Holiday rentals with a pool in Cecil County

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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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Top guest favourite
A cozy living area features a dark brown leather sectional sofa facing a 55” HDTV. A round table with fresh flowers is positioned near the sliding glass doors, which provide natural light and a view of the outdoor patio. Light-colored dining chairs are arranged around a wooden dining table.
Flat in Chadds Ford
4.91 out of 5 average rating, 281 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”. Amazing! Ask about guest passes to the Gardens w/2 night stays. Winterthur, Brandywine River Museum, Wineries & more 3 Bedrms, 4 beds Beautiful lg bathrm & Powder room Dining/TV rm Kitchen: Convection oven, Cooktop, Microwave, Keurig coffee maker WiFi, 55” HDTV Full size washer, dryer, refrigerator Gentle Pets welcome! *No Smoking, No Parties

Top guest favourite
A welcoming entrance is flanked by lush greenery and trees, leading to a charming house with a red brick pathway. The landscape features a stone border and a central fountain, creating an inviting atmosphere for guests.
Guest suite in West Chester
5 out of 5 average rating, 195 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 favourite
Two dogs sit on a grassy lawn, showcasing a peaceful evening scene. The background features a picturesque view of farmland and a charming house with a well-maintained yard. The sky is painted in soft pastel colors, indicating sunset.
Guest suite in Oxford
4.9 out of 5 average rating, 136 reviews

Cozy country stay getaway that's pet allowed!

Large solar heated pool for summer fun! Relax and enjoy the peaceful surroundings on one acre at the end of a cul-de-sac. Pet allowed large property with room for everyone to stretch their legs. Private space all to yourself, with parking and seperate 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.

Top guest favourite
A spacious lawn is surrounded by tall trees, leading to a two-story house with a porch. Soft evening light casts a gentle glow, while a hammock can be seen suspended between two trees, inviting relaxation in the outdoor space.
Casa particular in Chestertown
4.93 out of 5 average rating, 166 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 favourite
The living room features a high, wooden ceiling with large windows allowing natural light to fill the space. A comfortable arrangement of sofas and chairs offers ample seating, complemented by a stylish area rug. A modern fireplace adds warmth to the inviting design.
Home in Perry Hall
4.99 out of 5 average rating, 114 reviews

Gunpowder Retreat

Unwind and relax with friends & family at this peaceful mid-century modern home. Nestled along the Gunpowder Falls State Park you can enjoy long summer days lounging in the pool under a canopy of trees or take an adventure along the hiking trails easily accessible from the back yard. Although there is no reason to leave this oasis, shopping and restaurants are only a five-minute drive away. Enjoy the beauty of nature without giving up modern comforts in this 4 bedroom, 3 bath home.

Top guest favourite
The exterior of a single-story, stone-faced house is showcased, surrounded by a well-manicured lawn. Lush greenery and flowering plants are visible, while a pathway leads to the inviting entrance. Large windows allow for natural light to enter, enhancing the home's welcoming appearance.
Guest suite in Parkville
4.96 out of 5 average rating, 223 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

Top guest favourite
A private deck is presented with woven seating arrangements, including a unique hanging chair and a sofa. A round table is placed at the center, surrounded by natural greenery. The wooden flooring and patterned rug enhance the outdoor relaxation space.
Guest house in Elk Mills
4.98 out of 5 average rating, 146 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.

Top guest favourite
A stylish swing chair with turquoise cushions is suspended in a bright living area. A round wooden coffee table occupies the center, adorned with a vase of fresh flowers and a decorative figurine. Large windows with sheer curtains allow natural light to enter the space.
Flat in Baltimore
4.95 out of 5 average rating, 137 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.

Top guest favourite
The front entrance of the home features a well-maintained pathway bordered by lush greenery and flowering plants. An elegant lamp post stands beside the path, illuminating the approach to the entrance where double doors and a decorative American flag are positioned.
Flat in Chadds Ford
5 out of 5 average rating, 222 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 favourite
An inviting living space is highlighted by warm wood flooring and a cozy leather sofa. Framed artwork adorns the walls, while a dining table and green accent piece provide unique touches. Natural light illuminates the area, and a staircase leads to the upper level.
Townhouse in Baltimore
4.91 out of 5 average rating, 139 reviews

Cozy, Cute and Clean rowhouse w/ 2 Masters!

Welcome to Baltimore! My house has everything you will need for your short or long term visit. It’s walking distance to John's Hopkins hospital, Patterson Park( beauty, tennis courts, basketball courts, good place for running or biking). The house is also very close to Fells Point, Canton ,a $10 Uber to Camden yards and $15 to M&T. I have lots of small kind of useless appliances like a waffle maker and juicer, if you’re into that sort of thing.

Guest favourite
A serene outdoor patio features a heated inground pool, accentuated by a gentle waterfall. Comfortable lounge chairs are positioned around the pool, while a large rock formation adds a natural element to the space. Lush greenery is visible in the background.
Home in Peach Bottom
4.96 out of 5 average rating, 114 reviews

Creek front home *heated pool open year round!*

Welcome to Quiet Brook Oasis Treat yourself to a relaxing weekend in this beautiful secluded creekfront home nestled in the woods that has a private inground pool, with a waterfall opened and heated all year. Located in peaceful Amish country, southern Lancaster county this newly remodeled home is sure to offer a relaxing and peaceful getaway. This is a perfect retreat for family or a couples romantic weekend. Find us on social media!

Superhost
A two-story home is shown with a light brown exterior and green shutters. A front porch features a railing and seasonal decorations. Stone steps lead to the entrance, surrounded by well-maintained grass and a neatly trimmed evergreen shrub.
Flat in Nottingham
4.86 out of 5 average rating, 147 reviews

Bright and Cozy 2nd floor apt

My place is within walking distance of restaurants and family-friendly activities, within minutes of White Marsh Mall, easy freeway access for going to an Orioles/Ravens game, and the Inner Harbor or just hike a neighborhood trail. You’ll love my place because of Connivence to everything, in a quiet friendly neighborhood and private entrance. My place is good for couples, solo adventurers, business travelers, and families (with kids).

Popular amenities for Cecil County rentals with a pool