Vacation rentals with a pool in Cecil County

The Mint Cottage in Chesapeake City

The Mint Cottage is new to the air bnb market. It is a 3 bedroom Cape Cod on .5 acre lot in Charming Chesapeake City! The 1st floor features a master bedroom suite with updated amenities, large living room and kitchen, PLUS a full hair and makeup station (great for bridal parties). The 2nd floor has two bedrooms- a queen and 2 twin beds. The house features 3 full baths.The back yard has a private swimming pool, fire pit and patio. Terrific location to walk to waterfront, shops, and restaurants!

Breathtaking Waterfront - Christmas on the Water!

2027 Christmas is still available. Now booking for summer 2027. Serenity House in an incredible 4-bed 2-bath waterfront home - The ultimate getaway! Pool/Spa are Seasonal **open mid May through Sept only** Pool and hot tub are **closed Oct - May** We do not have a separate stand alone hot tub. Featuring a fixed boat dock and a floating dock, you can easily bring your boat (up to 21 feet with/ docking fee) Enjoy a variety of water sports, including the provided kayaks (4) and paddle boards (2)

Pool Open 4/1 to 10/31! Hot tub open all year!

Best experience on the upper Chesapeake Bay (Elk River). 1st floor has 3 ensuite bedrooms. Large kitchen with breakfast bar all with water views, granite counters, beer tap, wine cooler& ice maker. Dining room with water views. Large living room and river room with expansive water views. 2nd level has 2 bedrooms - a queen&single. Large heated swimming pool (seasonal) Year-round Hot tub. 2 Fire Pits Riverside deck. Long dock for fishing & mooring whips for your boat. Beautifully landscaped.

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Best kept secret beach-condo on the Chesapeake Bay

Beach. Pool. Sunrise and Sunset. Condo with fantastic view of calm water Betterton Beach. Beach less than 100 steps from front door, with public boat ramp, pier, & bath house. Historic Chestertown (culinary hub w/cute shops) is 15 minutes away. Thoughtfully equipped condo is a great place for families or couples to relax and unwind. Kitchen outfitted for those who like to cook. Public slips (permit required) & pier where you can fish & crab. Beach gear provided. Playground close by.

Chesapeake Waterfront Private Pool

Welcome to our beautiful vacation rental, located on the water. Inside, you'll find an inviting open floor plan, with water views. Outside, you'll find a private oasis, with a large deck overlooking the water and a sparkling pool. The pool is great for cooling off on hot summer days. Note: our dock is currently out of service due to tree damage, and water is too shallow for boats. Our home has been totally renovated and is well-maintained, so you'll have a comfortable and enjoyable stay.

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.

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

At 3 minutes walk to the beach, this Bayfront condo perched on a bluff in beautiful Betterton is a gem the whole year through. Two level loft condo with three bedrooms (2 BR downstairs, 1 BR upstairs) as well as an ADDITIONAL sleeping loft with two single beds. Two big decks supply scenery for outdoor meals and gatherings. Come for a stay, your cares melt away. The word “peaceful” does not quite do it justice. See for yourself how calm and relaxing life can be.

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Historic Victorian Walkability Chesapeake City

The Ultimate In-Town Retreat: Modern Luxury Meets Historic Charm: Step into a world of elegance in the heart of Historic Chesapeake City. This beautifully renovated 5-bedroom, 4-bathroom estate has been professionally decorated to offer a seamless blend of modern luxury and classic Maryland charm. Whether you are hosting a family reunion or a sophisticated getaway with friends, this home is your private sanctuary just steps from the best the town has to offer.

Thomas Ricketts Carriage House

The Thomas Ricketts Carriage House is an upscale, private retreat on a 33 acre historic working estate in the heart of Cecil County, Maryland. Ricketts House is conveniently located just minutes from I-95 and all of the attractions Maryland, Delaware and Southeastern Pennsylvania have to offer. It is the perfect balance between a central location and privacy, between the bustle of big cities and college towns, and the quiet of unspoiled nature.

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Spacious family home w/pool, sauna & hot tub

Experience a spacious family retreat with pool, sauna, and private in‑law suite. - 5 bedrooms • 4 full baths • King & queen beds - Outdoor pool, hot tub & sauna for relaxation - Deck with outdoor TV overlooking fenced backyard & horse meadows - Garage game room, gym equipment & laundry for convenience - In‑law suite w/ kitchen, king bedroom & private entrance (stairs) - Fully stocked kitchen & coffee bar for easy meals

Beach Haven Hideaway ~ stunning water views!

We are a small enclave of condos, perched high on a bluff, overlooking the Chesapeake Bay. From the deck you have wonderful views of the beach and the best Bay sunsets! We are no more than 100 steps to the beach, where you have a picnic pavilion, beach volleyball, and picnic tables. This is the perfect getaway for small families or couples.

Private retreat with Pool - Close to wedding venue

Private house with wraparound deck overlooking a pool and open meadow surrounded by a forest. Enjoy your quiet time listening to birds or watching wildlife or take a swim! The property is close to the Bohemia Overlook wedding venue.