Vacation rentals in Calvert County

4.9 out of 5 average rating, 102 reviews

Cottage in North Beach

Quiet Coastal Cottage Escape with Water Views

Want to get away? Come relax and escape in our updated bay view cottage. You'll enjoy stunning sunsets, warm surroundings, and all the amenities you could want in our cozy, peaceful cottage home. You'll find plenty of comfortable spots to relax, inside and out. Located on a quiet street, while still close to the small-town charm and offerings of North Beach, Chesapeake Beach, and Herrington Harbor. Walk along the bay, enjoy the local restaurants, and get ready to relax. Stay a week and save!

4.93 out of 5 average rating, 203 reviews

An outdoor fire pit is surrounded by several black adirondack chairs, creating a cozy gathering space. The scene is set against a backdrop of lush trees and St. Leonard's Creek, with dusk settling in and a soft blue hue filling the sky.

Cabin in Lusby

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 --

4.96 out of 5 average rating, 198 reviews

Townhouse in North Beach

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

A sandy beach extends along the shore, meeting the calm waters under a pastel sky. A lighthouse stands tall in the distance, accompanied by a house with a red roof. The shoreline appears tranquil, with gentle waves lapping at the sand.

4.99 out of 5 average rating, 212 reviews

Cove Point Cottage with Chesapeake Bay views

Welcome to our beach house, just a block from the Cove Point Beach on the Chesapeake Bay. Start your beach day by grabbing the beach wagon from the shed, loading it up with beach chairs, towels, and your cooler. A short stroll takes you to the beach, where you can spend the day searching for shark teeth and shells or swimming in the bay's refreshing waters. After a day in the sun, rinse off in our outdoor shower. Our shady patio provides the perfect spot to relax and enjoy the evening breeze.

4.98 out of 5 average rating, 347 reviews

Guest suite in Lusby

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🥰

A lighthouse rises against a colorful sunset, with vibrant clouds reflected in the water. The sandy beach curves alongside the rocky shoreline, while the quaint white structure with red accents stands prominently, showcasing a serene coastal scene.

5 out of 5 average rating, 185 reviews

Cove Point Beach Home 1 &1/2 blocks to Beach

"Welcome to our Beach House, located in the unique peaceful private beach community of Cove Point. You'll enjoy the tranquility and the beauty of living less than a 2 min walk to the sandy beach and just a few away from Solomon's Island, MD. Our home was just renovated and is ready for your family to enjoy, offering beach necessities (wagon, chairs, umbrella, & toys) and recreational equipment (bikes & kayaks). This will be your home away from home.

4.9 out of 5 average rating, 266 reviews

A wooden dock features railings and lighting, leading down to calm waters reflecting the twilight sky. Silhouetted trees frame the serene scene, emphasizing the tranquility of the natural surroundings. The path is well-defined, providing clear access to the waterfront.

Cabin in Lusby

Peaceful Waterfront Retreat on The Bay

Escape to a serene waterside cabin with a private dock on quiet St. Leonard Creek, just an hour from Washington, DC. This rustic studio offers a cozy retreat for solo travelers, couples, or small families looking for peace and relaxation. Whether you're here to unwind, work remotely, or explore the outdoors, you'll find plenty to enjoy—including two kayaks, two canoes, and stunning waterfront views.

4.96 out of 5 average rating, 643 reviews

Two wicker chairs with cushioned seating are positioned on a wooden deck, offering a view of the water. A decorative marlin sculpture is mounted on the wall, adding a coastal touch. The gentle movement of the water is visible in the background.

Tiny home in Solomons

“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. 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.

4.96 out of 5 average rating, 187 reviews

A tranquil waterfront setting features a multi-level home surrounded by trees, with a spacious deck visible. Adirondack chairs on the dock face the calm waters, reflecting the structure and greenery. Soft outdoor lighting adds a cozy ambiance, enhancing the serene landscape.

Guesthouse in Lusby

Cozy Lakeside Studio Retreat.

Cozy basement studio that provides a perfect get away. From beach combing, kayaking, fishing, swimming in the Bay, dock, fire pit, and corn hole, there’s lots to do. Or simply just relax and enjoy the serene surroundings. Photography package available, message host for details 2 GUESTS ONLY; please check with host regarding children

4.97 out of 5 average rating, 329 reviews

A wooden pier extends into calm waters, with posts lining the edges. The sky displays soft hues of pink and blue, while wispy clouds are scattered above. The tranquil scene invites relaxation and contemplation near the Chesapeake Bay.

Cottage in North Beach

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.

4.99 out of 5 average rating, 302 reviews

Cove Point Beach Cabin

My place is close to shopping, restaurants and dining in Lusby and Solomons Island, the Chesapeake Bay, and family-friendly activities. You’ll love my place because of the comfy beds, the coziness, and the views. My place is good for couples, solo adventurers, business travelers, and families (with kids). No pets allowed.

