Holiday rentals in Wye River Farms

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

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.

Cheerful & Spacious Shore Life Beauty!

Welcome to our charming yet peaceful abode & island oasis where sailing, marine life, & bay exploration exceed the standard! This exceptional home is conveniently located to a variety of high quality restaurants, parks, outdoor activities, spas, beaches, wedding venues, & other entertainment including live music, hunting, & antiquing while also being 20-minutes from Annapolis & 1-hour from Baltimore City & DC. Let this be your definitive choice for a magical destination you'll forever remember.

Screened Porch | Near Bay Bridge & USNA | Big Yard

Welcome to your perfect Kent Island getaway! This newly listed home features a tastefully decorated 3-bedroom home, accommodating up to 8 guests. Enjoy the screened-in porch, wrap-around deck with rocking chairs, and large backyard with outdoor dining for any fun activity. You will be minutes from the Bay Bridge and several of Kent Island's premier venues and restaurants, making this home ideal for wedding guests, an Annapolis/DC trip, or if you're simply looking to explore the Eastern Shore.

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.

*NewHotTub*LuxuryCoastal*CloseToWeddingVenues

Come enjoy the coastal lifestyle of the Chesapeake Bay with friends & family! Relax every evening on the back deck watching the beautiful cattails & sun set into the Bay every night. This spacious home can sleep 10 guests and is furnished with all new high-end furnishings, linens, 100% cotton sheets, luxury towels, & a fully stocked kitchen! We are very close to all the wedding venues on Kent Island plus 1 mile of all the restaurants,marinas,& live music. No additional visitors/guests allowed.

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.

Comfortable Single Floor Living

Make some memories at this unique and family-friendly place. Comfortable one floor living with space to spread out, hang out, and enjoy! Split design with master on one end opposite other sleeping . Inside bar area and covered deck to kick back and relax. Fenced area for your four-legged friends, and a sport court out back for a casual game of basketball or pickleball. Everything you should need inside to feel at home. Sights and sounds give you that country feel without being too remote.

Wye Topia | an ESVR property

Ideal felicity and perfection! This 3,600 square foot, 4-bedroom, 3.5-bathroom Wye River waterfront was designed with your comfort in mind, the open floor plan features a modern interior and incorporates a flow-through living, entertaining and dining area and a generous foodie inspired kitchen. Drift off to sleep each night in the opulent main suite that comes complete with an ensuite bathroom, direct access to an expansive deck, and water views. The wonderfully secluded property boasts a

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 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!

Optional Heated Pool + Hot tub + Fire Pit+ Fenced

Escape to this luxurious country retreat in Centreville MD, where modern elegance meets tranquil outdoor living. This professionally designed home offers an exceptional blend of comfort & style, perfect for those seeking relaxation & entertainment. The outdoor area is an entertainer's dream, featuring an inground pool, a 12-person fire pit, an 8-person hot tub, & an outdoor kitchen. This luxurious country haven provides all the amenities needed for an unforgettable stay!