Holiday rentals in Wye River Farms

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.

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

Traveler Guest Suite - Cinnamon By The Bay

The Traveler offers a private bedroom and fully equipped eat-in kitchen. For those guests who prefer separation from their dining area, but don’t need a separate living space, Traveler is a perfect match. Enjoy the comfort of not being awaken when someone sneaks a midnight snack, all while being easy walking distance to Rock Hall's shopping, coffee shop, restaurants, music venue, and festivities. It is one of our pet-friendly suites with easy access to the community back deck and rear yard.

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.

Cass-N-Reel Luxury Houseboat

Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With 1 bedroom, 1 bathroom, and a gorgeous covered rear facing deck; this is the ultimate couples retreat! 9 waterfront/waterview bars/restaurants within walking distance! Get a taste of what the eastern shore has to offer. Minutes from the Chesapeake Bay Bridge and a short drive to Annapolis, D.C., St. Michaels, and Ocean City. Come stay and live like a local! NO Fishing/Crabbing on property

Adorable Lake Front 1BR Cottage-fully furnished!

This charming 1BR/ 1Bath cottage is located next to my primary residence. The cottage has its own private deck overlooking the Wye Mills Community Lake. The yard is spacious and pets are welcome. The yard is not closed in but safe for dogs who do not roam far. There is 1 queen size bed and queen pull out couch in the living room. Kitchen is equipped with basic appliances/ cooking and serving utensils and a full size washer and dryer. The bathroom has a stand up shower and basic necessities.

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.

Bay Breeze - 3BR Waterfront Chester River Retreat

Remodeled in 2023, this light-filled, 2-story private home offers 2,100 sqft of stylish comfort—perfect for a relaxing getaway. Take in breathtaking sunsets from the double-decker porches overlooking the Chester River, unwind by the fire pit, host a crab feast or enjoy a BBQ on the private dock. Ideally located just 5-10 minutes from Kent Island’s top restaurants and wedding venues, with a community playground, pavilion, and boat ramp just steps away. Your waterfont escape awaits!

Private basement and entrance

Relax in this peaceful SUITE. The renovated basement SUITE has a private entrance and long-term stay facilities, including a free in-unit washer and dryer, refrigerator, and stove. Convenience stores are just a minute's walk away in a walkable neighborhood We are proud to provide 5-star services for our guests, ensuring they have the best time during their stay with us. Please note that: ==> ***We do not accommodate reservations for someone else*** <==

Cozy Historic Cabin on the Water

This property is a nature lovers paradise! Step into our almost 300-year-old, historic cabin with exposed beams, wooden walls, and modern fireplaces. This cabin, dating back to 1787, is nestled alongside the Wye River. The views from the dock provide a tranquil setting to unwind and escape the pressures of everyday life. Wake up to the melodies of nature and enjoy observing the wildlife in their natural habitat. WiFi is not available.

Eastern Shore Charm on Winchester Creek

My place is close to restaurants and dining and great views. You’ll love my place because of the comfy bed, the coziness, and the views. My place is good for couples, solo adventurers, and business travelers; sorry no kids. Need at least three days notice to book guest house, I like to be here when you arrive, thus schedule my social activities around bookings.

Cozy Waterfront Apartment Chester, MD

Hello travelers!! Looking for a cozy & comfortable place to stay on Kent Island? Come enjoy our clean & beautifully renovated apartment above our family home, overlooking Cox Creek. This apt. Is built above our garage. Private entrance on the side of our house (20 steep steps up). 1 bedroom, queen bed. WiFi included. Private porch to enjoy water view!