Taylors Island Vacation Rentals

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Vacation Rentals in Taylors Island

Waterfront Taylor’s Island Rental w/ Private Dock!
10.0 out of 10, Exceptional, (6)
"This was a great spot to come and visit. The dock gave the ability to crab and fish whenever. The house and view of the water were amazing. The only downfall for us was the amount of jelly fish so we did not get in the water much. We did bring our boat and launched it right down the road. We are out at the local restaurants and the community was welcoming. We drove around and saw the Harriet Tubman Underground Railroad and visited Cambridge many times."
Waterfront Taylor’s Island Rental w/ Private Dock!
Soul Oasis - home on the Chesapeake Bay
10.0 out of 10, Exceptional, (8)
"we really, really like the retro look and really enjoyed the space. It was quiet and we were able to relax."
The price is CA $178
CA $392 total
includes taxes & fees
Jul 23 - Jul 24
Soul Oasis - home on the Chesapeake Bay
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.8 out of 10, Exceptional, (6)
"We had a great time. Children and their parents spent a lot of time in the surprisingly large pool. Some adults chose the hot tub and the most active members of our group were paddleboarding and kayaking in the river. Severl people went hiking at Blackwater, and a few of us just sat on the screened in porch."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
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Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (55)
"Very clean small cottage in a beautiful spot. I was able to swim off the dock. There was plenty of outdoor space with comfortable Adirondack chairs. Very quiet at night and the beds were comfortable. Our host was most kind."
Waterfront Cottage in Beautiful Hoopers Island
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (4)
"Had a great time fishing from the dock while we got out of the city for a weekend."
Maryland Vacation Rental w/ Private Pool & Dock
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (7)
"Our family spent 10 fun filled days at Waterside Cottage. The house was spotless and had everything you could want or need.The kids enjoyed fishing and crabbing off the dock. Many hours were spent in the pool. Thank you Topher for a wonderful trip!"
Eastern Shore Waterside Cottage Near St. Michaels
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
9.2 out of 10, Wonderful, (11)
"It was honestly a perfect trip. The house was the perfect size and the back yard that went right to the edge of Lake Charming was amazing. The house was clean and many essentials were provided for us. Water pressure for showers was amazing, location was close enough to shops to have all our needs, short drive to Calvert Cliffs and Solomon’s Island. It’s a perfect location to relax and enjoy the scenery, good food, and go out to experience nature whether it’s right in the back yard or a short...
Lakefront Maryland Cabin w/ Fire Pit, Grill & Deck
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
10.0 out of 10, Exceptional, (1)
"Property and location couldn't be better! Host was very accommodating and quick to respond. Will definitely go back!"
The price is CA $301
CA $610 total
includes taxes & fees
Jul 8 - Jul 9
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (18)
"This house is incredible! Probably the cleanest rental house I have ever stayed in! The house was well stocked and very comfortable. However, we didn’t spend much time in the house because the outside is the real winner! The Crab House has everything to entertain kids and adults for hours! We spent all day in the yard, taking in the beautiful sights! If you are an early riser, like myself and one son, don’t miss the sunrise. So peaceful! If you are looking for crabs while there, Soft & Salty...
The price is CA $437
CA $778 total
includes taxes & fees
Jul 21 - Jul 22
Beautiful Waterfront Retreat in Cambridge!
The Schultz Estate
9.8 out of 10, Exceptional, (6)
"This property was great for our extended family of 8 and could have comfortably accommodated more. The old charm of the house was enjoyed by all. Great kitchen, functioning bbq, large dining room table and a fire pit for us all to enjoy. The sunset was beautiful as we sat outside in the evening. Wifi is available but it is limited so some online activities may not always be possible - but not a bad thing when you are spending time with family."
The Schultz Estate
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
9.6 out of 10, Exceptional, (4)
"Nice place for a getaway."
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (31)
"I liked everything about the house and got to see the wild life out side"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (41)
