House holiday rentals in Chesapeake City

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Top-rated house rentals in Chesapeake City

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Guest favourite

Home in Lancaster

4.99 out of 5 average rating, 358 reviews

2 Blocks from City Square + Skyline view 🌆

LOCATION + LUXURY = Comfortable Living! Jefferson House is located in the heart of historic downtown Lancaster—only 2.5 blocks from City Square. Tucked in a quiet alley yet steps from the action, you can walk to Lancaster’s best restaurants, markets, coffee shops, & more—all in minutes. We try really hard to make your stay as special as possible. Our priorities are as follows: #1) CLEAN — Beds, Bathroom, etc = Spotless! #2) Communication — Always there for you! #3) Convenience — Fully stocked

Top guest favourite

Home in Shady Side

5 out of 5 average rating, 171 reviews

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. Set along the Chesapeake, it offers front-row seats to breathtaking sunsets—where golden light dances across the water. Inside, Nordic-inspired design meets quiet luxury, featuring award-winning mattresses and bedding that promise restorative sleep. Here, time slows, and luxury isn’t just something you see—it’s something you feel. We invite you to read the reviews of so many happy guests.

Top guest favourite

Home in Perryville

4.99 out of 5 average rating, 122 reviews

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!

Guest favourite

Home in North East

4.96 out of 5 average rating, 113 reviews

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.

Guest favourite

Home in Aberdeen

4.95 out of 5 average rating, 179 reviews

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.

Guest favourite

Home in North East

4.94 out of 5 average rating, 124 reviews

Historic Creekside Home - 2br 2.5ba Downtown

Built in 1875, this newly renovated two bedroom home, is centrally located in downtown North East. Modern finishes and an open concept living space compliment the original wood floors, clawfoot tub and exposed brick walls. All the amenities of Main Street are steps away, yet the home is tucked away on a quiet street with a creek in the back yard. Our home is 2.5 miles from I-95 and one block from North East Community Park, Anchor Marina and the headwaters of the Chesapeake Bay.

Guest favourite

Home in Elkton

4.96 out of 5 average rating, 145 reviews

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.

Guest favourite

Home in Elkton

4.83 out of 5 average rating, 366 reviews

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.

Guest favourite

Home in Perryville

4.93 out of 5 average rating, 218 reviews

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.

Superhost

Home in Newark

4.82 out of 5 average rating, 112 reviews

Welcome to The Richfield!

Just minutes from U of D and the Bob Carpenter Center, tax free shopping at the Christiana Mall, and scenic walks at Rittenhouse park. A perfect oasis for the whole family to enjoy with a touch of sophistication for any business trip. Enjoy 2 floors of entertainment space with 2 50' TVs, Foosball Table, and a Dartboard to pass the time. A coffee bar will help kick start your day, while the complementary bottle of wine will help you relax at the end.

Guest favourite

Home in Earleville

4.92 out of 5 average rating, 169 reviews

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.

Top guest favourite

Home in North East

5 out of 5 average rating, 112 reviews

*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.