Vacation rentals with a pool in Kent County

Find and book unique homes with a pool on Airbnb

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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Guest favorite

Cottage in Chestertown

4.91 out of 5 average rating, 34 reviews

Chesapeake East Shore Chestertown, Pool & 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 6 hours a day) & 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, fire pit

Guest favorite

Farm stay in Centreville

4.93 out of 5 average rating, 76 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

Home in Stevensville

4.98 out of 5 average rating, 84 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.

Guest favorite

Home in Church Hill

4.89 out of 5 average rating, 53 reviews

Private Peaceful Waterfront House w/ Pool, Hot Tub

Family owned beautiful waterfront home with a fully stocked kitchen, dining room, master bedroom and large living areas. 5 acres to explore with a beautiful river view. The house is located back in off of a gravel drive. There are a few neighbors around the property but you will rarely, if ever see them. Some of the things this property has to offer. -Salt water pool (Pool will be closing end of September to April for the winter) -Outdoor Table & Chairs -Grill -Kayaks -Fire Pit -Hot Tub

Guest favorite

Casa particular in Chestertown

4.94 out of 5 average rating, 129 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

Home in Centreville

5 out of 5 average rating, 21 reviews

Middle Fox Cove (New Hot Tub!)

With incredible views of the Corsica River from almost every room and set on 6 acres amidst idyllic farms, your home away from home calls. A 5-bedroom, 6.5-bath waterfront oasis, Middle Fox Cove is the key to unlocking a memorable getaway you will never want to leave behind. This 5000 square foot home is a tranquil masterpiece that makes room for relaxing and recreating. Bring the entire family or just a quiet retreat for two - make this the memorable experience you’ve been looking for.

Superhost

Home in Rock Hall

4.84 out of 5 average rating, 19 reviews

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

This waterfront 4 BR, 2 1/2 BA Private house in the town of Rock Hall was renovated for 2021 season and now for 2023, a NEW Hot Tub. It has a 300' pier with 4' MWD in Swan Creek, a private pool and the best sunsets to enjoy while enjoying the deck or having coctails while relaxing under the shade trees. Kayaks, bikes and more are provided for your entertainment. Walk or bike to town and enjoy restaraunts and shops. A great property for a family vacation off the Chesapeake Bay

Guest favorite

Bungalow in Rock Hall

4.89 out of 5 average rating, 37 reviews

Welcome to Mermaid Haven!

This 3 bedroom, 2 bath home located in the town of Rock Hall, MD is within walking distance to downtown Main street. The beach and several public boat ramps are just a short distance from the much sought after Haven Road location. Water view at the end of the road. Plenty of parking, oversized garage, deck, and BBQ grill. Local attractions include: Ferry beach, sailing, power boating, kayaking, paddle boarding, fishing, crabbing, biking, hiking and Eastern Neck Wildlife Preserve.

Guest favorite

Villa in Centreville

5 out of 5 average rating, 45 reviews

Blake House Historic Estate with Private Inn

**HEATABLE POOL FROM 4/19** Blake House represents one of the oldest colonial homes in Maryland, built by British settler, Charles Blake, of London, England, in 1691. The house is nestled within 12 acres of manicured gardens, boasting an abundance of indigenous and foreign flora, and surrounded by direct water access. But the most unique feature of this property is the Crown and Anchor Inn (circa. 1735), originally located in Southern Baltimore and moved to the estate in 1941.

Superhost

Condo in Betterton

4.92 out of 5 average rating, 36 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.

Guest favorite

Barn in Chestertown

5 out of 5 average rating, 20 reviews

"The Barn" unique design, farm views, beach access

This century-old barn was lovingly converted into a home with unique architectural features. Highlights include a rooftop glass cupola for 365 degree views of your surroundings, an elevated screened dining porch nestled among oak trees, spiral staircase, and interior featuring salvaged materials from local historic farms. Surrounded by protected farmland and woods, it lies along a quiet and private road but

Superhost

Home in Worton

5 out of 5 average rating, 3 reviews

Holly Point on the Water

This is a special place. Holly Point was meticulously designed to be a grand oasis on the water. Privacy and solitude await at the end of the mile long driveway. This 12,000 square foot home offers a huge master suite on the first floor. The other 4 bedrooms are upstairs and there is an elevator if needed. The kitchen has 2 islands, 2 sinks, 2 dishwashers...it's large and any home cook will love it.