, coffee shops and restaurants from my home. There is a driveway in front of my home for 1 vehicle and there is free on street parking.
$100 per night
SUPERHOST
Cottage in Chesapeake Beach
Coastal Pet-Friendly Cottage <½ Mi to Beaches
Escape to Chesapeake Beach and relax effortlessly thanks to this 2-bed, 1-bath cottage! Sporting a spacious fenced-in backyard with cushioned patio furniture, this vacation rental is the epitome of seaside living. Spend your days soaking up the sun at Brownie’s Beach or casting off with Reel Attitude Charters! Out-of-towners will love the ability to visit Washington D.C. for the day, and those looking to unwind from every day will simply love beach days filled with sun, family, and friends.
$111 per night

Stay near Chesapeake Beach's top sights

Photo of Rod 'N' Reel Restaurant
Rod 'N' Reel Restaurant51 locals recommend
Photo of Traders Seafood Steak & Ale
Traders Seafood Steak & Ale17 locals recommend
Photo of Abners Crab House
Abners Crab House23 locals recommend
Photo of Bayfront Park
Bayfront Park9 locals recommend
Photo of Neptune's Seafood Pub
Neptune's Seafood Pub29 locals recommend
Photo of Mamma Lucia By the Bay
Mamma Lucia By the Bay6 locals recommend

Chesapeake Beach house rentals

Private room in Port Republic
Bayview at Hilltop
$71 per night
Home in North Beach
Warm Home Overlooking the Chesapeake Bay
$250 per night
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Home in Chesapeake Beach
Bahia Breeze - Bayfront Cottage
$315 per night
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Home in North Beach
Spacious Beach House Top Floors - Walk Everywhere!
$188 per night
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Home in North Beach
Waterfront North Beach Home ~ 2 Mi to Beach!
$255 per night
Home in North Beach
Chesapeake Bay, Maryland, Beach Front Paradise
$564 per night
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Home in North Beach
Sweet Bamboo
$185 per night
Home in North Beach
Waterfront Beach House, 45 minutes to DC!
$339 per night
SUPERHOST
Home in Chesapeake Beach
Staycation at Cozy Beach Home
$215 per night
Home in North Beach
Charming Herrington Bay Cottage
$215 per night
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Home in North Beach
Picnic Cottage
$189 per night
Home in Chesapeake Beach
Come Stay on the Bay! Beautifully Renovated Oasis
$318 per night
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Chesapeake Beach cabin rentals

Cabin in Lusby
Peaceful Waterfront Retreat on The Bay
$154 per night
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Cabin in Lusby
Hideaway on the Bay: Waterfront Vintage A Frame
$274 per night
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Cabin in North Beach
1943 Beach House Walk to Town & Beach & Boardwalk.
$136 per night
Cabin in Lusby
2-bedroom lake-house with a magnificent view
$242 per night
SUPERHOST
Cabin in Lusby
Lakeside Cabin with Arcade & Firepit
$280 per night
SUPERHOST
Cabin in Lusby
Your own private beach?? Horizon views of the bay?
$400 per night
SUPERHOST
Cabin in Reedville
Dinna Fash-3 BR Waterfront Log Cabin
$173 per night
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Cabin in Colonial Beach
Peaceful Water Front Cabin on Winery Grounds
$135 per night
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Cabin in Goldsboro
Wigwam Lodge & Hot Tub~MasterSuite~Woodland Views
$188 per night
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Cabin in Nanticoke
La Cabaña
$175 per night
Cabin in Lusby
Cozy Cabin in Scenic Southern MD
$172 per night
Cabin in Reedville
Coastal Cabin - hot tub, private beach & kayaks
$299 per night
SUPERHOST

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