Book Holiday Homes in Taylors Island
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Featured Holiday Homes in Taylors Island

Waterfront Wildlife Retreat on the Patuxent River

The Blue Crab Beach House - Free beach passes

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Beach Home with King Bed and Beach Passes in a Cute Town

Rising Sun Bay View Cottage

Belle of the Chesapeake Bay

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
Taylors Island Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Taylors Island vacation homes are the perfect way for you to wing it.
Holiday houses in Taylors Island let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Taylors Island in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Taylors Island adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Taylors Island with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Taylors Island vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Taylors Island Holiday Homes essential information
Accommodation | 262 Holiday Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | Waterfront Wildlife Retreat on the Patuxent River , The Blue Crab Beach House - Free beach passes , The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, Beach Home with King Bed and Beach Passes in a Cute Town, Rising Sun Bay View Cottage, Belle of the Chesapeake Bay, Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!, Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants |
Top trending hotels in Taylors Island

Hyatt Regency Chesapeake Bay

Solomons Inn Resort & Marina

Rod 'N' Reel Resort

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
More ways to explore Taylors Island
Top picks
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^Subject to availability and chosen travel dates.