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

Guest suite in Oxford

4.91 out of 5 average rating, 102 reviews

Private, pet allowed quiet country oasis stay

Relax and enjoy the peaceful surroundings on one acre and nestled at the end of a cul-de-sac, with a farm and treeline view. Pet allowed and good to accommodate a short visit. Private space, parking and entrance. AC, queen bed, foldout couch, microwave, Keurig coffee, mini stove and mini fridge. There is a bathroom with necessary toiletries, sink and large walk in shower. Amish style sticky bun, fruit and juice will be provided for breakfast. Need a restaurant suggestion? Check the "Guidebook"

Guest favorite

Rental unit in Chadds Ford

4.91 out of 5 average rating, 234 reviews

Spacious & Peaceful, Pvt, 3mi Longwood Gardens

Comfy & Spacious Private Downstairs Suite in 2 acres of nature Private Pool Heated end of May to Sept 3 mi to Longwood Gardens aka “America’s Versailles”. Always Amazing! Ask about guest passes avail with 2+ night stays. Winterthur, Brandywine River Museum, Wineries & more 3 Bedrms, 4 beds Beautiful large bathrm Dining/TV rm Kitchenette: Convection oven, Microwave, Keurig coffee maker, Electric fry pan WiFi, 55” HDTV Full size washer, dryer, refrig Gentle Pets welcome! **No Smoking, No Parties

Guest favorite

Guest suite in West Chester

5 out of 5 average rating, 183 reviews

Spacious Studio Suite 4 miles to Longwood Gardens

As you come down the long private drive, you will be reminded that you are staying in one of most coveted areas of Chester County. Pictured is the main house which we reside in. Both grand & relaxing, you will be staying in the 1500 sq. ft. private walk-out open-concept studio with wine cellar bedroom, pool table, dedicated playroom & granite island. Sitting on 12.9 park-like acres every view is private with your own private pool. So tranquil yet just minutes away to Longwood Gardens and more.

Guest favorite

Casa particular in Chestertown

4.94 out of 5 average rating, 133 reviews

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

Guest favorite

Guesthouse in Elkton

4.99 out of 5 average rating, 74 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

Guest suite in Parkville

4.95 out of 5 average rating, 207 reviews

A home away from home

This spacious 2 bedroom apartment is located in a lovely, safe suburban neighborhood. Guest will enjoy the lovely garden setting and patio. Only a short drive to The Inner Harbor, Annapolis, Camden Yards, M&T Bank Stadium,Johns Hopkins, just to name a few. Guests will definitely feel right at home with free wi fi ,HBO and Showtime. We are a retired couple who reside in the upper level of this house. The apartment is spacious and completely private with a well appointed full kitchen

Guest favorite

Guesthouse in Elk Mills

4.97 out of 5 average rating, 89 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.

Guest favorite

Guest suite in Baltimore

4.95 out of 5 average rating, 116 reviews

Patterson Park Penthouse with Rooftop Deck!

Located overlooking the lovely Patterson Park and close to Canton & Fells Point this is a great spot for a Baltimore visit! This large and newly renovated Baltimore rowhouse less than 10 min from the Inner Harbor, Johns Hopkins main campus, Bayview, Fells Point, Canton. We invite you to stay in a lovely private apartment oasis on the top floor of the row house that has stunning views of the park and access to a balcony and large rooftop deck for lounging or dining.

Guest favorite

Serviced apartment in Chadds Ford

4.99 out of 5 average rating, 124 reviews

Silo Suite

Welcome to our charming suite located in the heart of the historic Brandywine Valley. Nestled within the entrance of a beautifully converted 12,000 square foot barn home, this space offers a truly unique and memorable stay. Our special place is perfectly situated between the renowned Brandywine River Museum and the Chadds Ford Winery, and in just minutes, you can explore the enchanting beauty of Longwood Gardens or dive into the world of history at Winterthur.

Guest favorite

Home in North East

5 out of 5 average rating, 110 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.

Guest favorite

Guesthouse in White Hall

5 out of 5 average rating, 111 reviews

Dragon In My Cabin By The Pool Jacuzzi and Sauna

(NO PARTIES, MAX AMOUNT OF PEOPLE ON PROPERTY IS 4) Make lasting memories with a unique experience in our dragon themed cabin. Enjoy lounging by the pool. Relaxing in the spa and sauna. Cookout on a full size wood grill or gas grille with access to the outdoor grilling area. Play your type of music with our pool surround sound system. Or get in some out doors recreation with the horse shoe pit, soccer field and basketball court.

Guest favorite

Home in Conestoga

4.91 out of 5 average rating, 176 reviews

3-bedroom house in quiet area bordering park

This beautiful property in Conestoga, PA borders Silver Mine Park which has a creek, soccer and baseball fields, and hiking trails. Located 10-15 minutes from Lancaster City, ~20 minutes from many popular (Amish-related) tourist attractions, ~10 minutes from the Pequea boat launch, and ~18 minutes from the Pinnacle Overlook this is the perfect property either for an action-packed vacation or a peaceful, relaxing one.