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Waterfront Paradise w/ Pier - kayak to Chestertown

Escape to our private paradise where you can enjoy breathtaking sunsets from our pier, catch your own fish/crabs, sit around the fire pit by our 200+ foot private beach while gazing at countless stars, try our outdoor sauna w/panoramic view. It's a destination you can enjoy all year. Our home is located a short bike ride to Historic Chestertown, or you can take one of our kayaks in while you enjoy the Chester River. Bedroom 1: king bed+daybed w/trundle Bedroom 2: Queen Bedroom 3: Queen & bunkbed

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Frosty Acres Choptank River Farm

Bring your family for a memorable stay on our family waterfront farm, "Frosty Acres." Located on Maryland's Eastern Shore outside of Greensboro and Ridgely the 3 bed/2 bath Victorian house sits on 60 waterfront acres surrounded by barns, fields, woods & farmland, once occupied by Choptank River Native Indians! Walk the trails and dirt roads that will take you through the farm to the campground area where you can launch your own boat up to 25 ft, BBQ, kayak, fish, swim and tent camp by the fire.

Waterfront Getaway w/ Pool + Beaches+ Hot Tub +BBQ

Unwind at this serene and secluded getaway—perfect for couples, small groups, families or anyone looking to relax by the water. This charming one-bedroom guest house offers comfort and style with a plush king-size bed, a fully equipped kitchen with a gas stove, and a spacious living area with a queen-size pullout sofa. Step outside to your private, oversized balcony overlooking the river—an ideal spot for morning coffee, al fresco dining, or winding down with sunset views and a glass of wine.

The Fitz Inn

Arrive by boat or car to our cozy 1 BD/1BA private 500 sq ft cottage! Enjoy wineries, restaurants, bars & waterfront activities & return to the peaceful Fitz Inn. Sip coffee at sunrise & wine at sunset on Cox Creek (Benton's Pleasure area). Ideal for 2 guests, but can accommodate 4. Listing has AIRBNB exemption from hosting animals, including service & emotional support ones (please see property description for more details). No smoking. Flexible reschedule option with $100 administrative fee.

Crab Alley | Waterfront Home + Hot Tub + Game Room

BNB Breeze Presents: Crab Alley Welcome to Crab Alley, a stunning Bayfront home nestled in the serene surroundings of Chester, Maryland. This beautiful property offers a perfect blend of relaxation and adventure, making it an ideal getaway for families or groups of friends. With its prime waterfront location, guests can enjoy breathtaking views and easy access to water activities right from the comfort of their home. - HOT TUB! - Boat Dock - Deck w/ Bay Views - Game Room - Outdoor Dining table

Loon Cottage on Leeds Creek

Loon Cottage is a place where you can get away, put your phones down, take long walks in the woods, read on the patio, canoe on the river, cook big meals, and spend time with your favorite people. It’s cozy, comfortable, and just a little bit nostalgic. Decamp from the City to work remotely for a few days. Bring the family out to change the scenery on your weekend routine. Pack friends into the car for some low key shenanigans. Or some combination of all the above. Follow along @loon_cottage

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Relax in this Stylish Coastal-Country Home w/Sauna & 3 acres of outdoor living! Perfect for Families & Wedding Groups! We're conveniently located to many areas/cities: Annapolis- 15 miles Baltimore- 40 Wash. DC- 45 Easton- 30 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions, including Chesapeake Beaches. This is a Non-Smoking House. Also No Pets or Parties & 14 max guests (8 max adults). Book Today!

Waterfront | Swim Spa + Sauna + Beach + Game Room

Escape to Oyster Bay Getaway, a stunning 4-bedroom waterfront retreat designed for relaxation and fun. Enjoy serene water views throughout the home, unwind in the swim spa or sauna, and cozy up by the indoor fireplace. Step outside to a private dock and fire pit perfect for evenings under the stars. The garage game room (unconditioned) and indoor lounge with poker table make this the ideal getaway for families and groups seeking comfort, entertainment, and a true waterfront experience.

Anchors Away

Anchors Away beckons as your tranquil waterfront escape! Inside, the cozy gas fireplace awaits. Savor a coffee bar experience and utilize the well-appointed kitchen. Unwind in the screened-in porch with a book and river views. Outdoors, the dock invites relaxation by the water. Gather around the wood fire pit for memorable nights under the stars. Enjoy Kayaks, fishing poles and family games! Anchors Away promises an unforgettable riverside retreat. We look forward to hosting you!

Waterfront Modern Guest Barn

Find peace and reconnect with nature at this award winning guest barn. With its simple geometry and bucolic setting overlooking a quiet river of the Eastern Shore, this gem at the edge of a farm field could easily be mistaken for a working barn. But when you slide open the pair of two-story barn doors, you find a beautiful modern guesthouse full of light from the wall of windows facing the river. The setting is incredibly peaceful, and is a wonderful romantic escape or family getaway.

Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit

Kick back and relax in this calm, charming newly renovated coastal farmhouse waterfront two-story home with private pier/dock! Gorgeous sunrises! Experience fresh Maryland Crabs & fish caught from your private pier & enjoy the peace, serenity, bay breezes & waterfront green space! Connect to nature and explore Meredith Creek on the Chesapeake Bay by kayak or boat! Super CLEAN & new with water views from dining, living room, kitchen and bedroom! 1.5 miles to the Beach!