Taylors Island Vacation Rentals

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Check prices for these dates

In two weeks
Oct 31 - Nov 2
In one month
Nov 14 - Nov 16
In two months
Dec 12 - Dec 14
In three months
Jan 9 - Jan 11

Vacation Rentals in Taylors Island

The Cozy Crab- Your Charming Haven in Lovely North Beach!
Outdoor dining
The Cozy Crab- Your Charming Haven in Lovely North Beach!
9.6 out of 10, Exceptional, (10)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Dining
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
10.0 out of 10, Exceptional, (180)
"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
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
9.6 out of 10, Exceptional, (16)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is ￥25,702
￥56,892 total
includes taxes & fees
Oct 20 - Oct 21
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior detail
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, (12)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cozy Cottage with access to and partially obstructed views of the bay.
Fridge, microwave, oven, stovetop
Cozy Cottage with access to and partially obstructed views of the bay.
9.0 out of 10, Wonderful, (30)
"Property was cozy and clean. Owners left lights on for us knowing we had a late arrival. Would definitely stay again. "
Cozy Cottage with access to and partially obstructed views of the bay.
Waterfront Wildlife Retreat on the Patuxent River
Interior
Waterfront Wildlife Retreat on the Patuxent River
10.0 out of 10, Exceptional, (171)
"We went here just for a little weekend getaway for my boyfriend, his brother, his brother’s girlfriend and their kids. We had the absolute best time, such a nice getaway even if it was only for 3 days. The view of the bay from the house is gorgeous and everything was perfect. I will be recommending this stay to anyone I can! "
Waterfront Wildlife Retreat on the Patuxent River
Family and Pet-Friendly, Waterfront with Pier
Exterior
Family and Pet-Friendly, Waterfront with Pier
10.0 out of 10, Exceptional, (259)
"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
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Smart TV, fireplace
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
10.0 out of 10, Exceptional, (58)
"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
Waterfront Solomons Apartment
Interior
Waterfront Solomons Apartment
9.2 out of 10, Wonderful, (12)
"Very clean, awesome location and amazing hosts!! "
The price is ￥20,411
￥40,707 total
includes taxes & fees
Oct 14 - Oct 15
Waterfront Solomons Apartment
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Outdoor pool, a heated pool
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
Waterfront Cottage in Beautiful Hoopers Island
Property grounds
Waterfront Cottage in Beautiful Hoopers Island
10.0 out of 10, Exceptional, (80)
"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
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Marina
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
8.8 out of 10, Excellent, (5)
"The place was very clean and in the most perfect spot in downtown Cambridge. We had a wedding walking distance from this place. Jen is a very responsive and accommodating host!"
The price is ￥16,631
￥43,110 total
includes taxes & fees
Oct 14 - Oct 15
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
The Blue Crab Beach House - Free beach passes
Beach nearby, sun loungers, beach towels
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (72)
"The cleanliness, coziness, and convenience was great — exactly as described on the website. We would definitely recommend this VRBO to whoever was looking for a place in North Beach! "
The Blue Crab Beach House - Free beach passes
Sweet Bamboo Beach Cottage
Fridge, microwave, oven, stovetop
Sweet Bamboo Beach Cottage
9.8 out of 10, Exceptional, (80)
"Cute and clean house..close to beach and restaurants!! We will visit again !"
Sweet Bamboo Beach Cottage
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Private beach
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
10.0 out of 10, Exceptional, (16)
"Gorgeous views and location. "
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Belle of the Chesapeake Bay
Beach
Belle of the Chesapeake Bay
9.2 out of 10, Wonderful, (16)
"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 Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Terrace/patio
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
9.8 out of 10, Exceptional, (132)
"I booked this house for the property, the backyard, the dock, and it didn't disappoint. It's also about 20 mins from the main town (Cambridge) which was exactly what we wanted - a break from crowds and the bustle. We had such a relaxing few days just reading, fishing from the dock, and kayaking. We were four people, but this would easily fit two families. A wonderful stay overall."
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Sun loungers, beach towels
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
10.0 out of 10, Exceptional, (36)
"This is a beautiful property, well appointed, but not too formal for families wanting to be in the pool or on the water all day. We were a party of 12 including six grandchildren. There was plenty to do for the adults and the grandchildren and plenty of space in the home to not feel like you were on top of each other. The sunsets were spectacular. Marissa is an extremely responsive host, and all our questions were answered in a timely fashion. Saint Michaels is very close by and an absolutely...
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Property grounds
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
10.0 out of 10, Exceptional, (49)
"The house was exactly how the pictures showed !Cute and cozy ,and clean ! Im a country girl and felt at home sitting on the porch,enjoying the breeze. The sound of the ocean was a bonus!! Quiet and peaceful. I enjoyed the beautiful sunrises and morning walk on the dock. Overall i enjoyed my stay appreciate the hospitality of the host and would booked again !! "
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
Fridge, microwave, oven, stovetop
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
10.0 out of 10, Exceptional, (90)
"This property is even prettier in person!! We have a huge extended family and there was plenty of space for everyone. The host and property manager both made themselves available to answer any questions and responded very quickly. Excellent trip - we would love to stay again in the future!"
Luxurious and Extremely Private Waterfront Estate (SORRY - NO WEDDINGS)
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

Comfort Inn & Suites

Comfort Inn & Suites

10/10 Excellent
"everything was great"
Brent S 2-night trip
Posted 19 hours ago
Comfort Inn & Suites

Find out more about Taylors Island

Search for holiday rentals in Taylors Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Taylors Island using one of the methods below:

  • View our selection of featured holiday rentals in Taylors Island
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Look no further and take a look at our great range of rental properties in Taylors Island!

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?

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock: You might like this vacation home rental near Taylors Island. It is located on the beach and has an outdoor pool, a fireplace, 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. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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.