Holiday 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 favourite

Home in Chesapeake City

4.91 out of 5 average rating, 87 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 favourite

Home in Chesapeake City

4.91 out of 5 average rating, 55 reviews

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.

Guest favourite

Apartment 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

4.8 out of 5 average rating, 25 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 favourite

Guest house in Elkton

4.99 out of 5 average rating, 77 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 favourite

Home in Elkton

5 out of 5 average rating, 8 reviews

Breathtaking Waterfront w/pool - Winter quietness!

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 and 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 are open. Closed Oct- mid May

Guest favourite

Home in Warwick

5 out of 5 average rating, 6 reviews

Saybrook Hall | Pickleball + Pool + Hot Tub

BNB Breeze Presents: Saybrook Hall! Discover the perfect getaway in this spacious rental home in Maryland, and stay in a real life colonial home! The original house sat in Connecticut and was disassembled to be built into a newer modern version here in Warwick, MD. Featuring a charming rustic design with wooden beams and cozy accents, this home seamlessly blends traditional warmth with modern amenities. - Pickleball/basketball Court - Pool - Hot Tub - Chipping Green - Pizza Oven

Home in Elkton

4.92 out of 5 average rating, 122 reviews

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

Guest favourite

Guest house in Elk Mills

4.97 out of 5 average rating, 98 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.

Superhost

Apartment 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 favourite

Guest house in Elkton

4.92 out of 5 average rating, 25 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 favourite

Home in North East

5 out of 5 average rating, 111 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.