Book Holiday Homes in Taylors Island

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Featured Holiday Homes in Taylors Island

The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes

North Beach
Located in North Beach, this vacation home is by the sea, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water Park.
The Blue Crab Beach House - Free beach passes
Waterfront Wildlife Retreat on the Patuxent River

Waterfront Wildlife Retreat on the Patuxent River

Lusby
Located in Lusby, this vacation home is on the waterfront, a 4-minute drive from Drum Point Lake and 6 minutes from Seahorse Beach.
Waterfront Wildlife Retreat on the Patuxent River
Modern Waterfront House with Amazing views!

Modern Waterfront House with Amazing views!

North Beach
Located in North Beach, this vacation home is on the waterfront, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water Park.
Modern Waterfront House with Amazing views!
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Sweet Bamboo Beach Cottage

Sweet Bamboo Beach Cottage

north beach
When you stay at this vacation home in North Beach, you'll be on the beach, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water ...
Sweet Bamboo Beach Cottage
Stunning  Chesapeake view from almost ever room, private  15 home community beach, fossils, 450 pier

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Port Republic
Located in Port Republic, this vacation home is on the waterfront, within a 10-minute drive of R&J's PlayPark and calvART Gallery.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
The Lazy Crab Beach House - Free beach passes

The Lazy Crab Beach House - Free beach passes

North Beach
A stay at this vacation home places you in the heart of North Beach, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water Park.
The Lazy Crab Beach House - Free beach passes
Belle of the Chesapeake Bay

Belle of the Chesapeake Bay

Lusby
When you stay at this vacation home in Lusby, you'll be within a 10-minute drive of Cove Point Park and Calvert Cliffs State Park.
Belle of the Chesapeake Bay
Tranquil  Beautiful Waterfront  Near Historic St. Michaels & Royal Oak

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

easton
With a stay at this vacation home, you'll be centrally located in Easton, within a 10-minute drive of Saint Michaels Village and St. Michaels Winery.
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2 out of 5
Cambridge
Located in Cambridge, this vacation home is within a 15-minute walk of Harriet Tubman Museum and Educational Center and Richardson Maritime Museum.
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
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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.

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
250 Holiday Homes
Lowest Price
AU$170
Highest Price
AU$457
Popular accommodation
The Blue Crab Beach House - Free beach passes , Waterfront Wildlife Retreat on the Patuxent River , Modern Waterfront House with Amazing views!, Sweet Bamboo Beach Cottage, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, The Lazy Crab Beach House - Free beach passes , Belle of the Chesapeake Bay, Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak, Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Top trending hotels in Taylors Island

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is AU$457 per night from 6 May to 7 May
AU$457
includes taxes & fees
6 May - 7 May
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 6 minutes from Dorchester County Visitors ...
Hyatt Regency Chesapeake Bay
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Fully refundableReserve now, pay when you stay
The price is AU$246 per night from 21 Apr to 22 Apr
AU$246
includes taxes & fees
21 Apr - 22 Apr
When you stay at Rod 'N' Reel Resort in Chesapeake Beach, you'll be on the waterfront, just steps from Chesapeake Beach Railway Museum and 3 minutes by foot ...
Rod 'N' Reel Resort
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

2.5 out of 5
22769 Three Notch Rd, California, MD
Fully refundableReserve now, pay when you stay
The price is AU$170 per night from 13 Apr to 14 Apr
AU$170
includes taxes & fees
13 Apr - 14 Apr
With a stay at La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent in California, you'll be within a 5-minute drive of Patuxent River Naval Air Station ...
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
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Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

2.5 out of 5
155 Holiday Dr. P.O. Box 1099, Solomons, MD
Fully refundableReserve now, pay when you stay
The price is AU$240 per night from 21 Apr to 22 Apr
AU$240
includes taxes & fees
21 Apr - 22 Apr
With a stay at Solomons Inn Resort & Marina in Solomons, you'll be within a 15-minute drive of Patuxent River Naval Air Station and Southern Branch Library.
Solomons Inn Resort & Marina
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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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^Subject to availability and chosen travel dates.