Search Cottages in Taylors Island

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Compare 51 Cottages in Taylors Island with updated reviews, rates, and availability.

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

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

9.6 out of 10, Exceptional, (14)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Blue heron sunset

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

10.0 out of 10, Exceptional, (7)
"“Point of View” waterfront cottage did not disappoint. In fact, it was beyond expectations. Maria’s (the host) personal touches made the cottage feel like home. We used “Point of View” as overflow for a family reunion we were having. It is perfectly situated for easy walking to anything you need or want to do on Tilghman Island. The views from the cottage are amazing. Being on the entrance to Dogwood Harbor provides you with a real time experience of what a waterman’s life is truly all...
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Soul Oasis - home on the Chesapeake Bay
Exterior

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (18)
"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 SAR 484
SAR 1,083 total
includes taxes & fees
29 Dec - 30 Dec
Soul Oasis - home on the Chesapeake Bay
Waterfront Cottage in Beautiful Hoopers Island
Enjoy a beautiful sunrise from the back deck

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (65)
"My boyfriend and I needed to get away. This house and location was just what we needed. Beautiful scenery, cozy home. We started a full week and I was sad to go at the end of our trip. We look forward to visiting again in the future! "
Waterfront Cottage in Beautiful Hoopers Island
The Middle Point Cabin in Saint Michaels
Living area

The Middle Point Cabin in Saint Michaels

9.8 out of 10, Exceptional, (48)
"nice property. secluded. clean and comfortable. owners very very responsive. "
The Middle Point Cabin in Saint Michaels
Waterfront, cozy cottage with private pool on 27 acres
Private Pool

Waterfront, cozy cottage with private pool on 27 acres

9.8 out of 10, Exceptional, (87)
"We had a wonderful time overlooking the water and swimming in the refreshing pool while enjoying easy access to downtown Cambridge and Blackwater NW Refuge."
Waterfront, cozy cottage with private pool on 27 acres
Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣
Every sunrise brings new hope for a brighter future.

Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣

10.0 out of 10, Exceptional, (46)
"Great experience, wonderful cozy cottage with thoughtful touches throughout. Remote, peaceful location with excellent fishing and crabbing all around you. Fantastic eating at Old Salty's less than a couple of miles away. Very dog friendly cottage and lovely screened in porch area to sit and watch the sunsets. We will be booking again next year."
Off-season prices! Waterfront Cottage on Hoopers Island. Pet friendly. 🏝️🦀🎣
Eastern Shore Waterside Cottage Near St. Michaels
wrap around porch with rockers and dining area

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
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (2)
"Great little cottage, beautiful scenery, quiet and peaceful. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Waterfront property with private boat ramp and new dock!
Exterior

Waterfront property with private boat ramp and new dock!

9.6 out of 10, Exceptional, (8)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!
Cottage at Goose Neck Point
Living area

Cottage at Goose Neck Point

10.0 out of 10, Exceptional, (31)
"We loved everything about this sweet cottage on the water! The decor was top notch, and so welcoming! We stayed 3 nights, and can’t say enough about this beautiful area of Maryland. Great restaurants, shoppes, and delicious crabs! We also did the ferry ride over to Oxford. Had an amazing time at this property! The host also left some yummy treats, and a bottle of champagne for our anniversary! Can’t wait to come back!"
Cottage at Goose Neck Point
North Beach Cottage - Walk to Chesapeake Bay
North Beach Vacation Rental | 3BR | 2BA | 1,304 Sq Ft | Steps Required to Access

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (28)
"This little farmhouse is great. Updated and very clean with an unbelievable location just a short walk to the beach. "
North Beach Cottage - Walk to Chesapeake Bay
Cottage Located on the Patuxent River!
Room

Cottage Located on the Patuxent River!

10.0 out of 10, Exceptional, (38)
"The property and the cottage are just beautiful [very quiet] and incredibly well appointed. The bed is super cozy. There is no kitchen but the coffee station was great to have. Note that the cottage shares the property with the main house. My husband and I enjoyed sitting by the river multiple times during our stay and we really appreciated our hosts’ hospitality and communication. Thank you for the beautiful respite!"
The price is SAR 1,108
SAR 1,337 total
includes taxes & fees
8 Jan - 9 January 2025
Cottage Located on the Patuxent River!
Family-friendly Chesapeake Beach House With Deck!
Living area

Family-friendly Chesapeake Beach House With Deck!

3.0 star property
6.0 out of 10, (1)
Family-friendly Chesapeake Beach House With Deck!
Modern Solomons Cottage Rental - Walk to Island!
Solomons Vacation Rental | 1BR | 1BA | 525 Sq Ft | 3 Steps to Access

Modern Solomons Cottage Rental - Walk to Island!

10.0 out of 10, Exceptional, (9)
"This place was so cute and cozy. Fabulous!"
Modern Solomons Cottage Rental - Walk to Island!
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Exterior

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (2)
"Quiet, peaceful, relaxing!"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Terrace/patio

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

3.0 star property
10.0 out of 10, Exceptional, (1)
"It really is an adorable cottage, very tastefully decorated.the owner provided a very thoughtful gift basket on arrival. I would recommend this cottage to anyone."
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Outdoor dining

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

10.0 out of 10, Exceptional, (13)
"I cannot say enough positive things about my stay at Kelcey's adorable home. She has been the most thorough and considerate host "
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Exterior

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

3.0 star property
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Riverside House w/ Kayaks, Piano & Fireplace
Exterior

Riverside House w/ Kayaks, Piano & Fireplace

3.0 star property
Riverside House w/ Kayaks, Piano & Fireplace
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
Taylors Island Vacation Rental | 3BR | 2.5BA | 2,100 Sq Ft | 1-2 Steps Required

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
The Lazy Crab Beach House

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
The Blue Crab Beach House

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.

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