Taylors Island Vacation Rentals : Short-Term Rentals for 2025

Q: What are some of the best vacation rentals in Taylors Island?

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock! : Located near Taylors Island, this vacation home rental is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a spa tub.

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Vacation Rentals in Taylors Island

"My wife and I stayed two nights to visit family. Cottage was as described, very roomy and comfortable. Great location. Host was very kind. Only dislike was smell from oil heat, I've never had oil heat and not sure if that is normal."

"Beautiful place, very clean and nicely decorated. The only thing I wish was better was to have a bathroom upstairs and the stairs to be a bit easier to access, they are a bit tricky for those over 50:) nice view too!"

CA $415 total

includes taxes & fees

Feb 3 - Feb 4

"The house was just as it was listed!! Our annual family vacation was so much fun here! Plenty of room, very clean, and fully stocked! Peddle boats, kayaks, and pool used daily!! Fire every night!!! Thank you for the wonderful hospitality!!!"

"Terrific house, beautiful scenery, property management was very responsive and helpful. Would stay again. Thank you. "

"We really enjoyed our stay at The Blue Crab Beach House. The home was very clean and well accessorized. The host was very responsive and I would definitely come stay again !"

"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."

"Would stay again. Steps down to the water are a challenge"

"This property is a phenomenal place to spend time with family and enjoy beautiful St. Michael’s. The house is well stocked and convenient to town. We’d love to come back. "

"We needed a house for a quick stay in Lusby. The hosts have thought of everything to make the stay easy. They communicated ahead of our trip and were easy to work with. "

"Our granddaughters live in the neighborhood and our youngest was having her first birthday! It was just my husband and myself, way more house than we needed but tons more comfortable than a hotel. The winter views of the Bay from the living room were awesome. I highly recommend you make a cup of coffee and watch the sunrise. A few surprises with the house itself, the most egregious for me was the fireplace pictured is not functional. The hosts have done a nice job with this house and are still...

"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"

CA $737 total

includes taxes & fees

Feb 3 - Feb 4

"Location was perfect for what we needed (quiet, on the beach, great views). Family & pup will definitely be back! We wished we could have stayed longer. Owner communication was wonderful, we never needed anything but knew we could reach out if we did. Very comfortable experience throughout. "

"This house was just what we needed for our business associates. "

"We truly loved our stay! The home was super comfortable and well stocked for making Thanksgiving dinner for 6. We loved just looking out at the geese, swans and blue herons ! Really lovely. We’ll be back!"

"Would stay again."

"Perfect large space on a quiet and pretty area. Really great space. "

"What a wonderful stay we had! The house was so comfortable with plenty of space for everyone to relax and enjoy each other's company. We enjoyed the brisk mornings on the porch and the gorgeous sunsets in the evenings. Very comfortable beds and linens. The scenery and landscape in the area are breathtaking. Every turn provided another incredible view of the water. Fishing Creek is close to so many beautiful, quaint towns along the Chesapeake Bay. Highly recommend!"

"Our group of longtime friends from different states wanted a convenient location to meet for a weekend getaway. The Eastern Shore was a good location and this property was a wonderful and comfortable place for our group. The house was spacious and had plenty of areas for members of the group to enjoy all together or in smaller conversation groups. Our group meals were easy to prepare in the large and well-equipped kitchen. The dining room easily accommodated our group for our dinners and the...

"We had a wonderful stay here. The house has a really functional kitchen so we were able to cook a lot of meals here. The pool was perfect for young swimmers (decent sized shallow end) and we loved hanging out on the dock, crabbing and kayaking. With plenty of adult bikes, we took a trip each morning to the playground too. We hope to be back!"

"Great house with an outstanding view. We enjoyed our stay and the communication with the management group was great. "

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Other types of properties in Taylors Island you may be interested in

Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers

"Great check in and highly personable staff. Dawn Reed and service staff with luggage transfer were excellent. Pool area looked amazing. Mitcherners service and bar food were provided great atmosphere and delicious food."

CA $329 total

includes taxes & fees

Feb 25 - Feb 26

"Nice "

CA $200 total

includes taxes & fees

Feb 17 - Feb 18

"What we love most is the family feel of all the employees making our stay feel more like a B&B rather than a hotel. Absolutely love the staff!"

CA $186 total

includes taxes & fees

Feb 16 - Feb 17

Find out more about Taylors Island

Everything you need to know about Taylors Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Taylors Island vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Taylors Island vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Taylors Island vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Taylors Island vacation rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Taylors Island rentals

At Expedia, we put the best Taylors Island vacation 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 vacation.

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.

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Frequently asked questions

Can I find vacation rentals in Taylors Island?

Yes, there are vacation rentals near the most popular local attractions in Taylors Island, or you can select a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Taylors Island?

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!: Located near Taylors Island, this vacation home rental is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a spa tub.

How many vacation rentals will I find in Taylors Island?

Expedia has 4 vacation 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 Ruark Boatworks, or get outside and enjoy nature at Blackwater National Wildlife Refuge. Cove Point Lighthouse and Cove Point Beach are a couple of places you'll find in the larger area.

What’s a vacation rental in Taylors Island like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Taylors Island. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a family getaway.

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Taylors Island Vacation Rentals

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Vacation Rentals in Taylors Island

Cozy Cottage with access to and partially obstructed views of the bay.

Soul Oasis - home on the Chesapeake Bay

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

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

Maryland Vacation Rental w/ Private Pool & Dock

Belle of the Chesapeake Bay

4-BR Unique Waterfront House - Your Perfect Escape

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

4BDRM River front house with Private Beach in Hollywood

Turn Winter Blues Into Blissful Views, Book Now!

The Lazy Crab Beach House - Free beach passes

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

The Schultz Estate

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

Breathtaking Waterfront Estate

Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou

Other types of properties in Taylors Island you may be interested in

Hyatt Regency Chesapeake Bay

Rod 'N' Reel Resort

Springhill Suites by Marriott Prince Frederick

Find out more about Taylors Island

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