Beachfront holiday rentals in Chesapeake Beach

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Top-rated beachfront rentals in Chesapeake Beach

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

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Guest favourite

Home in Shady Side

5.0 out of 5 average rating, 116 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

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!

12–19 Feb

$604 SGD per night

Guest favourite

Flat in North Beach

4.97 out of 5 average rating, 102 reviews

Bayside Oasis of Southern Maryland

1 1/2 blocks from the beautiful Chesapeake Bay. Walk to boardwalk, restaurants and shopping. Beach opens, with some restrictions, May 28, 2021. Free beach pass provided. Quiet friendly town where everyone knows your name. King bed, private bath with shower (no tub). Free WiFi, private off street parking, 45” TCL-Roku TV, Echo Dot, Keurig w/pods for coffee and tea, full kitchen (no dishwasher), beach chairs, beach towels, dishes, flatware, pots pans. Chesapeake Beach is 1-mile south on Rt 262.

19–26 Aug

$208 SGD per night

Superhost

Home in North Beach

4.84 out of 5 average rating, 178 reviews

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.

20–27 Oct

$373 SGD per night

Guest favourite

Cottage in Saint Leonard

4.99 out of 5 average rating, 102 reviews

Captain Jack's Bay Hideaway

This beach cottage sits just across the street from the Chesapeake Bay on the Western Shore. You'll have access to two private community beaches where you can sit, relax, and just enjoy the scenery. If you are an early riser, you can enjoy beautiful sun rises over the bay. If you search the sand, you might even find fossils, including shark teeth! Close proximity to Washington DC, Annapolis, and Baltimore. There are a lot of local restaurants and shopping. You will not be disappointed.

18–25 Jul

$237 SGD per night

Guest favourite

Cottage in Leonardtown

4.97 out of 5 average rating, 125 reviews

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

21–28 Sep

$248 SGD per night

Guest favourite

Flat in Crownsville

4.98 out of 5 average rating, 164 reviews

“River Sweet" Private Apartment

River Sweet has everything you need for a fun and relaxing getaway. Cozy and clean, River Sweet provides all the comforts of home, including your own driveway and entrance. You'll delight in privacy while enjoying a safe, waterfront neighborhood. A local mini mart and restaurant are close by. And, you are centrally located between Annapolis, Baltimore and Washington for fun excursions! Please let us know if you need a long-term stay. We would be happy to accommodate you.

28 Jun – 5 Jul

$169 SGD per night

Guest favourite

Guest suite in Dunnsville

5.0 out of 5 average rating, 239 reviews

The Bird's Nest at Holly Bluff-Riverfront. Beach.

This is a studio apartment above detached garage, with a balcony and seating. The property sits on the Rappahannock River- guests are welcome to use the beach and dock! Property has a private entrance and bathroom, which is located on the first floor. Apartment is up a flight of stairs above the garage. Plenty of parking. We have self check in and ample space for social distancing. We welcome all tenants! The Birds Nest is a perfect getaway destination for relaxing and fun.

20–27 Aug

$158 SGD per night

Guest favourite

Guest suite in Tilghman Island

4.96 out of 5 average rating, 114 reviews

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

21–28 Nov

$201 SGD per night

Guest favourite

Flat in Lexington Park

5.0 out of 5 average rating, 316 reviews

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!

14–21 Nov

$120 SGD per night

Guest favourite

Home in Tracys Landing

4.99 out of 5 average rating, 166 reviews

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower.

11–18 Dec

$626 SGD per night

Guest favourite

Tiny home in Solomons

4.95 out of 5 average rating, 538 reviews

“Cabana by the Bay”-tiny home on a pier!

This tiny home is a newly renovated cabana sitting on a pier. Fall asleep to the sound of waves crashing under you! Enjoy shared use of our private beach. Kayaks and bikes are available April-October and are stored directly across the street. Go crabbing or fishing off the pier and walk to one of the many nearby restaurants. Check out the summer concert series at the Calvert Marine Museum.

18–25 Jan

$194 SGD per night

Guest favourite

Cottage in North Beach

4.96 out of 5 average rating, 273 reviews

Waterfront Cottage Near Herrington and North Beach

Escape to Osprey Cottage, a renovated oasis overlooking the Chesapeake Bay. Our home is a 1930s bungalow that has been tastefully updated with modern sensibility, while still preserving its original charm. Streamlined decor, gleaming wood floors, and stunning views from the common spaces, deck, and hot tub invite you to simply relax.

26 Jul – 2 Aug

$339 SGD per night