"This property was terrific for my husband, dog and me. It is well-maintained, clean, nicely decorated, and had everything we needed to make this a wonderful stay. The house is located within walking distance to everything North Beach has to offer. Thank you Danielle for being a great host."
The Blue Crab Beach House - Free beach passes
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (62)
"The house is a perfect retreat! I watched the sunrise from my bedroom and porch with my coffee each day of our stay. My parents live just 2 doors down. I have been coming to this neighborhood since the 70's. I still love hunting for fossils on the beach. Thank you for allowing us to book this spot!"
Mid-Century Modern and Marvelous on the Bay
Welcome to Hickory House on the Chesapeake Bay!
9.6 out of 10, Exceptional, (19)
"Had a great week! Cottage is adorable, clean and cozy. Host very welcoming with treats and bowls for our dogs. House is a couple weeks from the beach and a beach parking pass is included. The beach is private and very relaxing. It was very hot that week that we visited abd tge AC was excellent. Lots of extras in the house - games, hand soaps and even ballth salts! Very enjoyable visit!"
Welcome to Hickory House on the Chesapeake Bay!
Waterfront, Pool, Dock, Hot Tub.Stunning Views! A Luxury VIP Vacation Rental
9.4 out of 10, Exceptional, (16)
"We rented the house for the weekend to celebrate my mom’s 90th birthday! The house was amazing. Such a beautiful property. The pool was lovely and the view is spectacular. We were able to spend a peaceful weekend together, hanging out at the pool, looking at old photos and telling stories about my mom. The house is beautiful and it was like staying in a museum. So fascinating. The kitchen was well stocked, the porch is wonderful, and the rooms gave us enough space to spread out. Thank you for...
Waterfront, Pool, Dock, Hot Tub.Stunning Views! A Luxury VIP Vacation Rental
St. Michaels Waterfront Home
10.0 out of 10, Exceptional, (20)
"Beautiful house, perfect for a weekend getaway with young kids. The host was very helpful!"
St. Michaels Waterfront Home
Family Beach House: Spacious Deck, Grill & Views
10.0 out of 10, Exceptional, (1)
"The house was clean and quiet. The hosts were helpful and available for communication. This is a lovely house for a vacation away from crowds and by the beach."
The price is CA $325
CA $779 total
includes taxes & fees
Jul 1 - Jul 2
Family Beach House: Spacious Deck, Grill & Views
Historic Hoopersville Getaway on Chesapeake Bay!
9.6 out of 10, Exceptional, (9)
"Our vacation on Chesapeake Bay was wonderful. The house was clean and comfortable. It is an older home, but we loved the character and charm. There is a very large yard for playing, bikes and some board games/puzzles that we enjoyed. The island was very quiet so made for a relaxing vacation. The home came with kayaks, and we had a blast kayaking with our 2 and 4 year old on the ocean. I would highly recommend this home for a big gathering or small family like our trip. We felt so rested after...
Historic Hoopersville Getaway on Chesapeake Bay!
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (26)
"A well taken care of property. House was comfortable for the three of us. Almost a dozen fresh eggs during our time there. Firepit, dock, kayak and canoe, crab traps. Bald eagles, ospreys, great blue herons. A great place to trr wet jac or be active."
Waterfront Getaway with Dock
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See all available properties in Taylors Island
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.

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

Hyatt Regency Chesapeake Bay
4.0 star property
8.8 out of 10, Excellent, (1001)
"Nothing everything was great "
The price is CA $220
CA $307 total
includes taxes & fees
Jul 21 - Jul 22
Hyatt Regency Chesapeake Bay
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
2.5 star property
7.6 out of 10, Good, (1003)
"The property met my needs as I was only staying for one night, but the room seemed to be very humid which made it uncomfortable at times throughout the night. "
The price is CA $138
CA $153 total
includes taxes & fees
Jul 11 - Jul 12
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
Rod 'N' Reel Resort
3.0 star property
8.2 out of 10, Very good, (1002)
"Comfortable night stay rooms could be more updated and had musty smell "
The price is CA $299
CA $359 total
includes taxes & fees
Jun 30 - Jul 1
Rod 'N' Reel Resort
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.

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 CA $178 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. 

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.

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 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 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.

Recent reviews of Taylors Island properties
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