Vacation 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

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

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.

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

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!

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.

River Heights Retreat (hot tub and luxury)

Welcome to this secluded waterfront oasis with a romantic master suite, a hot tub and kayaks! Come and make memories with your family and friends or enjoy a ROMANTIC getaway, 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.

Coastal Escape, in The Heart of Rock Hall!

New Coastal Retreat in the Heart of Rock Hall! This newly built 3BR, 2.5BA home featuring modern coastal décor and an unbeatable location! Enjoy coffee on the front porch, then gather in the private backyard with a grill, picnic table, and fire pit. Walk to Rock Hall’s marinas, shops, and restaurants, or spend the day boating, fishing, kayaking, and exploring the Chesapeake Bay. End your evening with breathtaking sunsets and small-town charm...Your perfect Rock Hall getaway awaits!

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.

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

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.

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!