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Chesapeake Beach vacation rentals

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Top-rated vacation rentals in Chesapeake Beach

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

Cottage in North Beach
Quiet Coastal Cottage Escape with Water Views
Want to get away? Come relax and escape in our updated bay view cottage. You'll enjoy stunning sunsets, warm surroundings, and all the amenities you could want in our cozy, peaceful cottage home. You'll find plenty of comfortable spots to relax, inside and out. Located on a quiet street, while still close to the small-town charm and offerings of North Beach, Chesapeake Beach, and Herrington Harbor. Walk along the bay, enjoy the local restaurants, and get ready to relax. Stay a week and save!
$162 per night
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Cottage in Chesapeake Beach
NEW! Adorable Beach Cottage w/ Hot Tub & Tiki Bar!
With calm bayside waters, plenty of fishing opportunities, and a variety of family-friendly attractions, Chesapeake Beach truly offers something for everyone, and there's no better launch point to explore it all than this 2-bedroom, 1-bath cottage. Aside from the property's convenient location (just a half mile to beaches), you'll love the thoughtfully curated outdoor amenities, including a private hot tub, a fire pit, a tiki bar, and more. The perfect couple's getaway or family vacation awaits!
$197 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).
$193 per night
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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 Neptune's Seafood Pub
Neptune's Seafood Pub29 locals recommend
Photo of Bayfront Park
Bayfront Park9 locals recommend
Photo of Mamma Lucia By the Bay
Mamma Lucia By the Bay6 locals recommend

Chesapeake Beach house rentals

Home in North Beach
Light of North Beach
$83 per night
Home in North Beach
Chesapeake Bay Waterfront Home w/ Hot Tub
$489 per night
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Private room in Port Republic
Bayview at Hilltop
$71 per night
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Home in Chesapeake Beach
Tide’s end beautiful home two blocks from the bay.
$77 per night
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Home in Edgewater
Chesapeake Bay Waterfront Getaway Cozy Beach Views
$180 per night
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Home in North Beach
Chesapeake Bay, Maryland, Beach Front Paradise
$493 per night
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Home in North Beach
Seascape
$122 per night
Home in Deale
Waterfront Couple GetAway w/Hot tub & Kayaks
$305 per night
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Home in North Beach
Warm Home Overlooking the Chesapeake Bay
$168 per night
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Home in Huntingtown
Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck
$334 per night
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Home in North Beach
NEW! North Beach 'Blue Heron Bungalow' w/ Backyard
$264 per night
Home in Chesapeake Beach
Bahia Breeze - Bayfront Cottage
$197 per night
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Chesapeake Beach cabin rentals

Cabin in Lusby
Peaceful Waterfront Retreat on The Bay
$149 per night
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Cabin in North Beach
1943 Beach House Walk to Town & Beach & Boardwalk.
$134 per night
Cabin in Lusby
Hideaway on the Bay: Waterfront Vintage A Frame
$221 per night
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Cabin in Lusby
2-bedroom lake-house with a magnificent view
$252 per night
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Cabin in Gambrills
Relaxing Cabin Get Away Near Annapolis & DC
$85 per night
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Cabin in Lusby
Cozy Cabin in Scenic Southern MD
$148 per night
Cabin in Lusby
Lakeside Cabin with Arcade!
$289 per night
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Cabin in Lusby
Your own private beach?? Horizon views of the bay?
$350 per night
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Cabin in Mechanicsville
Cozy Country Cabin
$181 per night
Cabin in Saint Michaels
TRUE ST MICHAELS 6 ACRE WATERFRONT!!
$638 per night
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Private room in Port Republic
Scientists Cliffs Beach Queen Bedroom 1 hr from DC
$428 per night
Cabin in Cambridge
Cabin on the Creek
$500 per night
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