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Private | Near BayBridge | Wedding Venue Proximity

Welcome to your Kent Island getaway! This thoughtfully decorated, private guesthouse is minutes from the Bay Bridge, offering the perfect retreat for families, couples, or friends. Skip the hotel and relax in a fully stocked home with plenty of space, a large backyard for activities, and cozy touches throughout. Whether you're here for a wedding, visiting the Naval Academy or DC, or simply exploring the Eastern Shore, you'll love the comfort, convenience, and local charm this home has to offer.

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.

Heron Roost

Heron Roost is a centrally-located waterfront apartment on a private gated lot with a heated pool. The view from your sun deck is the best on the property with spectacular sunrise and moonrise. We are conveniently located about one mile from the Chesapeake Bay Beach Club and twenty minutes from the US Naval Academy in Annapolis. There are numerous excellent restaurants and bars nearby and the towns of Easton and St Michael’s are close. Please come and enjoy our peaceful and unique property.

Chesapeake Cottage

VERY CLOSE to island wedding venues. Cottage is a private detached 1st floor dwelling and has off street parking. Queen bed & trundle with 2 single beds, sleeps 4. There's a full/stocked kitchen & bath, large TV, small dining table, Keurig & coffee pods. Wifi and streaming service's included. Easy access with keyless entry. Efficiency space. Smoke/Vape allowed on front porch only. Located near the Bay bridge and bike paths, Historic downtown, winery & restaurants. *Message with any questions.

River Front, Private Single Family Home

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away

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.

Waterfront Farmhouse Meets Modern Luxury

Enjoy all that the Eastern Shore has to offer while staying at the neoclassical 19th-century "Osprey's Reach" farmhouse. Osprey's Reach blends the original character of Kent Island with modern comforts of a full house restoration, all while enjoying stunning sunsets over the Chesapeake, from the private dock or poolside. Kent Island is centrally located for short day trips to Annapolis, Easton, St. Michael's or Chestertown, with family-friendly dining and shopping options on-island.

Kent Island Waterfront Home

Enjoy a delightful stay at our waterfront 2 bedroom house for your Kent Island trip. The unit is equipped with a full kitchen including cookware and essentials for all your cooking needs, microwave, Wifi, TV, security cameras. Blankets, pillows, linens and bath towels. The house is a Self-Check-in, perfectly situated near all the local Kent Island Restaurants, Shops, Wedding Venues, Public beach access, wineries and so many more attractions to enjoy. We look forward to hosting you!

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.