Taylors Island Holiday Rentals

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Holiday Rentals in Taylors Island

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (256)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
Family and Pet-Friendly, Waterfront with Pier

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (179)
"Cottage was just as pictured. Lots of character and charm. Host, Brett was easy to work with and very helpful!"
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

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

9.8 out of 10, Exceptional, (7)
"Great House "
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (13)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is AU$589
includes taxes & fees
7 Oct - 8 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

10.0 out of 10, Exceptional, (26)
"Wow, what a homerun of a vacation house - it had everything we needed and more. We had the best time and hope to be back soon."
RANCH AT ROYAL OAK- Exclusive waterfront pool pier

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.8 out of 10, Exceptional, (13)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (10)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (77)
"We had a very nice stay and enjoyed the quiet environment and the amenities of the property. Lots of great area for walking. "
Waterfront Cottage in Beautiful Hoopers Island

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

9.6 out of 10, Exceptional, (8)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
The Cozy Crab- Your Charming Haven in Lovely North Beach!

"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Clean, well-appointed kitchen. Loved the crab shack!! Would highly recommend. Used the kayaks and canoe. The pool was perfect! The property is beautiful. Highly reccomend"
"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!

Single family home with screened porch.

10.0 out of 10, Exceptional, (12)
"The house was very nicely done and extremely well stocked and the host was very friendly and super easy to deal with. We especially like the location for sunrise walks with the dogs and easy access to the national parks. "
Single family home with screened porch.

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

9.8 out of 10, Exceptional, (132)
"Beautiful property with gorgeous view. The owner was helpful and accommodating. Everything was clean and the amenities were superb. An evening of kayaking on the water was amazing. Great location for the half Ironman as well! "
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Solomons Apartment

9.2 out of 10, Wonderful, (12)
"Very clean, awesome location and amazing hosts!! "
The price is AU$468
includes taxes & fees
8 Oct - 9 Oct
Waterfront Solomons Apartment

Thorneton Point Estate

9.6 out of 10, Exceptional, (20)
"Beautiful, well-maintained property in a gorgeous waterside setting. "
Thorneton Point Estate

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

10.0 out of 10, Exceptional, (54)
"Such a beautiful place to stay. Had absolutely everything you could need. Comfy beds and tons of space. Definitely recommend staying here!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Belle of the Chesapeake Bay

9.0 out of 10, Wonderful, (14)
"This was a great place to stay in a quiet neighborhood, a short drive from Calvert Cliffs State Park. Plenty of space for four adults. We could have stayed longer and would not hesitate to book again."
Belle of the Chesapeake Bay

Waterfront property with private boat ramp and new dock!

9.6 out of 10, Exceptional, (14)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!

Heated pool, sandy beach, pier, and playground set punch point apart!

10.0 out of 10, Exceptional, (10)
"Beautifully decorated, peaceful, well appointed home for our girls bday celebration. Highly recommend."
Heated pool, sandy beach, pier, and playground set punch point apart!

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

10.0 out of 10, Exceptional, (14)
"Gorgeous views and location. "
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

9.8 out of 10, Exceptional, (74)
"We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
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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Top Taylors Island Hotel Reviews

Find out more about Taylors Island

Find out more about Taylors Island

Everything you need to know about Taylors Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Taylors Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Taylors Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Taylors Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Taylors Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Taylors Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Taylors Island holiday rentals we have selected for you start as low as AU$468 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Taylors Island rentals

At Expedia, we put the best Taylors Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Taylors Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Taylors Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Taylors Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Taylors Island?

Yes, there are holiday rentals close to the most popular sights in Taylors Island, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Taylors Island has to offer?

The Cozy Crab- Your Charming Haven in Lovely North Beach!: This holiday home rental outside of Taylors Island offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of books.

How many holiday rentals will I find in Taylors Island?

Expedia has 4 holiday rentals for your stay in Taylors Island.

What’s there to see and do in Taylors Island?

While exploring the area, visit family-friendly sights like Richardson Maritime Museum, or get outside and enjoy nature at Blackwater National Wildlife Refuge. Cove Point Lighthouse and Harriet Tubman Underground Railroad National Historical Park are a couple of places you'll find in the wider area.

What’s a holiday rental in Taylors Island like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Taylors Island. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family trips or small group gatherings.