Holiday rentals with outdoor seating in North Beach

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5-star retreat for those who value tranquility over spectacle. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our 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.

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.

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*

Patuxent River View

🌊 Nestled near North Beach, Herrington Harbor, Herrington on the Bay, and Chesapeake Beach, this serene guest house offers a peaceful escape for travelers of all kinds—whether you’re exploring local sights, reconnecting with nature, visiting family, or just passing through. Guests enjoy thoughtful amenities at no extra cost: a fully stocked kitchen, complimentary coffee and tea, high-speed WiFi, a pool and gazebo, and more comforts to make you feel right at home.

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!

Beach Home | King Bds | Firepit | Backyard Dining

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.

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is located on the Patuxent River, outside of Solomons Island with a view of the river's opening to the Chesapeake Bay. The 16-acre property is adjacent to our very private conservation area that borders our 300-foot private beach. The year-round property has a pier, and in-ground pool (May-October) with amazing river views. Also hosts weddings+events up to 100 guests (additional event fee applies).

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Savor our three-bedroom Cottage in this peaceful western shore spot, enjoy two acres of green space, the pier, kayaks, swings, fire pit, shady lawns & sun-drenched loungers, local waterfront dining or eat in, close to Washington, D.C., Annapolis, & Baltimore at this honeymoon-worthy country-like micro-resort. Due to the current COVID-19 situation, we have offered SPECIAL discounts for longer-term rentals