We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Homes in Deal Island

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    R 3 765 Average
    |||
    |||
    R 0R 14 000+
    Suitability
    More filters
    Don't let other travellers get your favourite Deal Island area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 17 Rentals in Deal Island
    Sort by:
    Default
    Deal Island
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    The following rentals are within 30 kilometres of Deal Island.
    Best kept secret by the bay (Entire House)1 / 20
    (4)Excellent
    Fishing Creek
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Barbara's Villa on the Pocomoke River - A Splendid Riverfront Single Family Home1 / 28
    (9)Excellent
    Rehobeth
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Chesapeake Bay Waterfront on Hoopers Island with Private Beach1 / 32
    (1)Very good
    Fishing Creek
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Parking
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely home offers all the comforts of home, including a covered porch where you can meditate, read, paint, bird watch and get away from it all, as the quiet natural beauty of the area makes it the perfect retreat! The house features spectacular views of the bay and sunsets from the first...
    View all property information
    Location Information
    21634, Fishing Creek, Maryland
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    Water water everywhere in this gorgeous home1 / 21
    (3)Very good
    Chance
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Internet Access
    • Washer
    • DVD Player
    • Porch
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 2016
    Absolutely exceeded our expectations. Plenty of room and all the comforts of home. enjoyed looking at the pictures of construction as it progressed from a small bungalow to...
    Reviewed 9 November 2014
    The home was perfect. Panoramic view of the bay. Plenty of room for a family of 8. The only fault, which isn't terrible is the shower water smells of sulfur. I would...
    See all reviews
    About this property
    Ready for rest and relaxation and/or fun and play on the water? This house in Chance, MD, has views of the Tangier Sound (part of the Chesapeake) that are downright stunning. it also has magnificent views of Haines Pond, where you will see osprey and other birds. The house has three levels....
    View all property information
    Location Information
    21821, Chance, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Fishing Creek
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Housekeeping Included
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious Historic Home. Wide open water views on both sides of the house! Come to discover 'Hoopers Hill'. Relax between waterfront sunrise and waterfront sunset. Gourmet kitchen, private beach, starry evening skies, and quiet reading spaces await. Shoreline crabbing, oystering and fishing too....
    View all property information
    Location Information
    21634, Fishing Creek, Maryland
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Vacation On The Eastern Shore1 / 17
    (1)Very good
    Hebron
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2018
    We had a great week at this home. Shared with another family as we were attending a youth baseball tournament. The house was less than 10 minutes from he fields which allowed...
    See all reviews
    About this property
    Be in the center of it all with this country house on the Eastern Shore near Salisbury, MD. 3 bedroom, 2.5 bathrooms on an acre of land with vaulted living room, two-sided fireplace, very large dining room and kitchen, deck, and your own above ground 27 foot pool! Linens and bath towels provided...
    View all property information
    Location Information
    21830, Hebron, Maryland
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Secluded Private Mansion Estate's 'Bayhouse'1 / 24
    (1)Excellent
    Marion Station
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 2018
    Excellent service. Great property to vacation with family. Gorgeous view of the bay and off the entire property and surroundings. Great service from the hostess were very...
    See all reviews
    About this property
    Bayhouse is an exclusive private dwelling located near Crisfield, Maryland. It is part of the Kingsbay Mansion Estate and sits on the shores of Coulbourne Creek at the mouth of Tangier Sound on the Chesapeake Bay. This five-bedroom residence contains a cherry paneled great room with large...
    View all property information
    Location Information
    21838, Marion Station, Maryland
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    Marion Station
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This private waterfront cottage/chalet can sleep 4 adults. This loft space has a great room with a full gourmet kitchen & new stainless steel appliances and granite counter tops. The vaulted ceiling glows with blue LED lighting that shines from ice blue ceiling beams that extend into the bedroom....
    View all property information
    Location Information
    21838, Marion Station, Maryland
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Hoopers Island Studio, 360 Degrees WATER VIEWS1 / 38
    (3)Excellent
    Fishing Creek
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 January 2018
    Memories of the peace, beauty and comfort of Fishing Creek, Maryland and of the sparkling, colorful Queen Anne Cottage that is Hoopers Island Haven warm my cold winter days! If...
    Reviewed 12 August 2014
    We came to this historic area to do some fishing. The house was well equipped with emphasis to detail. A great deal of creativity is evident once you step inside. You find...
    See all reviews
    About this property
    360 Degree Views, WATERFRONT Scenic, peaceful and spacious studio apartment located on the entire second floor of our property. AVAILABLE FOR 2 NIGHT STAY MINIMUM, sorry NO EXCEPTIONS 3rd person $25 extra per night *Ironman/Eagleman/Event/Holiday: 3 Night minimum Discounted weekly rates....
    View all property information
    Location Information
    21634, Fishing Creek, Maryland
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Save time - get the best Deal Island rentals sent straight to your email!
    Get the List
    Westover
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    • Porch
    • Waterfront
    • Shared Garden
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Frenchtown, MD, 30 min south of Salisbury, MD on Chesapeake Bay's Eastern Shore. This is a private home on an island in the middle of ten thousand acres of salt marsh and near a national wildlife management area. Views from the bedroom, enjoy waterfront sunrises, water views from the...
    View all property information
    Location Information
    21871, Westover, Maryland
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Marion Station
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kingsbay Mansion is the experience of a lifetime for those who seek quiet luxury and executive level service. Each of the five premium suites have appointments that include king beds, stunning furnishings and décor. The West Wing Room actually is a 5 bedroom 3 full bath Quest House with full use of...
    View all property information
    Location Information
    21838, Marion Station, Maryland
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    Make Enquiry
    Marion Station
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kingsbay Waterside Retreat is an elegant, modern, waterfront compound and definitely one of a kind. Located on Maryland’s Eastern Shore, Waterside is situated on the peninsula of Coulbourn Creek at the mouth of the Chesapeake Bay just north of Crisfield Maryland. Recently purchased by the owners of...
    View all property information
    Location Information
    21838, Marion Station, Maryland
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Princess Anne
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bed & Breakfast 1 Bedroom w/ bathroom. This bedroom is beautifully decorated as the Jane Austen room, its so cosy you immediately feel at home. Our peaceful and beautiful reading parlor is filled with books to enjoy. Whether you need time away from home, a romantic retreat, girlfriends retreat,...
    View all property information
    Location Information
    21853, Princess Anne, Maryland
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Princess Anne
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bed & Breakfast 1 Bedroom w/ bathroom. This bedroom is beautifully decorated, Robert L. Stevenson room is so cosy you immediately feel at home. Our peaceful and beautiful reading parlor is filled with books to enjoy. Whether you need time away from home, a romantic retreat, girlfriends retreat,...
    View all property information
    Location Information
    21853, Princess Anne, Maryland
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Princess Anne
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bed & Breakfast 1 Bedroom w/ bathroom. This bedroom is beautifully decorated as the Langston Hughes room, its so cosy you immediately feel at home. Our peaceful and beautiful reading parlor is filled with books to enjoy. Whether you need time away from home, a romantic retreat, girlfriends...
    View all property information
    Location Information
    21853, Princess Anne, Maryland
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Fishing Creek
    7 Bedrooms, 3 Bathrooms, Sleeps 17 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The historic Queen Anne Victorian vacation rental home is the perfect, quiet respite for friends and family. With 7 bedrooms, 2.5 baths, and views of the Chesapeake Bay from almost every window, this scenic home is perfect for up to 17 guests looking to getaway. Updates and amenities provide...
    View all property information
    Location Information
    21634, Fishing Creek, Maryland
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 17
    Make Enquiry
    List your property
    Owner log in