Taylors Island Vacation Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

This weekend
Next weekend

Vacation Rentals in Taylors Island

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

9.4 out of 10, Exceptional, (18)
"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."
Cozy Cottage with access to and partially obstructed views of the bay.

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (49)
"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 !"
The Blue Crab Beach House - Free beach passes

Sweet Bamboo Beach Cottage

9.8 out of 10, Exceptional, (70)
"Couldn’t be happier with our stay. The house was exactly as pictured. Neighborhood was quiet with a small town feel. Most of the major appliances appeared relatively new, the beds were comfortable and the house was staffed with an abundance of linens and towels. Front and back yards are completely fenced in which is perfect for those with small dogs. North Beach is only a short drive from College Park, Baltimore and Annapolis. Check in was a breeze. Would definitely consider staying there...
Sweet Bamboo Beach Cottage

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (43)
"Would stay again."
The Lazy Crab Beach House - Free beach passes

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

10.0 out of 10, Exceptional, (172)
"We were looking for a quiet stay in a beautiful place and that was our experience. The view of the bay is spectacular. The neighborhood is quiet and an easy drive from DC, so this is a great place to find some peace when that's what's needed. There was a windstorm that knocked out power for much of the region one day. Brett was responsive and helpful in dealing with that unexpected event. "
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (19)
"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!"
The price is CA $201
CA $422 total
includes taxes & fees
Mar 16 - Mar 17
Soul Oasis - home on the Chesapeake Bay

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

9.6 out of 10, Exceptional, (21)
"Very large nicely appointed house with lots of space for large groups. Unfortunately the pool heater was out of service but they gave us a rebate for the inconvenience. One major deficiency is the internet/WIFI with is satellite and somewhat slow and dropped frequently . If you need streaming for work or other activities you might be frustrated."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

9.8 out of 10, Exceptional, (40)
"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...
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (158)
"Clean and nice location. Worked perfectly for our visit to the area to spend time with our daughter, son-in-law, and two perfect grandsons. Thank you for sharing your beautiful home and location. "
Waterfront Wildlife Retreat on the Patuxent River

Belle of the Chesapeake Bay

9.2 out of 10, Wonderful, (12)
"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...
Belle of the Chesapeake Bay

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (38)
"Stayed at the rental for a day sandwiched between two nights. Perfect for R&R. "
The price is CA $333
CA $402 total
includes taxes & fees
Mar 7 - Mar 8
Waterfront Getaway with Dock

4-BR Waterfront Turret Home

2.0 star property
10.0 out of 10, Exceptional, (1)
"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!!"
The price is CA $434
CA $990 total
includes taxes & fees
Mar 26 - Mar 27
4-BR Waterfront Turret Home

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

10.0 out of 10, Exceptional, (76)
"Panoramic views of the water and sunsets. Loved the elevation of the property and the gorgeous trees that framed but did not obstruct the view. The layout was great and attention to detail throughout the home impressive."
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (242)
"If you’re looking for a remote location on the water, this is it. House was clean, hosts were nice. No complaints. "
Family and Pet-Friendly, Waterfront with Pier

The Schultz Estate

8.4 out of 10, Very good, (15)
"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!"
The Schultz Estate

Eastern Shore Waterside Cottage Near St. Michaels

10.0 out of 10, Exceptional, (19)
"Had a great visit. House was perfect and the area is absolutely gorgeous"
Eastern Shore Waterside Cottage Near St. Michaels

Maryland Vacation Rental w/ Private Pool & Dock

10.0 out of 10, Exceptional, (6)
"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. "
Maryland Vacation Rental w/ Private Pool & Dock

Luxury Waterfront Retreat with in ground pool and close to town

10.0 out of 10, Exceptional, (34)
"12 of my friends and i stayed here for my birthday, not only did the hosts leave me a nice birthday gift, but a wonderful place to hang out for a weekend. The place is immaculate and well thought out. They paid attention to every detail! The kitchen is fully stocked so that we could cook for and feed all 13 of us. The entire weekend people kept telling me it was so comfortable, so clean, surprisingly well stocked, beautiful, fun to be in, etc.! Will definitely return! Mindy was very responsive...
Luxury Waterfront Retreat with in ground pool and close to town

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2.0 star property
9.6 out of 10, Exceptional, (4)
"Very clean, well stocked with towels, paper products and everything else you need. Lots of space for a large group. I liked the master bedroom on the first floor. Having a second coffee maker upstairs is a nice touch. Walking distance to downtown. "
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

10.0 out of 10, Exceptional, (7)
"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."
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
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.
Don't see what you're looking for?
See all available properties in Taylors Island
Save an average of 15% on thousands of hotels when you're signed in

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)
"Love staying here. The hot tub is great, love the common areas. "
The price is CA $288
CA $396 total
includes taxes & fees
Mar 11 - Mar 12
Hyatt Regency Chesapeake Bay

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

2.5 star property
7.6 out of 10, Good, (1002)
"Very nice and helpful front desk staff. Room was great. Very clean, nice and spacious. Breakfast was good. I made a perfect choice for my stay."
The price is CA $134
CA $149 total
includes taxes & fees
Mar 9 - Mar 10
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

Rod 'N' Reel Resort

4.0 star property
8.2 out of 10, Very good, (1004)
"Loved my Stay"
The price is CA $168
CA $215 total
includes taxes & fees
Mar 25 - Mar 26
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.

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?

The Lazy Crab Beach House - Free beach passes : This vacation home rental near Taylors Island is located in the city center and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.