Holiday rentals with a pool in Kent County

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

Location · Family · Nearby

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

Location · Family · Nearby

River Heights Retreat (hot tub and luxury)

Welcome to this secluded waterfront oasis with a Heated SALT WATER POOL, CABANA, HOT TUB, BEAUTIFUL master suite, and kayaks! Come and make memories with your family and friends or enjoy a ROMANTIC getaway WITH YOUR SPOUSE, 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 and has a luxurious master suite with a king bed and a bathroom with a double vanity and a luxury tile shower.

Family · Value · Sleep quality

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.

Value · Family · Quiet

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!

Family · Location · Decor

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.

Location · Family · Indoor spaces

Pet-Friendly Home on Chester River w/ Dock!

Ideal for Goose & Deer Hunting Trips | Kayaks Provided | Crab Traps Calling all outdoor explorers! Lower your anchor at this 4-bedroom, 4.5-bath vacation rental in Chestertown. With an enclosed porch, a boat dock right on the Chester River, and a basement game room, this spacious abode promises endless family fun! When you're ready to explore, head 1 mile to the Historic District for sightseeing, souvenir shopping, local seasonal events, and of course, the Chestertown Farmer's Market.

Family · Location · Checkout

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.

Value · Family · Layout

Waterfront Wellness - *With Pool and Hot Tub!*

Welcome To Paradise! 🌊 Private Beach | 🏊 Heated Pool | 🔥 Sauna | 💦 Hot Tub| 🌅 Sunset Views This Chesapeake Bay retreat features a private beach, heated pool, sauna, hot tub, and guest house in a peaceful waterfront neighborhood. Enjoy coffee on the deck, afternoons swimming or kayaking, and evenings watching sailboats pass as the sun sets over the bay. Just minutes from historic downtown Chestertown, shops, restaurants, and marinas for the perfect Eastern Shore getaway.

Value · Location · Condition

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, 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!

Location · Value · Amenities

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.

Value · Location · Comfort

Blake House Historic Estate with Private Inn

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.

Location · Value · Bathroom