Vacation rentals in Chesapeake Beach

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Top-rated vacation rentals in Chesapeake Beach

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Guest favorite

The vintage A-frame home is nestled amongst trees, featuring a deck with a canopy in the foreground. A stone path leads to the entrance, where large windows allow for ample natural light. The surrounding landscape is adorned with greenery and decorative plants.

Cabin in Lusby

4.93 out of 5 average rating, 213 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 comfortable living area features a plush blue sofa with pink accent pillows, complemented by a round mirror. Decorative plants add a touch of greenery. A light wooden coffee table supports a floral arrangement, while two poufs create additional seating in a welcoming space.

Townhouse in North Beach

4.97 out of 5 average rating, 212 reviews

Walk to Beach! King Bed & Free Beach Passes

Welcome to Bay Haven at A Haven Away! Relax in a fully-equipped, plant-filled oasis with a king bed primary suite that our guests love. Its prime location is in walking distance to the beach, restaurants, fresh seafood, and wetlands. We’ll share our beach passes and lots of local recommendations so you can enjoy our little slice of heaven. 12 min walk to the beach, boardwalk, restaurants, and kids play areas in cute North Beach, MD 7 min drive to Herrington Harbor 14 min drive to Tacaro Estate

Top guest favorite

A comfortable living area is framed by large windows showcasing a vibrant sunset over the water. Soft furnishings include two chairs with decorative pillows and a coffee table. Plants are positioned thoughtfully, enhancing the serene atmosphere.

Home in North Beach

5 out of 5 average rating, 153 reviews

Waterfront, Dog-friendly, Hot Tub, Peleton

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l winter dates**

Top guest favorite

The exterior of the houseboat is shown with a modern design and a spacious rooftop deck adorned with vibrant umbrellas. A wooden walkway leads to the structure, which is positioned on calm waters, accompanied by a small boat moored nearby.

Houseboat in Grasonville

4.99 out of 5 average rating, 190 reviews

Cass-Away A Luxury Houseboat

Kent Narrows Rentals welcomes you aboard Cass-Away! A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a living room, kitchen, 2 bedrooms, 2 full baths, and a magnificent view from the rooftop deck! With 9 waterfront bars/restaurants within walking distance, you can get a taste of what the eastern shore has to offer. Minutes from the Bay Bridge and a short drive to Annapolis, D.C., St. Michael’s, and Ocean City. NO Fishing/Crabbing on property! Check our website for more info!

Guest favorite

The image displays a one-room apartment featuring a king bed, kitchen area, and dining table. Soft lighting enhances the modern décor, with decorative rugs and artwork adorning the walls. A window allows natural light to brighten the space, creating a functional and inviting atmosphere.

Apartment in North Beach

4.96 out of 5 average rating, 140 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.

Guest favorite

A charming cottage sits at the water's edge, surrounded by lush greenery. A wooden staircase leads down from an elevated deck to the sandy beach. Two blue chairs are positioned on the deck, inviting relaxation as the sun sets in the background.

Cottage in Leonardtown

4.96 out of 5 average rating, 218 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.

Top guest favorite

A bright sun porch features a round glass dining table surrounded by four light-colored chairs. Large windows provide views of the waterfront, allowing natural light to fill the space. A cozy seating area is visible in the background, offering a serene atmosphere.

Home in Leonardtown

5 out of 5 average rating, 133 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.

Guest favorite

The a-frame cabin is framed by lush green trees, set in a serene natural environment. Large windows are visible on the cabin's façade, enhancing the connection with the surrounding landscape. Sunlight filters through the foliage, casting gentle light on the cabin's exterior.

Cabin in Colonial Beach

4.95 out of 5 average rating, 162 reviews

Summer Perfect, Water Front A-frame on Winery

This serene cabin is on the Ingleside Vineyard's property. Have a glass or two of wine and walk around the vineyards and then retreat to your own private a-frame cabin oasis. A beautiful view of the Roxsbury Estate where abundant wildlife can be viewed all around the property and the pond is stocked and ready to be fished. Within driving distance to wineries, Stratford Hall, George Washington & James Monroe's birthplace, Westmoreland State Park, and the beach town of Colonial Beach.

Top guest favorite

A red umbrella provides shade over a square table with a glass top, accompanied by two cushioned chairs. Lush green grass surrounds the seating area, framed by tall trees and distant views of the water, creating a serene outdoor space.

Apartment in Port Republic

4.96 out of 5 average rating, 222 reviews

Serenity Suite on Chesapeake Bay

Come enjoy our waterfront home on the scenic Calvert Cliffs. Relax by the water under mature shade trees. Take in beautiful Bay views in Adirondack chairs with stunning vistas. Photograph wildlife. Comfortable ½ mile walk to private community bay shoreline. Have breakfast in the yard while enjoying the sunrise. Stroll the community shoreline and explore fossil hunting, hike at nearby trails and enjoy dinner on Solomon’s Island. Then open the windows to listen to waves overnight.

Guest favorite

The bungalow features a welcoming front porch enclosed by large windows, allowing natural light to fill the space. The exterior showcases white siding complemented by green trim and a simple pathway lined with landscaping stones, leading to the entrance surrounded by a grassy yard.

Bungalow in North Beach

4.87 out of 5 average rating, 109 reviews

Bayside Bungalow: Cozy North Beach Getaway

Sip your morning coffee while overlooking the Bay, hear the waves splashing up on the beach, and smell breakfast being made by the local bakery. Our little bungalow is located at the end of the Boardwalk, making for an easy stroll to the shops, a variety of eateries and ice cream shops, try a little shopping, or just relax on the beach all afternoon. Be on the water AND close to all that the beach has to offer for entertainment. *Beach Passes STAY with the home upon checkout*

Top guest favorite

The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.

Guesthouse in Stevensville

4.99 out of 5 average rating, 300 reviews

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Guest favorite

A serene waterfront scene showcases a calm bay under a sky filled with vibrant oranges and blues. A shaded seating area with a table and chairs, complemented by a grill, is positioned beside the rocky shoreline, framed by wooden posts.

Guest suite in Chesapeake Beach

4.96 out of 5 average rating, 118 reviews

Nice Guest Suite at Chesapeake Bay

Take it easy at this unique and tranquil getaway. Come and relax in our modern & comfortable guest suite to enjoy a small-town quiet setting with amazing Chesapeake Bay views. A short drive from Washington DC (45 min), Annapolis (30 Min), or Baltimore (1 hr). Groceries, boardwalks, restaurants are all within walking distance. Enjoy cable TV, high-speed Internet, and strong wifi through Xfinity.