
House vacation rentals in Chesapeake City
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Top-rated house rentals in Chesapeake City
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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 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. Relax, visit, enjoy each other NO TV's

Cozy 3-bedroom home w/ Hot tub & firepit
This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

Historic J. Pyle House Main St Location Pets OK!
The J. Pyle House, built in 1844, is in the National Historic District of Kennett Square, PA. We are in the heart of walkable downtown Kennett Square and a quick 6 minute drive to Longwood Gardens. The townhome has been lovingly restored to reflect its mid-19th century roots, while providing an updated, cozy place to relax while visiting our quaint town. 45 min to the PHL airport, 25 min to Wilmington, DE, 25 min to West Chester University, 6 min to Longwood Gardens 15 min to Winterthur

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.

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.

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.

2 BR/1 BA/Office University of DE
Home of the fighting Blue Hens and the University of Delaware, Newark is centrally located to Philadelphia, Baltimore and surrounded by over 12,000 acres of beautiful parkland. Enjoy this recently renovated home with spacious rooms, a fully equipped kitchen and laundry and plenty of off-street parking. Every detail has been thought of for your comfort including free WIFI. Great for UD Events, Weddings, Anniversaries, Car Shows, Mountain Biking and Cycling Weekends, and more.

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 back door 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.
Popular amenities for Chesapeake City house rentals
House rentals with a pool

Creek front home *heated pool open year round!*

Waterfront Winter on the river 2025/26 available!

Cording Lodge*Pool*Pickleball/Basketball court

Sweet home w/pool & woods at peaceful Glen Mills

The Hidden Gem•Heated pool•Pickleball Court

Spacious 4-bedroom house with a private pool.

The Peaceful Getaway (with private pool & hot tub)

The Waterfront Retreat- *With Sauna and Hot Tub!*
Weekly house rentals

Connection Pointe•River views•Quiet•Peaceful

Spacious 3BR/2BA near UD/Christiana Care Hospital

HOOK WINE & SINKER sleeps 14 w/ Boat Slip at Inn

The Cooper House in Charlestown, MD

Newly built Tiny House in Historic Kennett Square

Ruby's Sea Glass Cottage near Betterton Beach

Charming, updated home in Historic Chesapeake City

Wister Loft: Charm & History with Modern Love.
Private house rentals

Grandma’s Cottage

The Sunset House

Riverfront Haven @ Hances Point

The Lighthouse

Chesapeake Waterfront Vacation Rental with Dock

Spacious, Quiet & Peaceful

Two bedroom small ranch with beautiful forest view

Lark's Nest on the Chester River
Quick stats about house rentals in Chesapeake City

Total vacation rentals
Explore 10 vacation rentals in Chesapeake City

Nightly prices starting at
Chesapeake City vacation rentals start at $224 CAD per night before taxes and fees

Verified guest reviews
Over 650 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Chesapeake City vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chesapeake City rentals

5 Average rating
Chesapeake City stays are highly rated by guests—averaging 5 out of 5!
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