Vacation rentals with a pool in Kent County

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Top-rated rentals with a pool in Kent County

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

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Superhost

A tranquil saltwater pool is surrounded by lush green grass, featuring a clear blue surface reflecting the sky. Lawn chairs are positioned nearby, with a wooden fence and trees in the background, alongside a house and an American flag gently waving.

Cottage in Chestertown

4.91 out of 5 average rating, 35 reviews

Chesapeake East Shore Chestertown,Pool (May1),Dock

AntoinetteRating, 5 stars8 months ago

We loved our stay at the cottage. Everything was clean and well maintained inside and out. We especially loved the gorgeous surroundings. The property was beautiful and peaceful. We enjoyed daily swims in the pool and time at the dock. Robert was a wonderful host and made everything very clear and easy as well as was easy to communicate with. We couldn't have asked for a better get away. Chestertown is adorable and fun to check out. We hope to return in the future.

Guest favorite

A private pool features a clear blue surface, surrounded by a concrete patio. Lush greenery borders the area, while a wooden railing encloses the space. In the background, a barn and a greenhouse complement the serene farm setting.

Farm stay in Centreville

4.93 out of 5 average rating, 89 reviews

3 bedroom home with pool and game room

TerriRating, 5 stars3 days ago

We were in town for a couple of days with family and this home worked out great for us. The large living room, dining room, and kitchen area was perfect for us to all be together during our stay. We enjoyed the back porch looking over the pool area and watching the deer roam the property. There is also a large tree swing that we enjoyed and we got some great photos. Three of the beds all have soft plush mattresses. Too soft for me, but that is just an individual preference. Kerri was very responsive, helpful, and friendly. We would definitely stay again!

Guest favorite

A covered porch features white railings and ceiling fans, offering a view of the spacious saltwater pool surrounded by lush greenery. The outdoor area includes well-maintained landscaping and a barbeque grill, providing an inviting space for relaxation and gatherings.

Home in Stevensville

4.95 out of 5 average rating, 87 reviews

Beautiful Kent Island Getaway with Pool

LaurenRating, 5 stars5 months ago

The house was perfect for staying in the area for a friend’s wedding! The house was comfy and well stocked with everything we needed. Virginia was super responsive and so helpful- we lost our car keys the morning we were supposed to leave and she was very accommodating! Would definitely come back- curious about the pool in the summer 😎 Was within running distance from a trail and a beautiful nature preserve.

Guest favorite

A two-story home is seen from the perspective of a patio area, featuring a large saltwater pool in the foreground. Lounge chairs are arranged around the pool, and string lights are hung overhead. A garden area with plants borders the pool, adding greenery to the scene.

Home in Church Hill

4.89 out of 5 average rating, 53 reviews

Private Peaceful Waterfront House w/ Pool, Hot Tub

LenaRating, 5 stars9 months ago

This was our 2nd year at Peaceful Waters. It is indeed just that! Peaceful! Perfect and beautiful location. Everything needed is there to assure a wonderful carefree stay. The place is well stocked, clean and is just as it reads and appears! My group of 16 loved the place AGAIN this year. Hopefully, planning to go back next year. Matthew and Rose are great to work with! ❤️

Top guest favorite

An inground pool is surrounded by brick paving, with several lounge chairs positioned nearby. The pool's turquoise water is partially shaded by a large tree, providing a serene outdoor setting. Lush green grass and a wrought-iron fence are visible in the background.

Casa particular in Chestertown

4.92 out of 5 average rating, 143 reviews

Red, White & Waterview Studio Apt with pool

RobRating, 5 stars1 month ago

We were in Chestertown for one night to drop our daughter at Washington College. The studio apartment was a perfect place to recharge before making our trip home. Host was a proactive communicator which made finding and checking into her place simple. Bed was comfy and space clean and relaxed. Appreciated the hospitality of our host.

Superhost

Home in Rock Hall

4.86 out of 5 average rating, 21 reviews

Waterfront w/pier, Hot Tub, pool, and in town

ToniRating, 5 stars4 months ago

My family and I celebrated Christmas here so we could all be together… The location was perfect on the water and very close to where my parents live. The living room and dining room were actually bigger than the pictures showed. There were eight of us and a dog plenty of room.

