Holiday rentals with breakfast in Queen Anne's County

Magnolia Cottage-BlueHeronLandng

QUEEN bed, two TWIN beds, QUEEN sofa bed Sanctuary nestled right at the water's edge. This charming guest house boasts a loft with a Queen bed and two twin beds, and a queen sleeper sofa on the main level, ensuring a restful night's sleep for everyone. There is a fully equipped kitchen and an open concept living area with plenty of seating. A full bathroom, complete with a stacked washer/dryer, adds convenience to your retreat. Embrace the island tranquility as your cares wash away.

Waterfront 3bed/2.5 bath w/dock&beach close 2 town

"Chester River Dreams" is a waterfront property located less than 5 mi to the center of town. There is a dock and “L” head to sit and relax, and a small beach area. A nice deck, fire pit, & kayaks and paddle boards to use. The property has high speed internet and smart TVs in the living room and family room & all bedrooms. New for 2025, the upstairs was renovated to include a queen , 2 twins, walk in closet, and full bath. We also added an office area to front bedroom.

Camellia -BlueHeronLandingB&B

KING SUITE w sitting room and waterfront patio Located on the first floor, this King suite features high ceilings and traditional wood shutters welcoming the morning sun. The private bath with a sleek walk-in shower promises a refreshing start to your day. Room amenities include a king bed, a commanding walnut armoire and a waterfront sitting room with wood burning fireplace. Wrap yourself in the luxury and tranquility. (525 sq ft)

Private 2 bedroom suite

Perfect for families or wedding party guests who want to share a suite with 2 Queen bedrooms, a full bath with mini kitchen area & amenities. This is 1 of 3 listings for this house space. Book this to get the suite with both bedrooms and 1 bath. There is an additional twin bed I can set up in the larger room if you need to add a 3rd person for that room, so potentially room for 5 people for the suite.

Hydrangea -BlueHeronLandingB&B

QUEEN BEDROOM w waterfront balcony Welcome to the serenity of the Blue Hydrangea Room, a second-floor retreat embracing comfort and charm. This Queen room offers a private full bathroom, walk-in closet, mini-fridge, TV, iron, and a dedicated workspace. Unwind out on the waterfront balcony taking in the picturesque view. This is a delightful way to relax and reset. (350 sq ft)

Guest Suite in a Victorian on the Chester River

Our lovingly-restored Millington Manor is the original home of the local doctor, built in 1868. Our small town has a liquor store and grocery. We are a 15-minute ride to Chestertown, home of Washington College and host to wonderful restaurants, lovely shops, galleries and a theatre. Crumpton's auction is minutes away.

Crew Quarters

Crew Quarters at the Inn at Haven Harbour. Six distinct sleeping areas (three queen-size beds, twin bunk beds, a twin-size daybed with trundle and two pull-out sofas). Two full baths, full kitchen (stocked), dining room and laundry. Large second floor deck overlooking spacious waterfront lawn.

Rustic & Pretty Private Bed & Bath

Quiet house setting on Kent Island. Private, spacious bedroom suite (queen size bed) & bath with rustic pine interior throughout the house. Bright room with dressing table. Mini kitchen area with amenities. Close to Bay Bridge & local wedding venues.

Rustic & Elegant Private Bed & Bath

Quiet house setting on Kent Island. Private, spacious bedroom suite (queen size bed) & bath with rustic pine interior throughout the house. Mini kitchen area with amenities. Close to Bay Bridge and local wedding venues.