Vacation rentals with a pool in Cecil County

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.

Breathtaking Waterfront Now booking Fall 2025

Summer 2025 almost full! 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), jet ski and fishing gear. Enjoy a variety of water sports, including the provided kayaks (5) and paddle boards (2), or simply relax on the peaceful deck that spans the back of the home. May-September is when the private saltwater pool and jacuzzi are open. Closed Oct- mid May

Waterfront Estate with Pool on 16 acres

Looking for a place to enjoy a water front estate on 16 acres of land? Look no further than Cherry Grove Manor. It is a traditional style home that sleeps 18 & features 6,000 sq. ft. on 3 levels of living. Enjoy your private 550 ft. sandy beach that overlooks the mouth of the Elk River with views into the Chesapeake Bay. There is a private dock that you can fish and crab from. The newly renovated Salt Water Pool (not heated) offers views of the water. (Pool available May-September. )

Spacious Wing of Rustic Farmhome

This private addition to the main farmhouse has 3 levels and a fireplace. With 3 bedrooms and multiple sleeping arrangements, this space makes for a great getaway with friends and family. This horse farm has an outdoor seating area equipped with a grill, fire pit, and pool. The owner is a registered massage practitioner with her practice in a quaint cabin on-site. The property has a gated entrance and room for parking. Within 10min to Fair Hill Nature Preserve and 20min to Newark DE.

Farmhouse with large in-ground pool and river view

This house surrounded by fields and gardens, has lots of light, a fully equipped country kitchen, large pool , farm setting and river views. The large living room has wood floors and beautiful views. There are three bedrooms . Relax in our Finnish sauna or, in the summer months, jump into the large in-ground pool. The yard and grounds have plenty of places for kids to play.; we do not allow parties, events or gatherings nor outside music. no smoking inside. WiFi is available

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.

*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.