Superhost

A fenced swimming pool is visible under clear blue sky, with sunlight reflecting off the water's surface. Several white lounge chairs surround the pool, complemented by a shaded table and umbrella nearby. The area appears well-maintained and inviting for relaxation.

Condo in Betterton

4.92 out of 5 average rating, 36 reviews

3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

CaitlinRating, 5 stars7 months ago

A great sunset view from the balcony, such a nice quiet river/bay beach, peaceful community to walk around. Would stay in again! Would note there’s 1 flight of stairs up as it’s a 2nd floor condo of sorts; and a big hill/stairs down to the beach. However, also a parking lot if needed to drive to the beach. Beach chairs were nice to have. There was no cooking oil but I think we left some :) I would only ask they replace the dining room chair with the hole in the seat. The pool was closed and that was not expected! Adam was very responsive when we messaged.

Top guest favorite

A clear swimming pool reflects the overcast sky and surrounding buildings. Multiple white lounge chairs are arranged around the pool, accompanied by blue umbrellas offering shade. The pool area is enclosed by a low fence, creating a serene atmosphere for relaxation.

Home in Rock Hall

5 out of 5 average rating, 13 reviews

The Mariner's House

VivianRating, 5 stars1 month ago

We thoroughly enjoyed our stay. The location was perfect. The Bay was across the street. There were many extra Amenities available to us on the grounds. The house was in a perfect location, very well maintained, fully equipped, very cozy, and within walking distance to everything. The neighborhood was quiet and peaceful. Megan was the perfect host. She was very welcoming, friendly, warm, and responsive. Everything went smoothly and was exactly how she said that it would be. There were no unexpected surprises. We can't wait to go back!

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Popular amenities for Kent County rentals with a pool

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House rentals with a pool

The exterior of a two-story farmhouse is visible, featuring a spacious patio with lounge chairs and bright red umbrellas. A clear swimming pool reflects the blue sky, providing a serene space for relaxation. Lush greenery surrounds the property.

Home in Centreville

5 out of 5 average rating, 5 reviews

Creek Cottage at Reed Creek | an ESVR property

PatrieceRating, 5 stars44 months ago

The Creek Cottage at RCF is nothing less than amazing. This is the perfect getaway for privacy, peace and nature. We saw deer, foxes, fish, birds and tons of butterflies. The scenery is so beautiful and serene. The house was just enough space for the 5 of us and our dog - who loved sitting on the enclosed porch to watch us at the pool. The pool was perfect, the river was beautiful and it was nice to just sit and watch the scenery. Bryan, the property manager, was also great and suggested we try out the Crab Shack in Easton - these were the best crabs at a price we couldn’t believe (we got a bushel)! The first floor is fully accessible for those with special needs, but note that the bed sits high so a step stool may be needed. Also, beware of the horse flies - they can be pretty aggressive and intimidating, but we found ways to manage. We certainly loved our family staycation at the Creek Cottage and would love to come back in the future!

Home in Chestertown

4.67 out of 5 average rating, 3 reviews

Pet-Friendly Home on Chester River w/ Dock!

JosephRating, 5 stars2 weeks ago

Been coming to Chestertown for the last 7 years and this one of the best spots. Perfect location on the river with awesome views from the sun room. Will certainly be back!

Guest favorite

A serene in-ground swimming pool is surrounded by lush green grass and trees. The reflection of nearby trees is visible on the water's surface. A charming blue house stands in the background, with access to the waterfront just beyond the pool.

Home in Worton

4.97 out of 5 average rating, 30 reviews

Chesapeake Bay Estate; 2 Houses, Beach&Heated Pool

LauraRating, 5 stars8 months ago

My family loved staying here. We had my 3-month old and my sister brought her 8-month old so we were looking for a place that could keep everyone entertained in one location and this place did just that! We enjoyed bird watching, collecting rocks on the beach, swimming in the heated pool, and watching the sunset from the hot tub in the evenings. This was also the first time I could say that the listing looked better in person than the pictures. Thank you Joni for letting us stay here! We made some amazing memories!

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Vacation rentals with a pool in Kent County

Top-rated rentals with a pool in Kent County

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