Vacation rentals with a pool in Cecil County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Cecil County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Chesapeake City

4.9 out of 5 average rating, 83 reviews

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!

Guest favorite

Condo in Betterton

4.91 out of 5 average rating, 23 reviews

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.

Home in Elkton

4.79 out of 5 average rating, 24 reviews

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.

Guest favorite

Home in Earleville

4.9 out of 5 average rating, 39 reviews

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. )

Guest favorite

Guesthouse in Elkton

4.99 out of 5 average rating, 71 reviews

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.

Guest favorite

Guesthouse in Elk Mills

4.96 out of 5 average rating, 82 reviews

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.

Home in Elkton

5 out of 5 average rating, 3 reviews

Breathtaking Waterfront w/pool - Fall dates avail.

The incredible 4-bedroom, 2-bathroom 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 or fishing gear. You can 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 pool are open.

Superhost

Condo in Betterton

4.92 out of 5 average rating, 36 reviews

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.

Guest favorite

Guesthouse in Elkton

4.92 out of 5 average rating, 24 reviews

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.

Guest favorite

Home in North East

5 out of 5 average rating, 108 reviews

*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.

Tiny home in North East

4.72 out of 5 average rating, 83 reviews

Cozy Log Cabin on the Bay at Sandy Cove

Tiny Home Nestled in the woods, this 600 sq ft, Conestoga Log Cabin is cozy & rustic, yet meets all of your needs. Sleeps 6-8 - Bedroom w/ a double bed - Bedroom w/ bunk beds - Open loft w/ 2 single beds - Living area with a futon - Kitchenette - Dining area - WiFi and a smart TV Stunning Location Sandy Cove is a Christian retreat center with 200+ acres on the headwaters of the Chesapeake Bay, offering beautiful views in all seasons.

Guest favorite

Rental unit in Betterton

5 out of 5 average rating, 15 reviews

Bayside Bungalow

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 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.