Book Holiday Homes in Taylors Island

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Featured Holiday Homes in Taylors Island

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

St Leonard
With a stay at this vacation home in St. Leonard, you'll be near the beach, just steps from Jefferson Patterson Park and Museum and a 3-minute drive from Perigeaux ...
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
RANCH AT ROYAL OAK- Exclusive waterfront pool pier

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Royal Oak
With a stay at this vacation home in Royal Oak, you'll be on the waterfront, and 8.3 mi (13.3 km) from St. Michaels Winery and 8.4 mi (13.6 km) from St. Michaels ...
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Beautiful Peaceful Home

Beautiful Peaceful Home

Cambridge
With a stay at this vacation home in Cambridge, you'll be within a 5-minute drive of Richardson Maritime Museum and Harriet Tubman Museum and Educational ...
Beautiful Peaceful Home
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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 Cambridge Gem w/ Hot Tub, Pool & Dock!

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Cambridge
When you stay at this vacation home in Cambridge, you'll be on the waterfront and 12 minutes by car from Spocott Windmill.
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
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 Battle Creek Cypress Swamp Sanctuary.
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
The Normandy Cottage ~ Charming Getaway ~  On The Shores Of The Chesapeake!

The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!

North Beach
Located in North Beach, this vacation home is by the sea, a 3-minute walk from Bayside History Museum and within a 5-minute drive of Chesapeake Beach Water ...
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

Lusby
Located in Lusby, this vacation home is on the waterfront, within a 15-minute drive of Calvert Cliffs State Park and Annmarie Sculpture Garden and Arts ...
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat
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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
202 Holiday Homes
Lowest Price
AU$162
Highest Price
AU$365
Popular accommodation
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!, RANCH AT ROYAL OAK- Exclusive waterfront pool pier, Beautiful Peaceful Home, The Blue Crab Beach House - Free beach passes , Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, The Lazy Crab Beach House - Free beach passes , The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake! , Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

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$365 per night from 13 Jan to 14 Jan
AU$365
includes taxes & fees
13 Jan - 14 Jan 2025
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

3 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Fully refundableReserve now, pay when you stay
The price is AU$208 per night from 5 Jan to 6 Jan
AU$208
includes taxes & fees
5 Jan - 6 Jan 2025
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
Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick

3 out of 5
75 Sherry Lane, Prince Frederick, MD
Fully refundableReserve now, pay when you stay
The price is AU$180 per night from 26 Dec to 27 Dec
AU$180
includes taxes & fees
26 Dec - 27 Dec
Located in Prince Frederick, Springhill Suites by Marriott Prince Frederick is within a 10-minute drive of Running Hare Vineyard and Patuxent River.
Springhill Suites by Marriott Prince Frederick
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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$162 per night from 25 Dec to 26 Dec
AU$162
includes taxes & fees
25 Dec - 26 Dec
Located in California, La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent is within a 5-minute drive of Patuxent River Naval Air Museum and Patuxent ...
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
Don't see what you're looking for?
See all available properties in Taylors Island
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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.