Holiday rentals with breakfast in Queen Anne's County

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Top-rated Holiday Accommodation with Breakfast in Queen Anne's County

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Apartment in Greensboro

4.93 out of 5 average rating, 110 reviews

Awesome River House Waterfront Apartment

Having been called "a treehouse on the river" by many guests since there is a oneness with nature afforded by the design of our home. The ever-changing view of the river is always enchanting as is the ebb & flow of the tide on the Choptank River. Our dock provides excellent river access and is only 20 feet from the house and has a new (2020) floating dock that affords easy access for swimming and kayaking. A canoe and kayaks are available for guest use and there are amazing sunsets as well.

Guesthouse in Stevensville

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.

Home in Chestertown

4.69 out of 5 average rating, 32 reviews

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.

Home in Rock Hall

5 out of 5 average rating, 3 reviews

Pilot House

Pilot House at the Inn at Haven Harbour. Three bedrooms (two king beds, twin trundle bed) two-and-a-half baths, two large sitting rooms, full kitchen (stocked) with dining area and laundry. Guests staying at Pilot House enjoy access to all Haven Harbour Marina Resorts amenities, including three pools, private beach areas, fitness room, kayaks, paddleboards, bikes, lawn games, on-site bar and grill and more. Daily continental breakfast provided.

Private room in Stevensville

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 room in Stevensville

Fleur de Lis-BlueHeronLandingB&B

KING SUITE w sitting room and waterfront balcony A lavish second-floor haven, this King suite boasts a private spa-like bathroom with double sinks, a jacuzzi soaking tub, separate shower, and water closet. A walk-in closet, TV, and a private sitting room with workspace add convenience. Take in the Bay breezes and stunning views from the waterfront balcony. Enjoy the refined comfort and style. (840 sq ft)

Private room in Stevensville

4.97 out of 5 average rating, 76 reviews

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.

Private room in Stevensville

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)

Top Guest favourite

Private room in Millington

5 out of 5 average rating, 270 reviews

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.