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Compare 202 Vacation Homes in Taylors Island with updated reviews, rates, and availability.

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

9.6 out of 10, Exceptional, (29)
"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!

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

Beautiful Peaceful Home

10.0 out of 10, Exceptional, (2)
"I was deciding between booking a hotel or a home and thankful that we decided on this home for our weekend getaway. After visiting the museums in Cambridge, we were welcomed to our home away from home. Very relaxing, comfortable and spacious for our family. Conveniently located to downtown and nice neighborhood. If looking for a home to stay when in the Cambridge area, this is an excellent choice."
Beautiful Peaceful Home

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (47)
"Everything close by!"
The Blue Crab Beach House - Free beach passes

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

9.6 out of 10, Exceptional, (19)
" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

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

9.8 out of 10, Exceptional, (110)
"Very nice place we found, great views, very clean, quiet, great place to relax for the weekend. everything went well and we would highly recommend anyone for a stay here. we will be back next year"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (40)
"My family of five and our pup just had a wonderful Thanksgiving break staying at the lazy crab. The home was very clean, equipped with just the right amount of things to make our stay easy without cluttering the space. The beds were comfortable, the fenced in yard was perfect for our four-legged family member, and we enjoyed being able to walk to restaurants and to the beach. Everyone we encountered was kind and welcoming in town, and we had fun digging for shark teeth with our kids too. Even in...
The Lazy Crab Beach House - Free beach passes

The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!

9.4 out of 10, Exceptional, (42)
"We stayed for the weekend to attend a wedding nearby. The size of the home was perfect for our family of 5. It was clean and well equipped. We enjoyed morning coffee on the deck! The only issue was that one of the queen beds was really hard and not very comfortable. "
The Normandy Cottage ~ Charming Getaway ~ On The Shores Of The Chesapeake!

Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

9.8 out of 10, Exceptional, (19)
"The house was very comfortable and well stocked! It has everything you need for a relaxing time. "
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC

10.0 out of 10, Exceptional, (10)
"Great place to stay while in the area. Thank you!"
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC

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

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!

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

The Blackwater refuge country house on a quiet 12 acres

9.8 out of 10, Exceptional, (9)
"Listing and photos accurately describe accommodations. We were comfortable and satisfied. A nice rural location for perusing outdoor activities - fishing, hunting, boating, paddling, birdwatching. Good parking for a boat trailer. "
The Blackwater refuge country house on a quiet 12 acres

Riverside House w/ Kayaks, Piano & Fireplace

9.0 out of 10, Wonderful, (12)
"This house is well-maintained and my business associates enjoy staying here. We will book this house every time it comes available."
Riverside House w/ Kayaks, Piano & Fireplace

Bayfront Gem w/ Amazing Water Views + Pond!

10.0 out of 10, Exceptional, (12)
"Wonderful house with great views of water. Everything was as advertised and we had a very relaxing stay. Will definitely consider returning. "
Bayfront Gem w/ Amazing Water Views + Pond!

Cottage on the Bay

9.8 out of 10, Exceptional, (6)
"Clean and accommodating host. Has many of the necessities for the home, including washer/dryer , soaps , trash bags , cleaning essentials , plates/bowls/cups, kitchen gadgets , and more. Home feels safe away from predator animals . Couple deers around. Bring insect repellent."
Cottage on the Bay

Beautiful Beach Boutique 2 Beaches, 1 lake, mature trees for beauty and privacy

9.4 out of 10, Exceptional, (3)
"We were in town for a reunion and this was a nice alternative to the local hotels. Updates to the house were nicely done and I love that checkout was simplified to two to three tasks, not a whole laundry list. If I had two suggestions, one would be that the plug-ins were too many and too strong - we considered opening a window for some relief but did not since we were out at the reunion most of the day. But only one per floor would likely be enough although the house is so clean (five stars!)...
Beautiful Beach Boutique 2 Beaches, 1 lake, mature trees for beauty and privacy

3 Bedrooms Relaxing Rustic House on Saint Thomas CreeK

3 Bedrooms Relaxing Rustic House on Saint Thomas CreeK

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
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

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

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (40)
"My family of five and our pup just had a wonderful Thanksgiving break staying at the lazy crab. The home was very clean, equipped with just the right amount of things to make our stay easy without cluttering the space. The beds were comfortable, the fenced in yard was perfect for our four-legged family member, and we enjoyed being able to walk to restaurants and to the beach. Everyone we encountered was kind and welcoming in town, and we had fun digging for shark teeth with our kids too. Even in...
The Lazy Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (47)
"Everything close by!"
The Blue Crab Beach House - Free beach passes
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.