Book Holiday Homes in Taylors Island

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Featured Holiday Homes in Taylors Island

The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach MD
Located in Owings, this vacation home is within a 5-minute drive of Bayside History Museum and Chesapeake Bay.
Opens in a new windowThe Cozy Crab- Your Charming Haven in Lovely North Beach!
Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

Solomons MD
The price is AU$898 per night from 24 Nov to 25 Nov
AU$898
24 Nov - 25 Nov
includes taxes & fees
A stay at this vacation home places you in the heart of Solomons, within a 5-minute walk of J.C. Lore Oyster House and Solomons Yachting Center.
Opens in a new windowSpacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge MD
The price is AU$540 per night from 8 Dec to 9 Dec
AU$540
8 Dec - 9 Dec
includes taxes & fees
A stay at this vacation home places you in the heart of Cambridge, steps from Long Wharf Park and Choptank River Lighthouse.
Opens in a new windowCozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Cambridge MD
Located in Cambridge, this vacation home is on the waterfront, within a 15-minute drive of Spocott Windmill and Richardson Maritime Museum.
Opens in a new windowNEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford MD
Located in Woolford, this vacation home is in a rural location, within a 10-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman Underground ...
Opens in a new windowThe Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Prince Frederick MD
The price is AU$532 per night from 24 Nov to 25 Nov
AU$532
24 Nov - 25 Nov
includes taxes & fees
With a stay at this vacation home in Prince Frederick, you'll be just steps from Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new window2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Shewell's A-Frame on Mill Creek

Shewell's A-Frame on Mill Creek

Lusby MD
Located in Lusby, this vacation home is within a 5-minute drive of Drum Point Lake and Chesapeake Bay.
Opens in a new windowShewell's A-Frame on Mill Creek
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 MD
When you a stay at this vacation home in Port Republic, you'll be on the beach, just steps from Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowStunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Discover tranquility near Calvert Cliffs

Discover tranquility near Calvert Cliffs

Saint Leonard MD
Located in St. Leonard, this vacation home is on the waterfront, within a 10-minute drive of Perigeaux Vineyards and Winery and Jefferson Patterson Park and ...
Opens in a new windowDiscover tranquility near Calvert Cliffs
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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
248 Holiday Homes
Lowest Price
AU$163
Highest Price
AU$898
Popular accommodation
The Cozy Crab- Your Charming Haven in Lovely North Beach!, Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops, Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock, The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!, Shewell's A-Frame on Mill Creek, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, Discover tranquility near Calvert Cliffs

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$324 per night from 17 Dec to 18 Dec
AU$324
17 Dec - 18 Dec
includes taxes & fees
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 5 minutes from Meredith House.
Opens in a new windowHyatt 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$185 per night from 23 Nov to 24 Nov
AU$185
23 Nov - 24 Nov
includes taxes & fees
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 ...
Opens in a new windowRod 'N' Reel Resort
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$183 per night from 23 Nov to 24 Nov
AU$183
23 Nov - 24 Nov
includes taxes & fees
With a stay at Solomons Inn Resort & Marina in Solomons, you'll be a 3-minute walk from Southern Branch Library and 11 minutes by foot from Drum Point ...
Opens in a new windowSolomons Inn Resort & Marina
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La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

3 out of 5
22769 Three Notch Rd California MD
Fully refundableReserve now, pay when you stay
The price is AU$163 per night from 23 Nov to 24 Nov
AU$163
23 Nov - 24 Nov
includes taxes & fees
Located in California, La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent is within a 5-minute drive of San Souci Shopping Center and Dunleigh Neighborhood ...
Opens in a new windowLa Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
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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.