Beachfront vacation rentals in Calvert Beach-Long Beach

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Top-rated beachfront rentals in Calvert Beach-Long Beach

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Top guest favorite

A spacious living area features large windows offering unobstructed views of the water. A comfortable sectional sofa is complemented by decorative cushions. A coffee table is positioned in front, with planters adding greenery. A wall-mounted television is visible, alongside a cozy fireplace.

Home in North Beach

5 out of 5 average rating, 134 reviews

Waterfront, Dog-friendly, Hot Tub, Peleton, Bikes

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 living room features white wicker furniture adorned with blue cushions, arranged on a striped area rug. Large windows allow natural light to fill the space, highlighting a gas fireplace and nautical-themed decor on the walls.

Cottage in Lusby

4.98 out of 5 average rating, 272 reviews

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.

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

4.97 out of 5 average rating, 127 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 serene waterfront view showcases the Chesapeake Bay, stretching towards the horizon under a clear sky. The shoreline features wooden docks and gentle waves, while quaint homes are seen along the sandy beach. Green trees provide shade in the foreground.

Home in Saint Leonard

4.9 out of 5 average rating, 130 reviews

Perfect Bay and Beach Getaway one hour from DC!

Our waterfront home with sweeping views of the Chesapeake Bay is close to beaches, the Flag Harbor Marina, Solomon's Island, Flag Pond Nature Preserve and Calvert Cliffs State Park. You’ll love the spectacular sunrises/sunsets over the Bay, diving ospreys and eagles, and exploring the bay by kayak, canoe, or paddle board. Our house is great for families (with kids), groups, and well-mannered dogs. New in 2023: we will be replaced the upstairs HVAC system, baby proofing, and fall 2023 paint

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, 182 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.

Guest favorite

A tranquil view from the porch features a colorful hammock, inviting relaxation amidst lush green grass. The landscape stretches to the water in the distance, framed by trees and an open sky, creating a serene atmosphere.

Home in Montross

4.99 out of 5 average rating, 150 reviews

Beach Please! River cottage w/private beach & dock

Come unwind at "Beach, Please!" Our renovated cottage on the river with a private beach and dock is waiting for you! What's there to do? There's boating, fishing, crabbing, bird watching, tanning, and hammock-napping. Need more? Ok, antique shops, breweries, wineries, live music, crab boils and oyster fests. Still need more? Cornhole, can jam, horseshoes, hiking, and swimming and tennis at the community pool. That's not all, so just trust us - you will LOVE your time in Montross, Virginia!

Top guest favorite

Large glass doors open to reveal a spacious deck overlooking the Chesapeake Bay. The deck features a dining table and chairs, with potted plants adding a touch of color, while the calm water glistens in the sunlight.

Home in Lusby

4.95 out of 5 average rating, 170 reviews

Waterfront Home on the Chesapeake Bay-Pvt Beach

A commanding view of the Chesapeake Bay. Enjoy walking the beach to Calvert Cliffs, bike to parks, art and cultural events. Enjoy the private beach with plenty of fine sand and gentle waves, great for teaching little one's water skills, playing with your canine companion or fishing/crabbing off the beach. You’ll love this waterfront hideaway because of the location, views, and the ambiance. My place is suburb for couples, solo adventurers, business travelers, families, and canine friends.

Top guest favorite

A cozy living area is shown with a light brown leather sofa positioned near a glass door leading to outdoor views. A black television is mounted on the wall, and a small table with a tray sits in the foreground. Natural light filters through sheer curtains.

Place to stay in Annapolis

4.94 out of 5 average rating, 119 reviews

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

*Hot tub* “Chesapeake Bay View Paradise" (3BR/2BA Penthouse Suite). Private penthouse level of a 2-level duplex, new deck, gorgeous Chesapeake Bay views, steps to sandy beach. 3 car parking. Gourmet kitchen, SS appl, granite counters, bar. Comfy living & dining areas. Entry handrail installed 9/20/24. 2 King BR, 1 Queen BR + Queen sleeper sofa in living area. Sleeps 8. 2 spa inspired baths, 1 jetted 2-person Jacuzzi tub inside. Outdoor Spa with Jets * Best Places To Stay Annapolis

Top guest favorite

Home in Tracys Landing

4.99 out of 5 average rating, 206 reviews

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower, an outdoor redwood panoramic barrel sauna and a redwood cold plunge!

Top guest favorite

A wooden pier extends over calm water, leading to a two-story home with large windows and a welcoming deck. Brightly colored chairs sit in the yard, alongside a grassy area and trees. Two kayaks are visible on the pier, ready for use.

Home in Lexington Park

4.96 out of 5 average rating, 162 reviews

Private beach retreat in historic St. Mary's City

Nestled next to historic St Mary's City and a lovely state park, your Lucas Cove Beach home awaits you with your own private sandy beach and pier with vast views of the water, new salt water hot tub steps away from the beach, four beautifully furnished bedrooms with Casper mattresses, an upstairs deck with adirondack chairs to take in the water views and amazing sunrises while sipping a beverage or just relaxing, high speed Wi-Fi. Kayaks avail for rent.

Guest favorite

Home in Cambridge

4.98 out of 5 average rating, 126 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

Top guest favorite

A charming single-story house is framed by vibrant pink flowering trees. The facade features yellow siding, blue shutters, and a turquoise front door. A white picket fence encloses the front yard, which is well-maintained with green grass and landscaping.

Home in North Beach

4.97 out of 5 average rating, 142 reviews

Getaway at the Beach w/ King Beds & Yard

Welcome to Palm Haven at A Haven Away! Our home has 4 bedrooms (2 king beds + 2 queen beds). 2 mins to the beach, restaurants, and wetlands. We have a private, landscaped backyard perfect for dining and lounging. We provide beach passes, beach gear, games, a Pack & Play, and tips for jet ski rentals and day trips. The shed has a huge Smart TV. Fully-equipped kitchen. Single-story living with 2 bedrooms, accessible shower on the ground floor.