House holiday rentals in Chesapeake City

Upper Chesapeake Getaway

Come relax with expansive views of the Upper Chesapeake with family or friends. Tucked away in Carpenter's point, you'll find peace watching boats pass by and local wildlife. The newly renovated home features newly 3BR, 1.5 Bath with a fully functional kitchen. You'll enjoy the beautiful sunrise views, water access, kayaks and deck. Local amenities include Great Wolf Water Park, Elk Neck State Park, local restaurants, and Perryville Casino. We welcome you to join the relaxing experience!

Red Point Lighthouse

Recently updated unique lighthouse replica on the northern tip of the Chesapeake Bay. 4 bedrooms & 2 sleeping nooks, the house can sleep up to 14 in 6 beds (3 kings, 1 queen, 2 doubles) and one queen sofa bed. 4 bathrooms - 2 ensuite. Two living rooms, fully equipped kitchen, family style dining area. Wrap around decks on multiple floors. Firepit, Adirondack seating, lawn games for enjoying 1.5 acres with water views. Community sandy beach across the street for strolling & relaxing.

Tranquil Carriage House*MCM *Country *Wildlife

The Aberdeen Carriage House is in a country setting with a country road. We are near city limits and have most of your needs right here. You have a grocery store, dollar store, Target, Walgreens, Planet Fitness, and restaurants in five minutes. Historic Havre de Grace, Ripken Stadium, Vineyards, Boating, and Golfing, only ten minutes. Baltimore and Stadiums are only 35 minutes down I95. The house is spotless and fully loaded with all the comforts of home—pet and chemical-free space.

Appleton Retreat

This 3 bedroom, 2 bathroom home is the perfect place to get away from it all while remaining convenient to all the best that Maryland, Delaware, and Pennsylvania have to offer. Minutes from Fair Hill Natural Resource Management Area for the horseback riders, mountain bikers, hikers and nature enthusiasts. University of Delaware is a quick 10 minute ride away to catch a football game or celebrate commencement. Other local attractions - boating, fishing, vineyards and breweries.

Cozy Cottage Elkton North East 3bed 2 bath Patio

Hacienda on the Hill! Perfect country & city location! Close to North East activities, fishing tournaments & shows. Newark & UofDE(20min). Sandy Cove & North Bay(20 min). Quiet, end of gravel road location. Offering 3 bedrooms 2 full baths & stocked kitchen. Backyard patio t w/seating, & fire pit. The best part, just 1 mile to quaint downtown North East with free parking!! 1 mile from seafood, mexican, steak house, coffee shops, grocer, convenience store etc.

Top of the Chesapeake - Private Waterfront Home

Our house is nestled between the shore of the NE River and the creek and marsh directly behind. The home is warm, unassuming and inviting; you'll feel right at home. Perfect for familes or groups, or a romantic weekend. Bird watchers will love the bald eagles, ospreys, kingfishers, mallards and cormorants, to name a few. The upstairs living room is a perfect place for the kids while the adults enjoy the lower area. You find our place warm, cozy and quiet.

Beachfront Sunsets on the Water at Oakwood Beach

You’ll instantly relax when you arrive at this private beachfront home on the beautiful Delaware River (2020 River of the year!). This hidden gem is off the beaten path, making it perfect for you to escape the hustle and bustle of your busy day-to-day. You’ll love the amazing sunsets and water fun — walk out the backdoor directly onto the large deck and sandy beach. Message us for information about the local wineries and distilleries or for kayaking!

Cozy 4 BR 3 BA Near Chesapeake City

Peaceful, cozy modern cottage with many amenities in a water-oriented community along the Bohemia River. Just minutes from Chesapeake City and located across the street from the water. Our house is perfect for family vacations, tranquil retreats, girl/guy getaways, weddings, wedding guests. Two queen master BR’s w/private baths on the first floor, second floor has one larger BR w/twins and smaller BR w/daybed +trundle and shared bathroom.

*SHELTER COVE * 3BR home by 2 marinas * Boat Slip*

Between 2 marinas, Shelter Cove is a rancher with an in-ground pool (open from May until September) Spend time on the North East River or exploring the local shops museums and wineries. You can unwind beside the cozy fireplace in the DR, or sit out on the deck. Each of the 3 BRs has a full bath, TV, & individual climate control for your comfort. There is room to park your boat, or dock it in the slip provided at the marina down the road.