Holiday 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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Guest favourite

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 favourite

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 favourite

Home in Stevensville

4.96 out of 5 average rating, 107 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

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

Top guest favourite

Casa particular in Chestertown

4.93 out of 5 average rating, 162 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!

Superhost

Apartment 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.

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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.

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Home in Chestertown

New place to stay

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

Welcome To Paradise! Experience Waterfront luxury at this renovated retreat in a very quiet Chestertown neighborhood. The home features an open layout, spacious living room with sweeping bay views. Enjoy the private guest house, heated pool, 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.

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.

Top guest favourite

Apartment 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 favourite

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

Top guest favourite

Home in Rock Hall

5 out of 5 average rating, 15 reviews

The Mariner's House

Enjoy this recently renovated three bedroom and two bath home in the charming town of Rock Hall, Maryland. Just half a mile from Main Street shops and delicious waterfront restaurants! This home is affiliated with Rock Hall Landing Marina which allows all of our guest to use our great amenities. We look forward to having you stay with us!