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 Rentals and Homes in Taylors Island, MD

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    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}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 18 Rentals in the Taylors Island Area
    loading...
    Don't let other travellers get your favourite Taylors Island area holiday rental. You're so close to securing your perfect getaway. Book today.
    Sort by

    The following rentals are within 30 kilometers of Taylors Island, Maryland.

    From
    €122
    / Night
    Payment Protection
    View Details
    1 / 57
    5 of 5 stars (2) Excellent
    Fishing Creek
    1 Bedroom / 1 Bathroom / Sleeps 3
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    From
    €364
    / Night
    Payment Protection
    View Details
    1 / 29
    Lusby
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
    Overview Make Enquiry
    From
    €159
    / Night
    Payment Protection
    View Details
    1 / 20
    5 of 5 stars (4) Excellent
    Tilghman
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    From
    €82
    / Night
    Payment Protection
    View Details
    1 / 40
    3.5 of 5 stars (3) Average
    Trappe
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Internet Access
    • DVD Player
    • Watersports Nearby
    • Private Fishing...
    • TV
    • Waterfront
    • Water Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Beautiful, serene waterfront home on the Chesapeake Bay. One hour from the Atlantic Ocean (Ocean City, Assateague Island) and Annapolis, One and a half hours from Washington DC and Baltimore. Many nearby places worth visiting, including picturesque St. Michaels and the Blackwater Wildlife Refuge... View all property information
    Make Enquiry
    Location Information
    Trappe, Talbot County 21673
    1 of 5 stars Reviewed 7 July 2015
    I never write a review for good or bad experiences but I could not let this one go. Dimitri was very friendly in the exchange of information before arriving to the house. The only...
    5 of 5 stars Reviewed 26 August 2014
    Beautiful home and view of the bay. Private beach was amazing. Perfect for a group of friends or a couple looking to get away. I will definitely be staying here again!
    See all reviews
    From
    €114
    / Night
    Payment Protection
    View Details
    1 / 21
    Tilghman
    2 Bedrooms / 1 Bathroom / Sleeps 6
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Get away and stay in our cozy cottage that sits on the Knapp's Narrows in Tilghman, MD. Captain's Watch is a Waterfront Cottage which has a screened porch with beautiful sunrise view of Knapps Narrows. It is nestled in a Working Watermens Village, 12 miles from Historic St. Michaels, Maryland on... View all property information
    Make Enquiry
    Location Information
    Tilghman, Talbot County 21671
    From
    €237
    / Night
    Payment Protection
    View Details
    1 / 10
    Saint Leonard
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Waterfront
    • Internet Access
    • Stereo System
    • Deck
    • Air Conditioning
    • Water Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Looking for a peaceful beach getaway? Located in quiet Long Beach overlooking Flag Harbor Yacht Haven marina, this cottage is a few minutes walk to the sandy beach along cliffs famous for fossils from the Miocene. The shallow water is safe for children to swim, and a favorite for fishermen and... View all property information
    Make Enquiry
    Location Information
    Saint Leonard, Calvert County 20685
    From
    €228
    / Night
    Payment Protection
    View Details
    1 / 5
    3 of 5 stars (1) Average
    Cambridge
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Charming, historic home in the Neck District, Maryland's most beautiful, unspoiled area. This adorable east-facing 100-year-old home sits on a generous lot (over an acre) with forever waterviews, mature shade trees, flowering perennials, roses, large fenced vegetable garden, breezy patio, wide... View all property information
    Make Enquiry
    Location Information
    Cambridge, Maryland 21613
    From
    €228
    / Night
    Payment Protection
    View Details
    1 / 17
    Tilghman
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • There Are Tennis...
    • Ocean Views
    • Wi-Fi
    • Water Views
    • Watersports Nearby
    • Satellite TV
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in the heart of the classic waterman's village of Tilghman Island, this gorgeous Knapps Narrows waterfront home comes complete with a boat slip! Watch the boats stream by, fish, crab or just relax in this 2700 sq ft home. This stunning vacation home boasts an open floor-plan, gourmet... View all property information
    Make Enquiry
    Location Information
    Tilghman, Talbot County 21671
    From
    €145
    / Night
    Payment Protection
    View Details
    1 / 20
    Fishing Creek
    3 Bedrooms / 2 Bathrooms / Sleeps 5
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Private Fishing...