4.96 out of 5 average rating, 142 reviews

A hot tub is situated outdoors, surrounded by a gravel area. Water is seen bubbling inside, indicating a relaxing atmosphere. The hot tub is designed with a round shape and features built-in seating. Natural light creates soft reflections on the water's surface.

Cottage in Saint Leonard

Block to Private Beach, Screened deck, Hot Tub

Relax at this renovated cottage with views of the Chesapeake Bay! Features large screened deck, hot tub, around corner from private community beach where you can find fossils and shark teeth! (4 min drive to larger community beach.) (No cleaning fee and multi night discounts! Message us for monthly rates.)

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Calvert County vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Calvert County

Superhost

A decor piece shaped like a crab is mounted on a neutral wall. The crab is created from wooden planks painted in varying shades of blue and white, adding a coastal touch to the space.

Home in North Beach

4.92 out of 5 average rating, 36 reviews

Light of North Beach

EmilyRating, 5 stars1 week ago

A great stay at a relaxing quiet beach town! Walking distance to the boardwalk and local trails, while still feeling private and safe.

Superhost

Cabin in Lusby

4.88 out of 5 average rating, 8 reviews

COZY BLACK LoG HoUSe

WendyRating, 5 stars3 weeks ago

The house has been beautifully remodeled. Beds were comfortable and overall the home was well laid out. Location is in a neighborhood and about a five - seven minute drive to Calvert Cliffs Park and shopping. Driveway has ample room for two cars. Everything we used in the house worked well. Plenty of games to keep the kids (and adults) entertained. There is a beautiful deck out back but no chairs set up. ☹️ Adding chairs there and a grill would be excellent additions to the home. We had a great stay and the host was very responsive. Grandkids had a successful shark tooth hunt and left happy!

5 out of 5 average rating, 15 reviews

Cottage in Lusby

Cozy Cottage close to Beaches & Solomon’s Island

LindaRating, 5 stars4 weeks ago

Emilio and Wanda’s home was absolutely lovely. They thought of everything to make our stay so enjoyable. Would recommend to anyone wanting a relaxing stay. So very close to Solomon’s Island. Thank you Emilio and Wanda!

4.95 out of 5 average rating, 162 reviews

Loft in Solomons

Stunning Waterfront Chef's Loft

MalyaRating, 5 stars3 weeks ago

Most incredible location, super cozy and beautifully decorated Airbnb! You’re surrounded by water views from every window and have access to an adorable balcony plus a little sand area below. The hosts were very accommodating. The area is the heart of Solomon’s island and walking distance to great spots. Highly recommend this Airbnb!

5 out of 5 average rating, 5 reviews

Large glass doors lead to a wooden deck, revealing a serene outdoor seating area with multiple chairs. Sunlight filters through trees in the background, and a cozy indoor seating area is visible, featuring a coffee table with books and a decorative bowl.

Home in Saint Leonard

Waterfront Home, Spectacular View & Private Beach!

MargaretRating, 5 stars3 weeks ago

We had a great stay here. Beautiful views of the water. Hosts were quick to respond. Good WiFi. Large deck with teak table and weber grill. Easy walk to water access. The waterfront is the best I’ve seen on the Bay. Sandy with shady and sunny spots against the cliffs. From the water access, you can walk in one direction to the limestone cliffs for shark tooth hunting. The other direction goes all the way to the marina. We hope to stay here again.

4.96 out of 5 average rating, 55 reviews

Home in Chesapeake Beach

Bahia Breeze - Beachfront Cottage

KellyRating, 5 stars3 weeks ago

This was a cute little home to stay at over the weekend. Only downside was having to pay for beach access. But the house itself was very nice and had all the kitchen items we needed. Would stay again.

4.94 out of 5 average rating, 50 reviews

The exterior of a charming yellow cottage is featured, surrounded by a white picket fence. A welcoming front porch is accessible via a set of steps, with multiple windows allowing natural light to enter. Lush greenery and colorful flowers enhance the inviting facade.

Cottage in North Beach

Cozy Waterfront Cottage - Pet Friendly

LisaRating, 5 stars3 days ago

This was a fantastic vacation rental- the kids’ favorite yet! You can’t beat the views and the proximity to the beach and shops. There is also a playground, library, ice cream shop, and pizza just a block away. The host had snacks, water, and milk available for us and the kids when we arrived, which was very welcome after a long car ride! And having beach chairs and beach umbrellas for use made our beach days so much better! We brought our paddle board and launched it off the local beach which was quite fun. Annapolis and DC are both far drive and, when we weren’t enjoying the local amenities, we found plenty to do just an hour drive or less away. I highly recommend this rental. Thank you for allowing us to rent your lovely home and we will definitely be back

A panoramic view of the Chesapeake Bay is captured from a deck railing, showcasing calm waters and a clear sky. The surrounding greenery adds a natural touch, creating a serene backdrop for relaxation and contemplation.