Vacation 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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Guest favorite

Apartment in Chadds Ford

4.93 out of 5 average rating, 201 reviews

Spacious & Peaceful, Pvt Pool-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

Home in Oxford

4.89 out of 5 average rating, 45 reviews

Roomy pet allowed country oasis & saltwater pool

More guests upon request. Pet allowed space on over one acre, with lots of room and a pool! Property is shared-host occupies 1st floor. You will have a large private living area that opens to a porch including; spacious family room, streaming service w/42" tv with surround & large sectional couch. Wet bar area with a sink, fridge, mini-oven, hotplates, and dishes/silverware. Large bathroom with double sink, tub and stand up shower. Amish style sticky bread, juice & fruit served for breakfast.

Guest favorite

Casa particular in Chestertown

4.93 out of 5 average rating, 103 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

Guest suite in West Chester

5.0 out of 5 average rating, 161 reviews

Tranquil, Picturesque - 4 miles to LongwoodGardens

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. Both grand & relaxing, you will be staying in the 1500 sq. ft. gorgeous private walk-out lower level with 2 bedrooms, wine cellar dining, pool table & 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, historical sites, bars & wineries.

Guest favorite

Guesthouse in Elkton

4.98 out of 5 average rating, 54 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

4.96 out of 5 average rating, 190 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

4.98 out of 5 average rating, 42 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

Home in North East

5.0 out of 5 average rating, 96 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 the 1st week in May until the last week in 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

Apartment in Chadds Ford

4.98 out of 5 average rating, 59 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

Guesthouse in Elkton

4.92 out of 5 average rating, 12 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 Conestoga

4.92 out of 5 average rating, 145 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.

Guest favorite

Home in Strasburg

4.93 out of 5 average rating, 116 reviews

Findley Farm View Cottage (Outdoor Pool!)

Designed to be a quaint farmhouse getaway set in the middle of Amish country. Close to Sight and Sound Theater! Very easy to get to and close to many amenities, attractions, and destinations. This home, since its construction, has been a family gathering place. The doors have always been open to guests, and we want to continue that tradition and welcome you!