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!
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Cambridge
With a stay at this vacation home in Cambridge, you'll be on the waterfront, and 6.3 mi (10.2 km) from Ragged Island and 7.7 mi (12.4 km) from Spocott ...
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
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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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
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
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

Lusby
Located in Lusby, this vacation home is by the ocean, a 4-minute drive from Drum Point Lake and 5 minutes from Seahorse Beach.
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford
Located in Woolford, this vacation home is in a rural location, within a 10-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman State Park ...
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
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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
201 Holiday Homes
Lowest Price
AU$98
Highest Price
AU$364
Popular accommodation
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!, Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC, 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, Belle of the Chesapeake Bay, Waterfront Lusby Retreat w/ Deep-Water Dock & Slip, The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

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$364 per night from 12 Feb to 13 Feb
AU$364
includes taxes & fees
12 Feb - 13 Feb
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$196 per night from 2 Feb to 3 Feb
AU$196
includes taxes & fees
2 Feb - 3 Feb
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$206 per night from 26 Jan to 27 Jan
AU$206
includes taxes & fees
26 Jan - 27 Jan
With a stay at Springhill Suites by Marriott Prince Frederick in Prince Frederick, you'll be a 1-minute walk from R&J's PlayPark and 7 minutes by foot from calvART ...
Springhill Suites by Marriott Prince Frederick
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Days Inn & Suites by Wyndham Cambridge

Days Inn & Suites by Wyndham Cambridge

2.5 out of 5
2917 Ocean Gateway, Rt.50 East, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is AU$98 per night from 25 Jan to 26 Jan
AU$98
includes taxes & fees
25 Jan - 26 Jan
When you stay at Days Inn & Suites by Wyndham Cambridge in Cambridge, you'll be near the beach, within a 5-minute drive of Bay Country Shop and Eastern Shore ...
Days Inn & Suites by Wyndham Cambridge
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.