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

Home in Chestertown

New place to stay

The Waterfront Retreat- *With Sauna and Hot Tub!*

Welcome To The Chesapeake Estate! Experience Waterfront luxury at this renovated retreat in Chestertown. Just 90 minutes from Baltimore and DC this home features an open layout, spacious living room with sweeping bay views. Enjoy the private guest house, heated pool, private beach and spacious deck for some of the most beautiful sunsets you've ever seen. Just minutes from historic downtown, experience comfort with coastal charm—perfect for relaxing, entertaining, or exploring the Eastern Shore.

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, 110 reviews

3 bedroom home with pool and game room

Forget your worries in this spacious and serene space. 5 miles outside of the town of Centreville. 15 miles to Chestertown. Custom built home sits on 4 acres in the middle of a 200 acre farm. First floor master bedroom and master bath. Living room, half bath, kitchen and dining area. Large back porch facing pool. Second story has full bathroom and two bedrooms. Each bedroom has an extra room inside. Also upstairs is a game room with a pool table. 1-king bed 1-full bed 1- queen bed 1- twin

Guest favorite

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

4.9 out of 5 average rating, 39 reviews

Chesapeake East Shore Chestertown,Pool (May1),Dock

A bright, airy, refurnished cottage set in the grounds of an 18th century farm on the eastern shore of Chesapeake Bay, shared pool (your private use 8am to 11am, 2pm to 5pm) & dock. Bring your watercraft & gear Layout is open kitchen, dining and living area. Master & bath on ground; upstairs 2 bedrm suite with bath Fiber optic & smartTVs Gas fireplace, central heat & AC Linens, kitchen utensils & Keurig coffee maker. GE washer and dryer. BBQ, deck chairs, picnic table, seating on water & dock

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

4.96 out of 5 average rating, 106 reviews

Beautiful Kent Island Getaway with Pool

PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a spacious bonus room for all your family entertaining. You will love the open floor plan with cathedral ceilings with a beautiful stone fireplace. The Master bedroom with jacuzzi tub. Surround sound music system. Desk with computer. Separate pool house with kitchen and bathroom great for entertaining. Outside features includes a Concrete saltwater pool (not heated) with huge fenced in backyard and KOI pond. Porches back and front.

Superhost

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, 6 reviews

Creek Cottage at Reed Creek | an ESVR property

Working Farm on Reeds Creek This lovely working farm is on a peninsula situated between Grove Creek and (surely not to your surprise) Reed Creek, which is just off of the Chester River. On this peninsula, historically called Wright's Neck, sits the Reeds Creek house, built by Colonel Thomas Wright in 1775. The Creek Cottage, a second home on the property, is a modern addition to the 170-acre farm offering privacy in the presence of a historical setting and powered by solar energy. Enjoy the

Guest favorite

Home in Worton

4.91 out of 5 average rating, 11 reviews

Cording Lodge*Pool*Pickleball/Basketball court

This beautiful property is the perfect place for your family vacation or to reconnect with friends. The outdoor living space is a dream! It has an in ground pool, beautiful patio with lots of seating area, bonfire pit and a BBQ grill, the perfect space to spend quality time together with family and friends! This 2 story, 5 bedroom house has all the amenities you need to make your weekend getaway or family vacation enjoyable. There’s boat launching at the coast guard only 1 mile from here!

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

4.93 out of 5 average rating, 161 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

A clear blue sky provides a backdrop for a view of calm water and distant trees along the shoreline. Various shades of green are presented in the foliage, enhancing the serene coastal environment. The image captures the tranquility of the area surrounding Betterton Beach.

Condo in Betterton

4.92 out of 5 average rating, 25 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.

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

4.9 out of 5 average rating, 42 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.

Superhost

An aerial view captures a secluded cottage nestled among lush trees, highlighting a heated saltwater pool illuminated softly. The outdoor area features a patio and deck, with warm lighting inviting relaxation in a tranquil setting.

Home in Queen Anne's County

4.73 out of 5 average rating, 15 reviews

River Heights Retreat (pool and hot tub)

Welcome to this secluded waterfront oasis with a heated salt water pool, hot tub and kayaks! Come and make memories with your family and friends! HIGHLIGHTS POOL HOT TUB BREEO FIREPIT ESPRESSO MACHINE This newly renovated cottage with a pool is located on the banks of a river and has lovely water views from the spacious kitchen and living room, and has a luxurious master suite with a king bed and a bathroom with a double vanity and a luxury tile shower.

Top guest favorite

An outdoor covered deck offers seating with a sectional sofa and a coffee table. High chairs are positioned at a bar-style table, with views of greenery and the bay in the distance. The area is brightened by natural light and features a welcoming atmosphere.

Condo in Betterton

5 out of 5 average rating, 33 reviews

Beach Haven Hideout

We are a small enclave of condos, perched high on a bluff, overlooking the Chesapeake Bay. From the deck you have wonderful views of the beach and the best Bay sunsets! We are no more than 100 steps to the beach, where you have a picnic pavilion, beach volleyball, and BBQ area with communal grills and picnic tables. This is the perfect getaway for small families or couples.

Guest favorite

The in-ground pool is surrounded by a spacious concrete deck, featuring several lounge chairs. A wooden fence provides privacy, with lush trees visible in the background. A patio area with a covered seating option can be seen to the right of the pool.

Home in Millington

4.88 out of 5 average rating, 73 reviews

The Peaceful Getaway (with private pool & hot tub)

Kick back and relax at this charming peaceful getaway, the perfect place to enjoy with friends and family! This beautiful 2 story spacious house is back off a dead end road, but still only minutes from the main highway. It’s very private with a beautiful in ground pool and hot tub behind the house! And also lots of space for outdoor cooking. Please no pets