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A sunset over a lake with a dock and a small settlement.

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    Check prices for these dates

    Check prices for these dates, 14 – 15 December 2026

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    Our top choices for Princess Anne cottages

    1. Key West Cottages

    A waterfront house with a balcony, dock, and a view of the water.

    2. 6 Mi to Salisbury: Forest-view Sanctuary!

    Front of property

    3. Pet-friendly creekside cottage w/ backyard

    Welcome to Creekside Retreat!

    4. Creekside Cottage with Sunroom and Fire Pit - with Plenty of Outdoor Space Near Assateague Island in Chincoteague, VA

    Exterior

    5. Deal Island Bay Cabin

    A single-story house with a front porch, a staircase leading to the entrance, and a small deck.

    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.

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    Learn more about Princess Anne

    Explore the historic Teackle Mansion with its Federal-style architecture and period furnishings that showcase Eastern Shore heritage. Visit the University of Maryland Eastern Shore campus for cultural events or take a short trip to nearby Salisbury for the Ward Museum of Wildfowl Art.

    See all hotels in Princess Anne

    A sunset over a lake with a dock and a small settlement.

    Frequently Asked Questions

    Why book your cottage in Princess Anne with Expedia?

    We think a getaway should be a piece of cake, so if you're chasing cottages in Princess Anne at a competitive price, Expedia has you covered. Save money and choose a cheap option far from the rush of the city, or splurge on a luxury cottage to pamper your favourite people.

    How can I find cheap cottages in Princess Anne?

    Expedia can help you track down cheap cottages in Princess Anne. To lock in the perfect stay in just a few keystrokes, simply use our convenient filter tool to refine your search results by star rating, budget and amenities.

    What is there to do in Princess Anne near my cottage?

    The ideal travel accessory is a well-thought-out travel plan. Hytche athletic Centre is a wonderful place to kick off your exploration of Princess Anne.