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Beachfront vacation rentals in Chesapeake Beach

Find and book unique beachfront homes on Airbnb

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Top-rated beachfront rentals in Chesapeake Beach

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

Guest favorite
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!
$328 per night
Guest favorite
Home in Grasonville
River Front, Private Single Family Home
Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away
$178 per night
Guest favorite
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!
$90 per night

Popular amenities for Chesapeake Beach beachfront rentals

Pet-friendly beachfront home rentals

Guest favorite
Guest suite in Colonial Beach
Bayview Bungalow
$97 per night
Guest favorite
Guesthouse in Glen Burnie
The Crab House - a Private, Waterfront Guest House
$184 per night
Guest favorite
Cottage in Westover
Rumbley Cottage on the Tangier Sound-Private Beach
$279 per night
Superhost
Cottage in Reedville
Private point on the Bay🌤hammock, hot tub, kayaks❤️
$185 per night
Guest favorite
Guest suite in Leonardtown
Happy Guesthouse! Located waterfront
$100 per night
Guest favorite
Guest suite in Stevensville
Kent Island Haven - A Waterfront Getaway
$200 per night
Guest favorite
Home in Lusby
Coastal Oasis On The Chesapeake, King Bd sleeps 12
$399 per night
Guest favorite
Home in Cambridge
Jewell on the Chesapeake
$200 per night
Guest favorite
Apartment in Lexington Park
Historic St. Mary's City, MD
$144 per night
Guest favorite
Cottage in Colonial Beach
River view dog friendly YOLO Beach House
$130 per night
Guest favorite
Cottage in Westover
Heaven on the Bay - A Peaceful Waterfront Retreat
$165 per night
Guest favorite
Home in Lusby
Waterfront Home on the Chesapeake Bay-Pvt Beach
$380 per night

Beachfront home rentals with a pool

Guest favorite
Home in Montross
Beach Please! River cottage w/private beach & dock
$250 per night
Guest favorite
Home in Hague
Year-Round River Escape with Indoor Pool & Beach
$485 per night
Guest favorite
Guesthouse in Queenstown
Waterfront Getaway
$172 per night
Guest favorite
Condo in Colonial Beach
Rooftop bay and river views
$155 per night
Superhost
Cottage in Heathsville
Riverfront Retreat with PRIVATE POOL and BEACH!!
$329 per night
Guest favorite
Home in Heathsville
Ask about discount - cottage with pool and dock!
$332 per night
Guest favorite
Camper/RV in Stevensville
Charming RV With A Water View
$195 per night
Guest favorite
Home in Dameron
Dameron Farm on the Water - Saltwater Pool
$444 per night
Guest favorite
Guesthouse in Colonial Beach
Beach Carriage House with Pool and Cabana
$249 per night
Superhost
Condo in Crisfield
3 Bedroom Waterfront Condo with Pool and Boat slip
$200 per night
Guest favorite
Home in Stevensville
Lavish Waterfront Home In Sought After Kent Island
$557 per night
Home in Saint Michaels
Bankors Aweigh | an ESVR property
$383 per night

Private beachfront home rentals

Guest favorite
Cottage in Colonial Beach
Cozy cottage 3 blocks from beach
$115 per night
Superhost
Cottage in Wittman
"Wittman Cottage"
$156 per night
Guest favorite
Cottage in Leonardtown
Beach Front and 'Perfectly Placed'
$170 per night
Guest favorite
Apartment in Crownsville
“River Sweet" Private Apartment
$88 per night
Guest favorite
Home in Annapolis
Cozy 2br home w/ parking in downtown Annapolis
$123 per night
Guest favorite
Apartment in Pasadena
Sea Dreamer aka Phenomenal Hospitality
$87 per night
Guest favorite
Home in Annapolis
Cape St Claire waterfront getaway
$140 per night
Guest favorite
Home in Lexington Park
Private beach retreat in historic St. Mary's City
$353 per night
Guest favorite
Home in Colonial Beach
Beach Blonde Cottage
$142 per night
Guest favorite
Cabin in Reedville
Dinna Fash-3 BR Waterfront Log Cabin
$124 per night
Guest favorite
Home in Heathsville
Waterfront Potomac & Chesapeake Bay 2 Kayaks Dock
$249 per night
Guest favorite
Home in St. Leonard
Cozy Cottage on the Chesapeake Bay
$225 per night

Destinations to explore