Cottage vacation rentals in Calvert County

4.98 out of 5 average rating, 280 reviews

Cottage in Lusby

Gettin to the point. ( Cove Point Beach)

Our beach house is for you to enjoy Cove Point Beach, which is only 500 ft away. The kitchen is fully stocked, or use the outdoor grill on the side of the house.PLEASE NON SMOKERS ONLY. One dog allowed on a cases by case bases with a one time pet fee of $65.00. No children under 8 years old. Walk to the beach, but only park your vehicle in our driveway, not on beach inlets. A gas fireplace in the living room. A beautiful sun porch area to enjoy. Enjoy walking on this private community beach.

4.96 out of 5 average rating, 172 reviews

Bell Estates I Beautiful Cottage I *Beach Passes*

Bell Estates is a newly built corner lot across the street from the bay with minimal views of the water from Master bedroom and front yard. Located in the heart of North Beach in the exclusive Holland Point neighborhood, our home provides a cozy get-a-way for a family looking to escape the hustle and bustle of life. Home is 2 minutes away from Herrington Harbor, Ketch 22, North Beach Boardwalk & more. Enjoy local accessibility to fishing from the boardwalk dock or rent a boat to go crabbing.

4.95 out of 5 average rating, 172 reviews

Club Carp North Beach - Steps to the Bay!

Calendar open for bookings in April 2025! Welcome to Club Carp North Beach. A charming and cozy cottage just 3 blocks to the Boardwalk/Beach. Renovated throughout with 3 bedrooms and 2 full baths. Perfect place for a relaxing, family vacation! This kid-friendly home has a large fenced side yard with swing set, play area for the kiddos, and lots of extra amenities with families in mind. Comfortable outdoor dining area with fire pit and gas grill. Just steps to restaurants, shopping, and bars.

5 out of 5 average rating, 45 reviews

Cottage in Hollywood

The Little Blue Cottage

Escape to this peaceful waterfront cottage and enjoy everything the crick life has to offer. You can start your day drinking coffee on the porch rockers watching the birds do their morning routine and finish your day drinking a cold beverage enjoying the sunset colors on the water. Bring your Kayaks and SUP boards or fishing rods or crab lines to catch them off the new pier. Bike to the local Greenwell State Park or Sotterly Plantation. Enjoy farmlands and horse farms all around you.

Cottage in Chesapeake Beach

4.93 out of 5 average rating, 61 reviews

Cliffside Bay Cottage: Pet-Friendly, Easy DC Drive

Chesapeake Beach cottage on a secluded waterfront property with stunning bay views. Only 45 mins from DC and a 5 minute drive to the beach or dining & shops in Chesapeake Beach and North Beach. Main room features a double bed, loveseat, streaming TV, desk/workspace, small fridge & microwave. Full bath. Patio deck with firepit and another TV. This space is really for the couple or a single person looking for a relaxing bay getaway (and bring along a pet or 2). No kids b/c of the cliff.

5 out of 5 average rating, 24 reviews

Cottage in Lusby

Cozy Cottage close to Beaches & Solomon’s Island

Explore Southern Maryland in a cozy, renovated Victorian cottage on a quiet, private cul-de-sac surrounded by trees. You’ll be close to a lot of fun places! 5 minutes to Vera’s Restaurant & marina 6 minutes to Calvert Cliffs State Park & Beach (3.1 miles) great for shark teeth sifting 7 minutes to Flag Ponds Nature Pk & Beach 2.8 miles 12 minutes to Annmarie Sculpture Garden 7 miles 12 minutes to Calvert Marine Museum 8.2 mi 16 minutes to Solomon’s Island 9.5 miles

4.93 out of 5 average rating, 15 reviews

Cottage in Lusby

Riverside Haven w/ Hot Tub

Unplug and unwind at Riverside Haven, a cozy waterfront cabin for two overlooking the Chesapeake Bay. Dog-friendly and designed for comfort, it’s perfect for couples or solo travelers. Enjoy complimentary coffee, free Wi-Fi, a private hot tub, a fire pit and access to a small public beach next to the property. Wake up to stunning sunrises and relax in peaceful, natural surroundings—Riverside Haven is your perfect coastal escape.

4.97 out of 5 average rating, 248 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.

4.99 out of 5 average rating, 82 reviews

Cottage in Hollywood

Cottage on the Creek

The Cottage is perfectly perched alongside Cuckold Creek showcasing the beauty of Southern Maryland. Our home provides plenty of space for relaxing together with a water view everywhere you turn. Each space is set up to provide you with the comforts of home, so you can relax and enjoy being in the moment. Located in the heart of Hollywood, not too far from stores or restaurants, but still "away from it all". ✨

4.93 out of 5 average rating, 68 reviews

Cozy Waterfront Cottage - Pet Friendly

Original waterfront cottage in North Beach is perfect for a small family or two couples. Beautiful sunrises and moonrises over the boardwalk from the front deck. Walk to restaurants and nightlife, stroll the boardwalk, chill on the beach or go to the spa or charter fishing in Chesapeake Beach. Pet friendly. Beach Passes, umbrella and chairs included. 2 bedrooms plus a twin daybed that pulls out to queen bed.

4.87 out of 5 average rating, 186 reviews

Full house rental in Twin Beach. 1 bk from the Bay

A block from the Chesapeake Bay and North Beach boardwalk, this charming beach cottage is the perfect place for a weekend away by the water but still close to the activities of the DMV. Great location for groups who have booked fishing excursions on the bay or families in town for a wedding celebration. During the week, enjoy easy access to commuter busses to DC, with pickup only steps away.