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Featured Holiday Homes in Taylors Island

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
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!
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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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!
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
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
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
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

St. Michaels
Located in St. Michaels, this vacation home is on the waterfront, within a 10-minute drive of Saint Michaels Village and St. Michaels Winery.
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock
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
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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
197 Holiday Homes
Lowest Price
AU$110
Highest Price
AU$430
Popular accommodation
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!, Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC, Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!, The Blue Crab Beach House - Free beach passes , The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, Waterfront Lusby Retreat w/ Deep-Water Dock & Slip, Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock, Belle of the Chesapeake Bay

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$430 per night from 25 Feb to 26 Feb
AU$430
includes taxes & fees
25 Feb - 26 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

4 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Fully refundableReserve now, pay when you stay
The price is AU$234 per night from 9 Mar to 10 Mar
AU$234
includes taxes & fees
9 Mar - 10 Mar
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
The price is AU$162 per night from 16 Mar to 17 Mar
AU$162
includes taxes & fees
16 Mar - 17 Mar
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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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$110 per night from 26 Feb to 27 Feb
AU$110
includes taxes & fees
26 Feb - 27 Feb
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
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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.