
North Beach, Chesapeake Beach
10/14 – 10/20
$289/nighttotal: $1734 (6 )
Tilghman Island Retreat By Knapps Narrows!
1 1cottage , Tilghman Island
This Tilghman Island cottage offers convenient access to Phillips Wharf Environmental Center, Knapp's Narrows Marina & Inn, and Kronsberg Park, all within a 10-minute walk, with Back Creek Community Park and Tilghman Island Marina a short 15-minute walk away.
The two-bathroom vacation home includes a fully equipped kitchen with microwave and dishwasher, a relaxing patio, free Wi-Fi in public areas, and free self-parking, perfect for a relaxing Tilghman Island getaway.
The two-bathroom vacation home includes a fully equipped kitchen with microwave and dishwasher, a relaxing patio, free Wi-Fi in public areas, and free self-parking, perfect for a relaxing Tilghman Island getaway.

North Beach, Chesapeake Beach
10/13 – 10/15
$440/nighttotal: $880 (2 )
Cozy Waterfront Cottage - Pet Friendly
1 1apartment , North Beach
This North Beach waterfront cottage offers stunning sunrise and moonrise views over the Chesapeake Beach boardwalk, with easy walking access to restaurants and nightlife.
The two-bedroom, one-bathroom house sleeps five, features a fully equipped kitchen including a dishwasher, offers air conditioning, a private garden, parking, and includes beach passes, an umbrella, and chairs; nearby attractions include the Chesapeake Beach spa and charter fishing.
The two-bedroom, one-bathroom house sleeps five, features a fully equipped kitchen including a dishwasher, offers air conditioning, a private garden, parking, and includes beach passes, an umbrella, and chairs; nearby attractions include the Chesapeake Beach spa and charter fishing.

North Beach, Chesapeake Beach
09/08 – 09/15
$676/nighttotal: $4732 (7 )
Waterfront Lifestyle At Historic Bay Dreams
4 2apartment , North Beach
This historic waterfront inn, the "Waterfront Inn of Holland Point," is located on the western shore of the Chesapeake Bay, one mile from Herrington Harbour and less than a mile from Rose Haven Memorial Park beach.
This four-bedroom, two-bathroom rental accommodates up to ten guests with a waterfront porch, direct yard access to a firepit and picnic area, and is equipped with WiFi, a dishwasher, and air conditioning, allowing pets for a fee.
This four-bedroom, two-bathroom rental accommodates up to ten guests with a waterfront porch, direct yard access to a firepit and picnic area, and is equipped with WiFi, a dishwasher, and air conditioning, allowing pets for a fee.

North Beach, Chesapeake Beach
09/08 – 09/15
$264/nighttotal: $1848 (7 )
Sea La Vie
1 2apartment , North Beach
Sea la Vie, a three-bedroom North Beach house, is centrally located for easy access to local attractions.
This pet-friendly vacation rental boasts a full kitchen with dishwasher, two bathrooms, sleeps eight, and includes a private garden and parking.
This pet-friendly vacation rental boasts a full kitchen with dishwasher, two bathrooms, sleeps eight, and includes a private garden and parking.

North Beach, Chesapeake Beach
10/13 – 10/15
$880/nighttotal: $1760 (2 )
Beachfront Paradise | Walk To Restaurants & Shops
1 1apartment , North Beach
This North Beach rental sits directly on the boardwalk, offering easy access to the beach and nearby restaurants, shops, and the farmer's market. The apartment has received excellent ratings for location, cleanliness, and user experience.
The home features three bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a private patio with a fire pit, laundry facilities, and a parking pass for a designated green space.
The home features three bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a private patio with a fire pit, laundry facilities, and a parking pass for a designated green space.

North Beach, Chesapeake Beach
09/08 – 09/15
$330/nighttotal: $2310 (7 )
Bayfront Boardwalk Condo W/ Sunrise Views
1 2apartment , North Beach
This North Beach apartment is located directly on the boardwalk, just steps from the beach and a short walk from restaurants, shops, and attractions in both North Beach and Chesapeake Beach. It consistently receives excellent ratings for its cleanliness, location, and overall experience.
This two-bedroom, one-bathroom rental comfortably accommodates six guests with a king-sized bed in the master, a queen-sized bed in the guest room, and a queen-sized sofa bed in the living room. The apartment is equipped with a well-stocked kitchen, a private patio with stunning sunrise views, free beach passes, a dedicated parking space, and access to a garden and an elevator.
This two-bedroom, one-bathroom rental comfortably accommodates six guests with a king-sized bed in the master, a queen-sized bed in the guest room, and a queen-sized sofa bed in the living room. The apartment is equipped with a well-stocked kitchen, a private patio with stunning sunrise views, free beach passes, a dedicated parking space, and access to a garden and an elevator.

