Vacation rentals in Kent Island Narrows

Halcyon house. Lovely views on MD eastern shore.

This charming apartment is located on the Chester river on Maryland's Eastern Shore. The wildlife is abundant and generally very active. The sun rise and sunsets can be spectacular. The property is 20 minutes from Annapolis and 50 minutes from DC. The newly renovated apartment has all new appliances and a well stocked kitchen with many herbs and spices, condiments, coffee, tea, cream and sugar etc. The 8 mile long Cross Island Trail starts a block from the house and leads to several restaurant

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.

River Front house / dock/hot tub

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.

Cass-Away A Luxury Houseboat

Kent Narrows Rentals welcomes you aboard Cass-Away! A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a living room, kitchen, 2 bedrooms, 2 full baths, and a magnificent view from the rooftop deck! With 9 waterfront bars/restaurants within walking distance, you can get a taste of what the eastern shore has to offer. Minutes from the Bay Bridge and a short drive to Annapolis, D.C., St. Michael’s, and Ocean City. NO Fishing/Crabbing on property! Check our website for more info!

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5-star retreat for those who value tranquility over spectacle. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our reviews.

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Inspiration Guest Suite - Cinnamon By The Bay

Inspiration is a cozy, bright studio with a full-size bed, seating area, kitchenette, and workspace. It is located upstairs in the Cinnamon By The Bay Inn. Main Street shopping, Java Rock coffee shop, and The Mainstay music venue are right outside the front entrance. Ferry Beach, Eastern Neck Wildlife Refuge, museums, charter fishing, kayaking, and marinas are a short walk or drive. Enjoy stunning sunsets and lively conversations on the community deck. Suite is limited to 2 guests.

Cozy Retreat w/Private Beach Access

Welcome to our charming Annapolis retreat! Nestled in a quiet community on the Chesapeake bay, Barefoot Cottage offers a perfect blend of comfort and convenience. Enjoy a stroll around iconic landmarks, savor local cuisine, or unwind with a walk on the beach. Thoughtfully interiors and modern amenities, our Airbnb promises a memorable stay for your solo trip, romantic getaway, sailing enthusiasts or USNA visitor. Book now for an unforgettable experience in this historic maritime city!

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.

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

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.