Book Holiday Homes in Taylors Island

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Featured Holiday Homes in Taylors Island

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island MD
When you stay at this vacation home in Tilghman, you'll be on the waterfront, within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowWaterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
The Cozy Crab- Your Charming Haven in Lovely North Beach!

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

North Beach MD
With a stay at this vacation home in Owings, you'll be within a 5-minute drive of Chesapeake Bay and Bayside History Museum.
Opens in a new windowThe Cozy Crab- Your Charming Haven in Lovely North Beach!
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Cambridge MD
With a stay at this vacation home in Cambridge, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Spocott Windmill.
Opens in a new windowWaterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
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The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes

North Beach MD
When you stay at this vacation home in North Beach, you'll be by the sea, within a 10-minute walk of Chesapeake Bay and Bayside History Museum.
Opens in a new windowThe Blue Crab Beach House - Free beach passes
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Lusby MD
With a stay at this vacation home in Lusby, you'll be on a lake, within a 10-minute drive of Chesapeake Bay and Cove Point Park.
Opens in a new windowBay view from Calvert Cliffs, Solomons Island & State Park nearby
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

St. Michaels MD
Located in St. Michaels, this vacation home is on the waterfront, within a 10-minute drive of St Michaels Nature Trail and Higgins Yacht Yard and Marina.
Opens in a new windowMinutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
Back Creek Villa Covered Deck

Back Creek Villa Covered Deck

Solomons MD
With a stay at this vacation home in Solomons Island, you'll be within a 15-minute drive of Chesapeake Bay and J.C. Lore Oyster House.
Opens in a new windowBack Creek Villa Covered Deck
Charming 2-bedroom Cap Cod style cottage

Charming 2-bedroom Cap Cod style cottage

California MD
Located in Great Mills, this vacation home is within a 5-minute drive of San Souci Shopping Center and Dunleigh Neighborhood Park.
Opens in a new windowCharming 2-bedroom Cap Cod style cottage
4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick

4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick

Prince Frederick MD
With a stay at this vacation home in Prince Frederick, you'll be within a 15-minute drive of Chesapeake Bay and King Memorial Park.
Opens in a new window4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick
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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
253 Holiday Homes
Lowest Price
AU$139
Highest Price
AU$408
Popular accommodation
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets, The Cozy Crab- Your Charming Haven in Lovely North Beach!, Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, The Blue Crab Beach House - Free beach passes , Bay view from Calvert Cliffs, Solomons Island & State Park nearby, Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock, Back Creek Villa Covered Deck, Charming 2-bedroom Cap Cod style cottage, 4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick

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$408 per night from 17 May to 18 May
AU$408
17 May - 18 May
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 Eastern Shore Hospital ...
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$223 per night from 25 May to 26 May
AU$223
25 May - 26 May
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 Rod n Reel Charter ...
Opens in a new windowRod 'N' Reel Resort
avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG

3 out of 5
23274 Three Notch Road California MD
Fully refundable
The price is AU$162 per night from 25 May to 26 May
AU$162
25 May - 26 May
includes taxes & fees
Located in California, avid hotel California - Lexington Park by IHG is in the historical district, within a 5-minute drive of Wildewood Shopping Center and ...
Opens in a new windowavid hotel California - Lexington Park by IHG
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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$139 per night from 24 May to 25 May
AU$139
24 May - 25 May
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
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.

Top Picks

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^Subject to availability and chosen travel dates.