Plan your trip

A beach with several boats and people fishing.

Search Deal Island Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

  • Find vacation rentals that suit your style

    Cottages

    Cabins

    Apartments

    Condos

    Check prices for these dates

    Check prices for these dates, December 13 – 14, 2026

    View in a map

    Our top choices for Deal Island cottages

    1. 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.

    View all properties

    Learn more about Deal Island

    Watermen's heritage tours reveal the authentic Chesapeake Bay lifestyle while you learn about the island's historic skipjack fleet. Explore pristine marshlands by kayak or visit the Deal Island Wildlife Management Area where birdwatchers spot rare migratory species.

    See all hotels in Deal Island

    A beach with several boats and people fishing.

    Top reviews in Deal Island

    The Whitehaven Hotel

    A large, historic house with a wrap-around porch and a gazebo, surrounded by lush vegetation and a body of water.

    Rodeway Inn at Somers Cove Marina

    A covered walkway with a brick wall and a metal railing.

    Hampton Inn & Suites Salisbury/Fruitland

    A Hampton Inn & Suites with a covered entrance, brick facade, and well-maintained landscaping.

    Best Western Plus Pocomoke City

    A multi-story hotel with a brick facade, large windows, and a covered entrance area.

    Americas Best Value Inn Princess Anne

    A yellow motel with a sign reading "Best UFO" and a car parked in front.

    Econo Lodge Princess Anne

    A hotel entrance with a large sign reading "EconoLodge," a covered walkway, and a landscaped area with bushes.

    Frequently Asked Questions

    Why book your cottage in Deal Island with Expedia?

    We think that a vacay should be stress-free, so if you're seeking cottages in Deal Island at a nice price, Expedia has got your back. Keep the budget in check and opt for a thrifty option surrounded by nature, or book a 5-star cottage to really spoil your favorite people.

    How can I find cheap cottages in Deal Island?

    Expedia can help you easily source cheap cottages in Deal Island. To lock in your perfect stay in a few quick clicks, try out our convenient filter tool to tailor your search results by budget, amenities and star rating.

    Explore a world of travel with Expedia