Plan your trip

A pier extending into a body of water with people fishing, a clear sky, and distant land with a bridge.

Search Holiday Homes in Stevensville

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key

    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

    • Find holiday rentals that suit your style

    Apartments

    Cottages

    Condos

    Check prices for these dates

    Check prices for these dates, 13 – 14 December 2026

    View in a map

    Our top choices for Stevensville holiday homes

    1. Charming Coastal/Country Home w/3 Acres & Sauna!

    A marina with boats docked, a city skyline in the background, and a calm water surface reflecting the lights.

    2. Relax on Kent Island in 4 Bedroom Home w/Waterview

    A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

    3. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

    A beach with a wooden fence and a pier in the distance.

    4. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

    A beach with a wooden fence and a pier in the distance.

    5. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

    A two-story house with a red roof, a brick chimney, and a small porch.

    6. Family Friendly Cozy 3 Bedroom Duplex

    A kitchen with wooden cabinets, a stove, and a dining table with chairs.

    7. Large 2 bedroom house with private parking in a nice neighborhood

    A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

    8. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

    A sandy beach with lounge chairs and a small pond.

    9. Cute, Cozy 2-bedroom house near Annapolis with water access

    A sandy beach with a boat docked on the left and calm water.

    10. BAYSIDE BUNGALOW

    A house with a front porch, a pathway leading to the entrance, and a bicycle parked outside.

    11. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

    A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

    12. Annapolis Retreat - 7 mins from downtown Annapolis!

    A house with a stone facade, a white door with a glass panel, and a porch with two potted plants.

    13. Cozy 2br home w/ parking in downtown Annapolis

    A wooden dock extending into a calm body of water with boats docked at the end.

    14. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

    A two-story house with a front porch, a mailbox, and a wreath on the door.

    15. 5 bedroom house with EV charger Near Downtown Annapolis

    A backyard patio with a round table and chairs, surrounded by a gravel area.

    16. Renovated Bungalow | Walk to Beach | Dog-Friendly

    A calm lake with boats docked, a sandy shore, and houses in the background.

    17. Lower Level Loft - Adorable Studio Apt. Near BWI

    A living room with a sofa, a coffee table, a dining table with chairs, a lamp, and a beach-themed artwork on the wall.

    18. Family Home on Mayo Peninsula | Deck | Sleeps 10

    A modern kitchen with white cabinets, a microwave, and a sink. There is a dining area with a wooden table and chairs.

    19. Cute bungalow blocks to Stadium

    A modern kitchen with a central island, built-in oven, and microwave.

    20. Fabulous 5-bedroom house with AC in charming Annapolis

    A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

    View all properties

    Learn more about Stevensville

    Stroll along sandy shores at Matapeake State Park or cast a line from Romancoke Wharf County Park. Music lovers can tour Paul Reed Smith Guitars, then savour fresh seafood at local restaurants in this charming bayside town.

    See all hotels in Stevensville

    A pier extending into a body of water with people fishing, a clear sky, and distant land with a bridge.

    Top reviews in Stevensville

    The Inn at Chesapeake Bay Beach Club

    A large, multi-story building with a prominent red cylindrical tower, a covered patio area, and a well-maintained garden.

    Hyatt Place Kent Narrows & Marina

    A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

    Hilton Garden Inn Kent Island Marina

    A covered outdoor area with white wicker furniture and a view of boats in the background.

    Historic Inns of Annapolis

    A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

    The Wildset

    A bedroom with a large bed, a bedside table, a nightstand, a wall-mounted light, and a door leading to a bathroom.

    Graduate by Hilton Annapolis

    A spacious atrium with a high ceiling, skylights, and a patterned floor.

    Quality Inn Grasonville near Kent Island

    A spacious lobby with a staircase, a reception desk, and a dining area.

    Hilton Garden Inn Annapolis Downtown

    A modern lounge area with a sofa, chairs, a coffee table, and a bookshelf.

    Inn at Perry Cabin

    A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

    DoubleTree by Hilton Hotel Annapolis

    A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.

    Country Inn & Suites by Radisson, Annapolis, MD

    A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.