Book Holiday Homes in Taylors Island

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Featured Holiday Homes in Taylors Island

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
The price is AU$609 per night from 16 Dec to 17 Dec
AU$609
includes taxes & fees
16 Dec - 17 Dec
A stay at this vacation home places you in the heart of Cambridge, steps from Long Wharf Park and Choptank River Lighthouse.
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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
Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!

Cambridge
The price is AU$793 per night from 5 Dec to 6 Dec
AU$793
includes taxes & fees
5 Dec - 6 Dec
When you stay at this vacation home in Cambridge, you'll be on the waterfront and 8 minutes by car from Spocott Windmill.
Beautiful Waterfront Retreat in Cambridge!
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Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood
When you stay at this vacation home in Sherwood, you'll be on the waterfront and 7 minutes by car from Tilghman Watermen’s Museum.
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
WATERFRONT!!! The River's Roost on The Patuxent River

WATERFRONT!!! The River's Roost on The Patuxent River

Saint Leonard
Located in St. Leonard, this vacation home is on the waterfront, within a 15-minute drive of Battle Creek Cypress Swamp Sanctuary and Perigeaux Vineyards and ...
WATERFRONT!!! The River's Roost on The Patuxent River
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 7.7 mi (12.4 km) from Spocott Windmill and 14 mi (22.5 km) from Richardson Maritime ...
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Riverside House w/ Kayaks, Piano & Fireplace

Riverside House w/ Kayaks, Piano & Fireplace

California
Located in California, this vacation home is by the ocean, within a 5-minute drive of Patuxent River and Drum Point Lighthouse.
Riverside House w/ Kayaks, Piano & Fireplace
Blue Heron Retreat on the Water

Blue Heron Retreat on the Water

Solomons
This family-friendly vacation home is 1.3 mi (2.2 km) from Annmarie Sculpture Garden and Arts Center and 1.8 mi (2.9 km) from Drum Point Lighthouse.
Blue Heron Retreat on the Water
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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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$102
Highest Price
AU$793
Popular accommodation
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC, Beautiful Waterfront Retreat in Cambridge!, Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND, WATERFRONT!!! The River's Roost on The Patuxent River, Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, Riverside House w/ Kayaks, Piano & Fireplace, Blue Heron Retreat on the Water, Beautiful Peaceful Home

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$368 per night from 5 Dec to 6 Dec
AU$368
includes taxes & fees
5 Dec - 6 Dec
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
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$158 per night from 1 Dec to 2 Dec
AU$158
includes taxes & fees
1 Dec - 2 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
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$229 per night from 5 Dec to 6 Dec
AU$229
includes taxes & fees
5 Dec - 6 Dec
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
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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$102 per night from 24 Nov to 25 Nov
AU$102
includes taxes & fees
24 Nov - 25 Nov
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 Dorchester County ...
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.