Waterfront vacation rentals in Chesapeak Ranch Estates

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Top-rated waterfront rentals in Chesapeak Ranch Estates

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

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Top guest favorite

The exterior of a two-story white house is depicted, featuring large windows and a brown roof. Green landscaping surrounds the house, with a wooden pathway leading to the dock. The scene is illuminated by warm evening light, enhancing the peaceful waterfront setting.

Apartment in California

4.93 out of 5 average rating, 230 reviews

Our Little Piece of Heaven

Our cozy studio apartment sets on the Patuxent River. With the perfect views of Myrtle Beach, Point Patient and Thomas Johnson Bridge. Relax watching the boats and birds or take a walk along the water for a lovely neighborhood to stroll for 2.5 miles. Your favorite moments may be when you wake to see the sun rise and again to see the orange sky set. Just over the bridge from the popular Solomon's Island which is full of fabulous restaurants, boat rentals, charter fishing and summer concerts.

Superhost

Cabin in Lusby

4.92 out of 5 average rating, 218 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Guest favorite

A set of four white woven chairs with striped cushions surrounds a small round table, positioned on a stone patio overlooking a sandy beach. The calm waters of Chesapeake Bay gently lap at the shore, with a clear sky in the background.

Home in Lusby

4.98 out of 5 average rating, 100 reviews

Waterfront with sweeping bay view & private beach

Year-round private beach oasis on Chesapeake Bay! Perfect Fall & Winter Escape. An hour from DC beltway & world away. Recharge & relax to the sound of waves & sailboats. Spacious & fully renovated, with modern features, ample outdoor terraces. Enjoy long walks, nature spotting (bald eagles, rays, dolphins), shark tooth collecting. Kayaks provided! Short drive to Solomons Island, and local amenities: restaurants, bars, store, national parks & vineyards. No parties or events. Only relaxing.

Top guest favorite

A stone fire pit area with four wooden chairs is situated near the water. A wooden dock leads to the lake, surrounded by lush greenery and trees, creating a serene outdoor space for relaxation.

Cabin in Lusby

4.98 out of 5 average rating, 101 reviews

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

Welcome to The Lake House - our freshly updated 3 bedroom, 3 bath cabin on Lake Vista with views of the Patuxent River/Chesapeake Bay from the private pier. Enjoy everything Southern Maryland has to offer all within a 10 minute drive - Calvert Cliffs, Flag Ponds, Solomons Island - hiking, fishing, boating and beaches. Located just 90 minutes outside DC, The Lake House will become your new go-to retreat from the hustle. Come relax and make memories on the water with your family and friends.

Top guest favorite

Home in Lusby

5 out of 5 average rating, 154 reviews

Historic Rousby Hall, Waterfront, Pool, Beach

**Heated pool open to Nov 2. Thanksgiving chef dinner options** Rousby Hall is a stunning 5-star waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee additional).

Top guest favorite

A serene outdoor area is depicted, featuring a well-maintained lawn and stone pathway leading towards the water. The view overlooks a marina with boats docked, surrounded by trees and residential properties. Comfortable lounge chairs are positioned on a deck, inviting relaxation.

Home in Solomons

5 out of 5 average rating, 104 reviews

The Little House on Back Creek

Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

Top guest favorite

Two light blue Adirondack chairs are positioned on a wooden dock, facing a calm river. The sun sets over the water, casting a warm glow across the surface and creating a serene atmosphere. A weathered wooden table is placed nearby, enhancing the inviting scene.

Guest suite in Lusby

4.98 out of 5 average rating, 357 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is Solomon’s island. This is a safe space for all🥰

Top guest favorite

The inviting exterior of the cottage is framed by lush greenery and trees, with a gravel driveway leading up to the entrance. Large windows illuminate the front façade, highlighting the simple yet charming design of the one-story building against a clear blue sky.

Home in Leonardtown

5 out of 5 average rating, 135 reviews

White Point Cottage -- Quiet Waterfront Getaway

Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. More on IG @whitepointcottage, and be sure to visit our sister property, Water's Edge Cottage.

Top guest favorite

A collection of various fossilized shark teeth is displayed on an orange background. The teeth are of different sizes and shapes, showcasing both small and large specimens, with some exhibiting intricate details. The vibrant color of the background contrasts with the dark tones of the teeth.

Home in Lusby

4.95 out of 5 average rating, 114 reviews

Soul Oasis - home on the Chesapeake Bay

You can hear the waves of the Chesapeake Bay from the new trex deck. The beach is a short walk away where you can find fossils and sharks teeth and see plenty of nature. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.

Top guest favorite

Guesthouse in Bushwood

4.93 out of 5 average rating, 164 reviews

Little House by the water

Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. However, the space is small and it is really a studio apartment as I think the pictures make evident.

Top guest favorite

Apartment in Lexington Park

5 out of 5 average rating, 395 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!

Guest favorite

The image features the historic Cove Point Lighthouse, a tall white structure beside a spacious two-story keeper's house with a red roof. A small building is visible nearby. The well-maintained lawn and pathways lead towards the water's edge under a clear blue sky.

Lighthouse in Lusby

4.89 out of 5 average rating, 106 reviews

Cove Point Lighthouse Keeper's House- Side A

UPDATE: CPLH Reservations are paused until August 12th. Please check back for future dates! Listed on the National Register of Historic Places and cared for by the Calvert Marine Museum (CMM), the Cove Point Lighthouse historic site has been lovingly restored and re-purposed so that it can be enjoyed by all. The active lighthouse and keeper's home sit on a seven-acre point of land in one of the narrowest points of the Chesapeake Bay.