North Beach, Chesapeake Beach
09/08 – 09/15
$209/nighttotal: $1463 (7 )
Sweet Bamboo Beach Cottage
3 2apartment , North Beach
This North Beach apartment is just a short walk from the beach, boardwalk, and restaurants, offering easy access to the area's attractions and a charming, relaxed atmosphere. The apartment boasts excellent ratings for location, cleanliness, and overall user experience, making it a great choice for travelers seeking a comfortable and convenient stay.
The spacious 3-bedroom apartment comfortably accommodates 6 guests with a total floor area of 960 square feet. Enjoy a fully equipped kitchen, a relaxing outdoor living space, and access to a spa, garden, and parking, ensuring a comfortable and enjoyable stay.
The spacious 3-bedroom apartment comfortably accommodates 6 guests with a total floor area of 960 square feet. Enjoy a fully equipped kitchen, a relaxing outdoor living space, and access to a spa, garden, and parking, ensuring a comfortable and enjoyable stay.

North Beach, Chesapeake Beach
10/14 – 10/20
$735/nighttotal: $4410 (6 )
Water-view Deale Home: Walk To Marina, Restaurants
1 1cottage , Deale
This Deale cottage rental is conveniently located within 9 miles of Franklin Point State Park, the Upper Youghiogheny River, Shadyside Park, Galesville Heritage Museum, and the Captain Avery Museum.
The 3.5-bathroom house features a fireplace, fully equipped kitchen with microwave and dishwasher, private patio, and free self-parking plus WiFi; it's perfect for exploring Deale's attractions.
The 3.5-bathroom house features a fireplace, fully equipped kitchen with microwave and dishwasher, private patio, and free self-parking plus WiFi; it's perfect for exploring Deale's attractions.

North Beach, Chesapeake Beach
09/08 – 09/15
$557/nighttotal: $3899 (7 )
Chesapeake Bay Breezes - Cozy Coastal Family Stay
4 2apartment , North Beach
This brand-new apartment rental in North Beach is situated just four blocks from the waterfront and boardwalk, offering a highly walkable 10-minute stroll to the beach, shops, restaurants, and breweries.
This 2,700+ sq ft home accommodates up to 8 guests with four bedrooms and five bathrooms, featuring two primary suites, a bonus room, a rear deck, and a private two-car driveway, perfect for families or groups seeking comfort and convenience.
This 2,700+ sq ft home accommodates up to 8 guests with four bedrooms and five bathrooms, featuring two primary suites, a bonus room, a rear deck, and a private two-car driveway, perfect for families or groups seeking comfort and convenience.

North Beach, Chesapeake Beach
10/13 – 10/15
$392/nighttotal: $784 (2 )
Spacious House, Great Deck & Grill, Close To Boardwalk, Shops, And Restaurants.
3 1apartment , North Beach
This three-bedroom house in North Beach is close to the Chesapeake Bay, the boardwalk, and the beach. It's also within easy reach of Annapolis, Washington DC, Northern Virginia, and Baltimore. The house has an excellent user rating.
The house has 1,700 square feet of floor space and can accommodate up to nine guests. It has three bedrooms, three bathrooms, a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a Jacuzzi, a garden, and parking. The house also has a porch with rockers, a deck with a table, umbrella, seating for six, and a propane grill, and a large flat backyard for kids to play.
The house has 1,700 square feet of floor space and can accommodate up to nine guests. It has three bedrooms, three bathrooms, a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a Jacuzzi, a garden, and parking. The house also has a porch with rockers, a deck with a table, umbrella, seating for six, and a propane grill, and a large flat backyard for kids to play.

North Beach, Chesapeake Beach
10/13 – 10/15
$1186/nighttotal: $2372 (2 )
North Beach Bayview Retreat With Bay Views
4 1apartment , North Beach
This 3600 sq ft, 4-story condo is located in North Beach, a 4-minute walk to the North Beach Pier and adjacent to shops and dining, offering exceptional bay views.
This accommodation sleeps 13 guests and features four bedrooms, including two with bunk beds, a game room, three decks, internet, and air conditioning, with proximity to Rod n Reel Charter Fishing and Franklin Point State Park.
This accommodation sleeps 13 guests and features four bedrooms, including two with bunk beds, a game room, three decks, internet, and air conditioning, with proximity to Rod n Reel Charter Fishing and Franklin Point State Park.

North Beach, Chesapeake Beach
10/13 – 10/15
$300/nighttotal: $600 (2 )
The Blue Crab Beach House - Free Beach Passes
2 1apartment , North Beach
This North Beach vacation home boasts an excellent location, just within two miles of Chesapeake Beach Water Park, the Bayside History Museum, Rod n' Reel Charter Fishing, and 1.6 miles from the Chesapeake Beach Railway Museum.
This 800-square-foot seaside rental sleeps six guests comfortably, offering two bedrooms, two bathrooms, a fully equipped kitchen, a private fenced yard, a swimming pool, a spa, and free Wi-Fi.
This 800-square-foot seaside rental sleeps six guests comfortably, offering two bedrooms, two bathrooms, a fully equipped kitchen, a private fenced yard, a swimming pool, a spa, and free Wi-Fi.









