Search Vacation Homes in Taylors Island

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Check prices for these dates

Next weekend
14 Rab. I - 16 Rab. I
In two weeks
21 Rab. I - 23 Rab. I
In one month
4 Rab. II - 6 Rab. II
In two months
2 Jum. I - 4 Jum. I

Compare Vacation Homes in Taylors Island with updated reviews, rates, and availability.

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (19)
"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!!!"
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Fridge, microwave, oven, stovetop

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

9.4 out of 10, Exceptional, (30)
"This was our third year celebrating our family Thanksgiving in this home. Three generations coming from three different states. Location offers an easy drive for everyone, and the home is large enough for us spread out yet gather for meals. The host listened to our comments from previous years and addressed all of our concerns. Will be returning again."
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Interior

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
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Fridge, microwave, stovetop, dishwasher

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

9.6 out of 10, Exceptional, (21)
"Terrific house, beautiful scenery, property management was very responsive and helpful. Would stay again. Thank you. "
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
The Blue Crab Beach House - Free beach passes
Miscellaneous

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
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Interior

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
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Beach

Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

9.8 out of 10, Exceptional, (11)
"Would stay again. Steps down to the water are a challenge"
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock
Living area

Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

10.0 out of 10, Exceptional, (1)
"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. "
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock
Belle of the Chesapeake Bay
Beach

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
4-BR Waterfront Turret Home
Interior

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 SAR 1,125
SAR 2,568 total
includes taxes & fees
26 Mar - 27 Mar
4-BR Waterfront Turret Home
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
On the beach

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

10.0 out of 10, Exceptional, (112)
"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. "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
4BDRM River front house with Private Beach in Hollywood
Property grounds

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.6 out of 10, Exceptional, (5)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood
Serene Waterfront Minutes from St Michaels.
Terrace/patio

Serene Waterfront Minutes from St Michaels.

9.8 out of 10, Exceptional, (7)
"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!"
Serene Waterfront Minutes from St Michaels.
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!
Beach

2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!

10.0 out of 10, Exceptional, (2)
"Quite and friendly neighbors "
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!
Bay Views & Fire Pit: Taylor’s Island Retreat
Fridge, microwave, stovetop, dishwasher

Bay Views & Fire Pit: Taylor’s Island Retreat

10.0 out of 10, Exceptional, (11)
"The house had a beautiful view. It was well stocked. Management was very responsive. Enjoyed a nice Thanksgiving with beautiful sunsets. Very private. Loved every aspect."
Bay Views & Fire Pit: Taylor’s Island Retreat
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
Interior

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

10.0 out of 10, Exceptional, (24)
"The Ranch at Royal Oak was a fantastic property. The property was exactly as advertised - gorgeous waterfront estate with a large lawn. Incredibly peaceful. We were looking for a getaway to hit pause and just relax and the ranch Royal Oak was exactly what we needed. Marissa was a great host - incredibly responsive, check in instructions are very clear.and easy to follow. I highly recommend this property for your next getaway."
RANCH AT ROYAL OAK- Exclusive waterfront pool pier
NEW! Gorgeous Waterfront Estate with pool, beach and dock
Outdoor pool

NEW! Gorgeous Waterfront Estate with pool, beach and dock

9.6 out of 10, Exceptional, (5)
"Great House "
NEW! Gorgeous Waterfront Estate with pool, beach and dock
Downtown Oxford | Outdoor Dining | Character Filled
Smart TV, books

Downtown Oxford | Outdoor Dining | Character Filled

Downtown Oxford | Outdoor Dining | Character Filled
Heated pool, sandy beach, pier, and playground set punch point apart!
Miscellaneous

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

10.0 out of 10, Exceptional, (4)
"Everything about this property was perfect for our family of 10 ranging in age from 79 to 2.5. The children loved the indoor and outdoor play areas, and it was hard to drag them away from the house for Thanksgiving dinner. The location was excellent for access to St Michael's and other spots on the eastern shore. The owner even helped us find a place to get fresh local oysters and shucking them was a family affair."
Heated pool, sandy beach, pier, and playground set punch point apart!
Luxury Waterfront Retreat with in ground pool and close to town
Miscellaneous

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
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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Other property types in Taylors Island

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

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
Miscellaneous

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
Fridge, microwave, oven, stovetop

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
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.