Holiday 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!

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.

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 Retreat W/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, and our private dock is a great spot for fishing or just enjoying the scenery. Our home has been totally renovated and is well-maintained, so you can be sure that you'll have a comfortable and enjoyable stay.

Waterfront Winter on the river 2025/26 available!

Now Booking winter and Summer 2026 the summer is going quick! The incredible 4-bed 2-bath water-facing home is the ultimate getaway Featuring a fixed boat dock and a floating dock, you can easily bring your boat (up to 21 feet with a $125 docking fee) Enjoy a variety of water sports, including the provided kayaks (4) and paddle boards (2) Pool/Spa are Seasonal **open mid May through Sept only** Pool and hot tub are **closed Oct - mid May** We do not have a separate stand alone hot tub

Historic Victorian Queen Chesapeake City

Welcome to your perfect getaway! This beautifully renovated and professionally decorated 5-bedroom, 4-bathroom home combines modern luxury with classic charm — all just steps from town. Enjoy the gourmet kitchen. Outside, unwind by the private in-ground pool, soak in the hot tub, or sip your morning coffee on the screened-in porch. Located in-town and walking distance to shops, restaurants, local boat docks, and fun. You’ll love the convenience and charm of this unbeatable location.

Woodland Retreat at Fair Hill-Relax and Recharge

Welcome to our luxurious 6-bedroom, 4.5-bath home nestled on 12 acres of woodlands with expansive farmland views. Ideal for families, corporate retreats, or large groups. The home features a luxurious pool, hot tub, sport court feat. a full pickleball court, golf driving net, bikes, and a gourmet kitchen. Inside, enjoy a sauna, home gym, steam shower, and a designated meeting area. Relax by the fire pit or explore the stream and woods. A perfect destination to relax, work, and unwind.

Historic Mansion - The Anchorage

The Anchorage is the perfect property for groups, big or small, to escape the hustle and bustle and enjoy our serene setting with breathtaking views of endless farmland. Nestled between Georgetown, MD, Chesapeake City, MD & Middletown, DE there is plenty to offer in terms of food, entertainment and activities! Come stay with us! :) Private Pool May-Sept 11 bedrooms; 10 1/2 baths **MUST BE OVER 25 TO RENT -- do NOT send if age requirement not met *No Parties - No Weddings/Events

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.

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.

Beach Haven Hideout

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 BBQ area with communal grills and picnic tables. This is the perfect getaway for small families or couples.