Holiday houses in Calvert Cliffs

4.93 out of 5 average rating, 203 reviews

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 --

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 348 reviews

Historic St.Mary's City at the Lazy Bear Cottage

Inquire first on pets, there is a 50 lb. weight limit total, can be split up between 2 small dogs or 1 at 50lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

5 out of 5 average rating, 371 reviews

Loft in Lusby

Treetop Loft Retreat w/ Private Beach Access

Come experience our tucked-away loft 5 minutes from beaches, 10 minutes to Solomons, and Calvert Cliffs. Private above-garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, & kitchen (convection oven, induction burner, microwave, refrigerator, and Keurig). Enjoy quick Wi-Fi, a 40" Smart TV, a cozy queen bed, and comfy lounge chairs. Bring S'mores fixings to roast over the fire and wrap yourself in a blanket. Choose to stay in or adventure out.

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.

4.95 out of 5 average rating, 161 reviews

Loft in Solomons

Stunning Waterfront Chef's Loft

Looking for a truly unique getaway? You've found it in the Chef's Loft. Located at the top of our recreational cooking school, it offers stunning panoramic water views from every window! While you're here, take part in one of our cooking classes. All guests receive a 10% discount. The loft is close to area museums, a sculpture garden, fishing, hiking trails, fossil hunting, wine tasting and more! Discover why Coastal Living Magazine named Solomons one of the "happiest places in America!"

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🥰

4.96 out of 5 average rating, 190 reviews

Cottage in Leonardtown

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.

Apartment in Lexington Park

5 out of 5 average rating, 383 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!

5 out of 5 average rating, 184 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.

4.97 out of 5 average rating, 235 reviews

Cottage in California

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has an open floor plan that allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum featuring live concerts by top name bands.

4.9 out of 5 average rating, 266 reviews

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

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.

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Other great holiday rentals in Calvert Cliffs

Superhost

Cabin in Lusby

4.88 out of 5 average rating, 8 reviews

COZY BLACK LoG HoUSe

WendyRating, 5 stars2 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!

4.89 out of 5 average rating, 64 reviews

Beachfront Oasis with Amazing Views

NguyetRating, 5 stars3 weeks ago

We had such a wonderful stay! The kitchen was incredibly well stocked—honestly better than my own at home—with 5-6 large pots, an Instant Pot, every spice you could think of,peelers (which saved me!), and both a NutriBullet and a regular blender. It made cooking for the family a breeze. The kid had a blast on the trampoline, and we all loved the easy beach access with calm waters perfect for swimming all day and kayaking. The beach was also perfect for a peaceful morning run, and at night we could see the lighthouse light on the water. The porch quickly became our favorite spot—we gathered there to watch a rainstorm and were treated to a stunning double rainbow. The sky was full of stars at night, creating such a peaceful atmosphere. The grill on the porch made cooking super convenient. We enjoyed being close to a large park where we played pickleball. The beds were large and comfortable—everyone slept really well. Michael was a fantastic host—very attentive and accommodating.

4.99 out of 5 average rating, 80 reviews

Home in Hollywood

Waterfront Home: Osprey Getaway

DamarisRating, 5 starstoday

⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️ We came here to celebrate my daughter graduating from HS. This place is perfectly prepared and exactly as described. In a nutshell, the home is brand new and beautifully designed, yet tastefully simple, all in an amazing-looking and peaceful setting. Garrett and Lauren thought about everything. I am so used to renting AirBNBs and always having to pack extra "stuff" in case the towels end up being too thin, or the bed sheets below standards. THAT WAS NOT THE CASE here. The hosts made sure to have high-quality and clean linens, towels, appliances, furniture, mattresses, you name it... They did not cut corners, which reflects the utmost respect to guests. Wonderful experience. Thank you, Garrett and Lauren, for the awesome home, kindness, and above and beyond attention before, during, and after our stay.

Home in Saint Leonard

4.87 out of 5 average rating, 52 reviews

Hickory House on the Chesapeake Bay!

DamonRating, 5 stars2 weeks ago

Great neighborhood. Close to the water.

Apartment in Port Republic

4.97 out of 5 average rating, 205 reviews

Serenity Suite on Chesapeake Bay

KristaRating, 5 stars2 days ago

This is our second time staying at this cozy and tranquil retreat—and it won’t be our last. We first came here six months ago for a quiet getaway from the kids, and we liked it so much we knew we’d be back. This time was just as wonderful. The place is spotless, peaceful, and incredibly relaxing. The view of the bay is absolutely stunning—calm, quiet, and the perfect backdrop for unwinding. The hosts are warm and welcoming, and the space has everything you need for a comfortable and refreshing stay. If you’re looking for a serene escape with beautiful scenery and thoughtful touches, this is the place. We’re already planning our next visit.

4.72 out of 5 average rating, 211 reviews

Apartment in Lusby

Nice view self-contained Apart.

MargaretRating, 5 stars1 month ago

I really enjoy staying here at nice view. very peaceful and close to work. has everything I need and very comfortable bed. always responsive when I had a question. would definitely stay here again.

Superhost

4.88 out of 5 average rating, 41 reviews

Waterfront home with three bedrooms,3 full baths

BreckRating, 5 stars5 days ago

Dale is an incredibly proactive and helpful host. He checked in with us several times to ensure we had everything we need and went out of his way to meet us on our schedule to check in and show us around. This is a great spot to relax and look at the ocean or an easy commute to Solomon's Island and all its amenities. You also get access to the community's private beach, which is beautiful and a real asset!