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Beachfront vacation rentals in Dares Beach

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Top-rated beachfront rentals in Dares Beach

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

Guest favourite
Home in Shady Side
Luxe Modern Chesapeake Waterfront Oasis
The Cottage at Silverwater is a lesson in quiet luxury, compelling architecture, unimaginable views and endless comforts. Original fine art and luxe bedding envelope you in a modern, light-filled space. Outside you will be treated to an expansive waterfront lawn that is great for games and afternoon sun. Rest on modern lounges or watch the sunset on your private waterfront bluestone patio tucked into the sea grass. As a guest favorite, your fabulous getaway is here—just read the reviews!
Guest favourite
Guest suite in Leonardtown
Happy Guesthouse! Located waterfront
Quaint 1000 sq foot 1 bedroom apartment with awesome water view and waterfront accessibility. Walk to downtown and wharf in Leonardtown, MD. close to restaurants and historic sites. Use of dock and garden. Dock your boat at the premises! Small Pet friendly with additional cleaning fee Beautifully decorated and private. Kitchen not equipped with stove, but has hot plate, microwave and toaster oven. Self check-in. Pet and children friendly, owners on site but very private.
Guest favourite
Apartment in Lexington Park
Adorable Waterfront Apartment Weekend Getaway
Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Popular amenities for Dares Beach beachfront rentals

Pet-friendly beachfront home rentals

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Guest suite in Colonial Beach
Bayview Bungalow
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Guesthouse in Glen Burnie
The Crab House - a Private, Waterfront Guest House
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Home in Cambridge
Jewell on the Chesapeake
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Home in Grasonville
River Front, Private Single Family Home
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Apartment in Lexington Park
Historic St. Mary's City, MD
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Home in Lusby
Coastal Oasis On The Chesapeake, King Bd sleeps 12
Superhost
Home in Montross
Potomac Waterfront Home and Estate
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Home in Lusby
Waterfront Home on the Chesapeake Bay-Pvt Beach
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Guest suite in Stevensville
Kent Island Haven - A Waterfront Getaway
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Cottage in Colonial Beach
River view dog friendly YOLO Beach House
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Guest suite in Piney Point
Spectacular beachfront walk-out in Piney Point MD
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Home in Newburg
The River House, a Wicomico Beach Retreat

Beachfront home rentals with a pool

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Home in Montross
Beach Please! River cottage w/private beach & dock
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Home in Hague
Year-Round River Escape with Indoor Pool & Beach
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Guesthouse in Queenstown
Waterfront Getaway
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Condo in Colonial Beach
Rooftop bay and river views
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Home in Dameron
Dameron Farm on the Water - Saltwater Pool
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Guesthouse in Colonial Beach
Beach Carriage House with Pool and Cabana
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Camper/RV in Stevensville
Charming RV With A Water View
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Apartment in Port Republic
Scientists Cliffs Fossil Beach Apt Hike over Cliff
Home in Montross
Idyllic Montross Vacation Rental Home w/ Views
Home in Saint Michaels
Bankors Aweigh | an ESVR property
Guest favourite
Home in Stevensville
Lavish Waterfront Home In Sought After Kent Island
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Home in Tilghman Island
Breathtaking Views & Tranquility

Private beachfront home rentals

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Cottage in Leonardtown
Beach Front and 'Perfectly Placed'
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Cottage in Colonial Beach
Cozy cottage 3 blocks from beach
Superhost
Cottage in Wittman
"Wittman Cottage"
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Home in Annapolis
Cozy 2br home w/ parking in downtown Annapolis
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Apartment in Crownsville
“River Sweet" Private Apartment
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Home in St. Leonard
Cozy Cottage on the Chesapeake Bay
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Apartment in Pasadena
Sea Dreamer aka Phenomenal Hospitality
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Home in Annapolis
Cape St Claire waterfront getaway
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Home in Lexington Park
Private beach retreat in historic St. Mary's City
Superhost
Home in Colonial Beach
*WATERFRONT BEACH HOUSE PARADISE*
Guest favourite
Home in Colonial Beach
Beach Blonde Cottage
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Home in Cambridge
Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Destinations to explore