    • Housekeeping...
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Pool Table
    • Game Room
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Hooper's Island is located between the Honga River and Chesapeake Bay on Marylands Eastern Shore. This unique island is a 'MUST DO' on your bucket list. Especially noted for: Maryland's famous Blue Crabs and Breathtaking Sunsets!!! April thru October on Hooper's Island is must do on your... View all property information
    Make Enquiry
    Location Information
    Fishing Creek, Maryland 21634
    From
    €456
    / Night
    View Details
    1 / 18
    4.5 of 5 stars (7) Very good
    Cambridge
    6 Bedrooms / 3 Bathrooms / Sleeps 18
    Overview Reviews (7) Make Enquiry
    Amenities & Details
    • Watersports Nearby
    • Waterfront
    • DVD Player
    • Internet Access
    • Water Views
    • Boat Available
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    The Swan's Nest in Cambridge, Maryland, has all that the Chesapeake Bay has to offer: sun, sand, fishing, crabbing,and so much more. The spacious and lovingly restored farmhouse can accommodate 18 guests. The kitchen is fully equipped and a barbeque pit is just outside on the patio. Bring your... View all property information
    Make Enquiry
    Location Information
    Cambridge, Maryland 21613
    1 of 5 stars Reviewed 19 July 2015
    We stayed at Swan's Nest for 1 week starting on June 27, 2015, and contrary to the glowing reviews here, this is what we found: -The house was supposed to have 6 bedrooms...
    5 of 5 stars Reviewed 7 October 2014
    So enjoyed this beautiful farm house with all amenities. So pleasantly surprised that everything was just perfect. Did not want to expect what we normally expect when we travel...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    €1,185
    / Night
    View Details
    1 / 22
    5 of 5 stars (5) Excellent
    Cambridge
    7 Bedrooms / 6 Bathrooms / Sleeps 28
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Private Fishing...
    • Internet Access
    • Hot Tub
    • Waterfront
    • Playground
    • Air Conditioning
    • Satellite TV
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Experience the lavish surroundings of Captain's Quarters. Whether your pleasure is sailing, fishing, water sports, relaxing by the pool and jacuzzi or nestling up on the veranda with a good book, Captain's Quarter's provides luxury around every corner. This unrivaled waterfront estate accommodates... View all property information
    Make Enquiry
    Location Information
    Cambridge, Maryland 21613
    5 of 5 stars Reviewed 21 May 2014
    I had my wedding at this property. The landlord, Frank, was very polite and easy going. He allowed for our dogs to stay for a low fee and was very good at returning calls. The...
    5 of 5 stars Reviewed 3 August 2012
    I would not change a single thing. Our family enjoyed the six day stay at this awesome place. The amenities were great, the location was central to other sights, and the...
    See all reviews
    From
    €1,093
    / Night
    View Details
    1 / 42
    5 of 5 stars (2) Excellent
    Cambridge
    5 Bedrooms / 4 Bathrooms / Sleeps 18
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Playground
    • Satellite TV
    • DVD Player
    • Waterfront
    • Shared Outdoor Pool...
    • Internet Access
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Swan Cove awaits your family vacation or group! It's also an ideal place for a most memorable wedding. This incredible, newly redesigned waterfront home with a private dock offers spectacular views with a large swimming pool, 4 kayaks, outdoor firepit (firewood is furnished), playground and a large... View all property information
    Make Enquiry
    Location Information
    Cambridge, Maryland 21613
    From
    €409
    / Night
    View Details
    1 / 27
    4.5 of 5 stars (11) Very good
    Cambridge
    7 Bedrooms / 5 Bathrooms / Sleeps 18
    Overview Reviews (11) Make Enquiry
    Amenities & Details
    • Waterfront
    • Private Outdoor...
    • Satellite TV
    • Water Views
    • Air Conditioning
    • Hot Tub
    • Private Fishing...
