Location

Dates

Guests

Vacation rentals in Tilghman Island, Maryland, United States

Black Walnut Cove

Outdoor Seating

La Casita at Black Walnut-Waterfront Escape near Saint Michaels

3 bedrooms·1½ baths

Tilghman Island • Maryland

$ 1.006,25 USD totaal voor 3 nachten

18–21 nov 2026

Relaxing Retreat on the Hudson image 1

Relaxing Retreat on the Hudson image 2

Relaxing Retreat on the Hudson image 3

Relaxing Retreat on the Hudson image 4

Relaxing Retreat on the Hudson image 5

Relaxing Retreat on the Hudson

5 bedrooms·2 baths

Maryland

5(34 reviews)

$ 950,00 USD totaal voor 3 nachten

22–25 nov 2026

Majestic Murphy Point

Back yard launch

Front facing the bay

Kitchen/Dining open floor plan

Murphy Point on the Chesapeake Vacation Rental

3 bedrooms·1 bath

North Beach • Maryland

4.8(114 reviews)

$ 1.320,00 USD totaal voor 3 nachten

31 mrt – 3 apr 2027

Welcome to beautiful North Beach!

Cozy fire pit patio with stylish seating and outdoor dining

Cozy fire pit patio with private fenced yard and stylish outdoor seating

Palm Haven in North Beach, MD

One of two bedrooms on the ground floor, this bedroom has a queen sized bed and en-suite bathroom.

Palm Haven in North Beach, MD

4 bedrooms·3 baths

North Beach • Maryland

5(208 reviews)

$ 1.045,08 USD $ 889,68 USD totaal voor 3 nachten

22–25 nov 2026

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

3 bedrooms·2 baths

North Beach • Maryland

5(260 reviews)

$ 622,17 USD $ 540,25 USD totaal voor 3 nachten

22–25 nov 2026

Cozy Cottage By The Beach-Pet Friendly

Cozy Cottage By The Beach-Pet Friendly

Main living space.

Cozy Cottage By The Beach-Pet Friendly

Cozy Cottage By The Beach-Pet Friendly

3 bedrooms·2 baths

North Beach • Maryland

4.96(26 reviews)

$ 964,05 USD totaal voor 3 nachten

25–28 jul 2027

The Landing is a waterfront vacation home with private pool, fire pit, and spacious yard. It is family-friendly with plenty of spaces to gather. Located near Annapolis, Kent Narrows, Easton, St. Michael’s, Naval Academy, and wedding venues.

Waterfront home in Kent Island - the perfect place to stay on your vacation to Maryland’s Eastern Shore.

Firepit by the water lets you enjoy s’mores durning your stay in Stevensville, MD.

*Waterfront* 5BR w/ Pool + Firepit on Kent Island!

Cathedral ceilings with natural wood light-up this waterfront living room. This room has a dining table for 10, sofa area with electric fireplace and 65" tv and the children's playroom.

Waterfront 5BR w/ Pool + Firepit on Kent Island!

5 bedrooms·3½ baths

Stevensville • Maryland

$ 2.560,00 USD totaal voor 3 nachten

18–21 nov 2026

Off The Chart Stays Cottage

living room at entrance with gas fireplace and smart tv

Kitchen and Living room

Off The Chart Stays

2 bedrooms·2 baths

Stevensville • Maryland

5(8 reviews)

$ 1.709,40 USD totaal voor 3 nachten

18–21 nov 2026

Almost Heaven/Vibrant waterfront home with pool

4 bedrooms·3 baths

Cambridge • Maryland

5(42 reviews)

$ 1.720,00 USD totaal voor 3 nachten

8–11 mrt 2027

Hickory House on the Chesapeake Bay! image 1

Hickory House on the Chesapeake Bay! image 2

Hickory House on the Chesapeake Bay! image 4

Hickory House on the Chesapeake Bay! image 6

Bay Views, Private Beach Access and Pet Friendly!

2 bedrooms·1 bath

Saint Leonard • Maryland

4.92(88 reviews)

$ 667,00 USD totaal voor 3 nachten

18–21 nov 2026

Cozy 5-Bed Retreat, Heated Spa

Elegant brick home with glowing entry and stunning autumn curb appeal

Convenient in-home laundry room with washer, dryer, iron, and folding space

Cozy 5-Bed Retreat, Heated Spa

this is the Blue Room. The Decour is inspired by grand millennial chinoiserie. Daylight above is a remote controlled fandelier for climate comfort.

Cozy 5-Bed Retreat, Heated Spa

5 bedrooms·3½ baths

Port Republic • Maryland

4.78(58 reviews)

$ 1.735,50 USD totaal voor 3 nachten

29 nov – 2 dec 2026