Holiday rentals in Chesapeake City

Modish Cottage w/Bar Shed Charm!

Welcome to your perfect getaway in the heart of historic Chesapeake City! Just steps away from local restaurants, nightlife, boutique shops and scenic canal views, you'll love exploring all this waterfront town has to offer. Inside, a stylish retreat for relaxing. But the real gem...the back yard. Kick back with a drink at the bar shed, grill a meal, and gather around the fire pit to relax under the stars. Don't forget your bike (for the bike trail) or kayak for the more adventurous at heart!

hygge haven: hygge= happy + cozy

Chesapeake City is a historic town located on the C & D Canal; it's not unusual to be greeted by locals as you explore the town. The apartment is a bedroom with sitting area, fully equipped kitchen & bath. It's in the heart of the town & walkable to all the boutiques, restaurants & nightlife! It comes equipped with a Nespresso machine, coffee pods,sparkling water, wifi & tv if you just want to chill. It's steps from the canal for lovely sunrise/sunsets! There are bike/walking paths nearby.

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and a PERFECT spot for a romantic couples getaway! honeymoon/celebrations Designed with that in mind, it has a hot tub,kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed,a chandelier & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity,a large soaking tub,a tile shower with a soothing 3 function rain shower, is complete with luxury linens, cozy robes & soft towels

Private Country Guesthouse Getaway Minutes from UD

Come stay at this relaxing private getaway! Located 10 minutes from the University of Delaware and tax-free Delaware shopping, 5 minutes from the breathtaking Fair Hill State Park and Milburn Orchards. The guesthouse is completely private, boasting a front deck and back deck surrounded by nature. The living room, bedroom, bathroom, and convenient kitchen are completely private. As a guest, you'll have the privilege of accessing the pool, which is exclusively reserved for you.

Countryside-Stable House-Open Studio-Quiet for 2

Get out of the city and stay here. 3+ acre historic Fair Hill horse farm and 590 sq. ft. stable house! Minutes from trails, wineries, orchards, golfing, and scenic small towns! Highlights - Newly renovated! - No checkout chores! - Traditional farmhouse sink - Dine in the garden - Roku TV: Netflix, Hulu - Stables: 6 stalls & 2 paddocks available Lowlights - Two narrow interior doorways - Kitchen minus a conventional oven. A mini-oven/air fryer, microwave, & hotplate provided

Cottage Just Off North East's Main Street

Our cozy cottage is located just off Main Street in North East, an easy walk to restaurants, shops and pubs. The cathedral ceilings and exposed rafters create an unexpectedly dramatic space you will find warm and inviting. The relaxing back deck looks down toward a creek that flows through the neighboring property. Our cottage is the perfect place to stay when you're on the road for work, or a romantic weekend (or mid-week) getaway.

The River Cottage

Take it easy in this unique cottage built in the 1800s nestled upon the Granite Cliffs of Port Deposit Maryland. While enjoying your tranquil get away you’re minutes from local shops, local dining, local wineries, local breweries and a local marina. There is plenty of sightseeing and wildlife. If you enjoy fishing and kayaking it’s just a short distance away.

Sunset Dome Rustic Camping | King Bed | Small Farm

Enjoy a restorative and Earth-friendly camping experience situated on our quiet farm. Relax by the campfire with your partner or close friend and craft a delicious meal with the cooking essentials provided by us. Don't sweat the packing, simply bring a cooler, firewood (if desired) and clothes and prepare to enjoy yourself on this little farm oasis.

Pyle Cottage, circa 1750

Relax at this unique and tranquil getaway located within 5 minutes of Fair Hill Training Center and MD 5* Event site. Quiet with lots of outside spaces and local hiking & biking right out your front door. Ten minutes off Rte 95 ~ 1 hour south of Philadelphia and 1 hr north of Baltimore in the tristate corner of DE-MD-PA.