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    New premier waterfront vacation home - 6bed / 5bath home w/ beach & private pool. All of this on over 3 acres and +- 400 feet of stunning waterfront Near Cambridge Maryland, also Easton, St. Michaels and Oxford. The den also serves as an additional bdrm with full bath making it 7bdrms. Ideal... View all property information
    Make Enquiry
    Location Information
    Cambridge, Maryland 21613
    5 of 5 stars Reviewed 29 October 2014
    The Ideal Family Vacation This summer, our family decided to try something different and rent a house on the eastern shore of Maryland. After spending a day reconnoitering a...
    4 of 5 stars Reviewed 12 October 2014
    Really excellent location by the water, and the pool adds additional options. House itself is large, and is great for 2-3 families with kids. We were a group of friends, which...
    See all reviews
    From
    €409
    / Night
    View Details
    1 / 30
    4.5 of 5 stars (11) Very good
    Cambridge
    6 Bedrooms / 5 Bathrooms / Sleeps 16
    Overview Reviews (11) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Hot Tub
    • Private Fishing...
    • Internet Access
    • Sauna
    • Satellite TV
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Fabulous, recently-built premier vacation home on 500 feet of Chesapeake waterfront. A gorgeous home; beach, dock, private pool, boats, bikes, porches & mile-wide view With 6 acres of property, wide water & sandy beaches, this private luxury vacation rental is minutes from Cambridge,... View all property information
    Make Enquiry
    Location Information
    Cambridge, Maryland 21677
    5 of 5 stars Reviewed 14 July 2015
    This was a perfect setting for our family vacation. Our grandkids ages range from 4-17 and they all enjoyed biking, kayaking, swimming, fishing and playing in the sand. The...
    5 of 5 stars Reviewed 27 June 2015
    Our extended family (22 people - 13A/9K) had a great week at Saddle Beach. The house was beautiful and in very good condition. The option of being in the pool or the river...
    See all reviews
    From
    €780
    / Night
    View Details
    1 / 29
    Trappe
    8 Bedrooms / 6 Bathrooms / Sleeps 16
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Private Fishing...
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Water Views
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Martins Point is a late 18th Century house and cottages on Maryland's historic Eastern Shore where the Underground Railroad once passed through the property. It is located on a secluded finger of land, surrounded by water on three sides, a place to unwind, immerse yourself in the natural beauty of... View all property information
    Make Enquiry
    Location Information
    Trappe, Talbot County 21673
    From
    €109
    / Night
    View Details
    1 / 11
    Lusby
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Fireplace
    • Air Conditioning
    • Stereo System
    • Deck
    • Satellite TV
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Lovely year round rental cottage situated on almost one acre within a few minutes walk to one of the longest private beaches on the western shore of the Chesapeake Bay. Enjoy walking the mile beach to the historic Cove Point Lighthouse collecting sea shells or hunting for fossils, especially... View all property information
    Make Enquiry
    Location Information
    Lusby, Calvert County 20657
    From
    €273
    / Night
    View Details
    1 / 8
    Lusby
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Stereo System
    • Fireplace
    • Internet Access
    • Deck
    • Washer
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Cedar Beach Lodge is a modern, smoke free, year-round retreat located in the desirable and private Cove Point Beach Community on the western shore of the Chesapeake Bay. It is conveniently located 1 hour from Annapolis, MD and Washington, DC on Route 4 and 10 minutes from Solomon's Island, MD.... View all property information
    Make Enquiry
    Location Information
    Lusby, Calvert County 20657
    From
    €820
    / Week
    View Details
    1 / 40
    Cambridge
    3 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • TV
    • Hot Tub
    • Deck
    • Air Conditioning
    • Grill
    • Waterfront
    • DVD Player
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    'The Cottage' at Heron Cove is a cozy home situated on a scenic peninsula with water views from every window. Awake each morning to watch the sun glisten off the gentle waters. Explore ten acres of land and 1000 feet of shoreline. Relax on the wrap around screened in porch or soak in the 450 gallon... View all property information
    Make Enquiry
    Location Information
    Cambridge, Maryland 21613