
Herons Roost
This 2,230-square-foot dwelling accommodates up to 11 guests, offering complimentary Wi-Fi, an on-site kitchen, and free private parking, with a 10:00 AM check-out time.

The Weekender | An Esvr Property
The 2-bathroom rental features a bright, open-concept layout, sleeps four guests comfortably, and includes a fully equipped kitchen with a fridge, microwave, and dishwasher, plus a garden, patio, and parking.

The Cottage At Broad Creek
The one-bedroom, one-bathroom house includes a gourmet kitchen, private dock for kayaking, sunroom, fireplace, and accommodates two guests, perfect for a relaxing getaway.

Kent Island Waterfront | Pool | Outdoor Dining | Stunning View | Private Dock
This 3,520-square-foot vacation rental boasts five bedrooms, three bathrooms, sleeps ten guests, and includes a private pool, spa, tennis court, and on-site amenities such as an arcade/game room and barbecue grills.

Book Now For 15% Off. Waterfront, Dock, Hot Tub, Sandy Beach, Elevator!

Minutes From Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock
The spacious 1710 square foot house comfortably accommodates up to eight guests in its four bedrooms. Enjoy modern conveniences like a fully equipped kitchen, air conditioning, a cozy fireplace, and a private terrace or balcony, plus outdoor amenities like a garden and barbecue grills.

House On The Bay With Private Beach Access & Panoramic Bridge Views
This three-bedroom, two-bathroom vacation rental sleeps six, boasts a fully equipped kitchen, private patio, free WiFi, and a spa, offering easy access to Love Point State Park and Island Dog Park (within 12 miles).

Minutes From Downtown St. Michaels | Pool | Pickle Ball Court | Private Dock | K

Cottage #6 Oar & Anchor Cottage
The cozy cabin has one bedroom and one bathroom, accommodating up to four guests. It offers a fully equipped kitchen, a dining table, a queen-size bed, and a futon that converts into a bed, as well as outdoor amenities like a fire pit, corn hole, and horseshoes.

Grandview - Cottage 1a, King Bed, Pool, Bay, Wifi
The cottage features one bedroom and one bathroom, accommodating up to two guests. Enjoy amenities like a full kitchen, screened porch, fireplace, WiFi, air conditioning, grill, two piers, and access to a swimming pool.

Downtown St. Michaels | Porch + Pet-friendly
This pet-friendly accommodation features a queen bed, a kitchenette, fast WiFi, and private parking, accommodating up to two guests.

Jewel Of The Tred Avon
This 6,800 square foot, 5-bedroom rental sleeps 19 guests and features air conditioning, a private swimming pool, a garden, a fitness center, and complimentary high-speed WiFi.





















