Search Cottages in Taylors Island

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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 62 Cottages in Taylors Island with updated reviews, rates, and availability.

Soul Oasis - home on the Chesapeake Bay
Sun loungers, beach towels

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (24)
"Perfect family get away with a great view!"
The price is AED 511
AED 1,094 total
includes taxes & fees
18 May - 19 May
Soul Oasis - home on the Chesapeake Bay
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.

9.2 out of 10, Wonderful, (20)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.
Waterfront Cottage in Beautiful Hoopers Island
Property grounds

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (70)
"This is a small, sweet, comfortable cottage, and was just perfect for our brief getaway from the hurly-burly. The house is very well equipped, especially the kitchen, so cooking the local seafood was easy. The decor (loved the faux fireplace) was charming and welcoming, down to the live Poinsettia plant on the table when we got there. "
Waterfront Cottage in Beautiful Hoopers Island
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (246)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier
Eastern Shore Waterside Cottage Near St. Michaels
Outdoor dining

Eastern Shore Waterside Cottage Near St. Michaels

10.0 out of 10, Exceptional, (19)
"Really enjoyed our stay, pool was nice and had plenty of amenities. We will definitely be coming back for another stay."
Eastern Shore Waterside Cottage Near St. Michaels
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Beach nearby

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

10.0 out of 10, Exceptional, (14)
"We had a very nice time at this house. The neighborhood was very nice to walk in and we enjoyed watching the Bay."
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
North Beach Cottage - Walk to Chesapeake Bay
Interior

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (32)
"The place was wonderful, clean and well stocked. It was a great place to stay - kudos to the hosts for an inviting atmosphere."
North Beach Cottage - Walk to Chesapeake Bay
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Property grounds

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

10.0 out of 10, Exceptional, (3)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
Beach towels

Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

10.0 out of 10, Exceptional, (88)
"Beautiful property in a great location!"
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣
Miscellaneous

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣

10.0 out of 10, Exceptional, (48)
"The views of the bay are magnificent, sunrise and sunset. The property is spotless. Toby and Kim, the hosts, could not be more accommodating. "
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣
Private waterfront cottage with pool on Church Creek
Fridge, microwave, oven, stovetop

Private waterfront cottage with pool on Church Creek

10.0 out of 10, Exceptional, (61)
Private waterfront cottage with pool on Church Creek
Waterfront, cozy cottage with private pool on 27 acres
Beach nearby

Waterfront, cozy cottage with private pool on 27 acres

9.8 out of 10, Exceptional, (87)
"Great property and the owners were gracious hosts."
Waterfront, cozy cottage with private pool on 27 acres
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Miscellaneous

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

10.0 out of 10, Exceptional, (8)
"Great little stay while taking part in the St. Michaels running events. Outstanding host."
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Charming Waterfront Cottage Retreat near St. Michaels
Fridge, microwave, oven, stovetop

Charming Waterfront Cottage Retreat near St. Michaels

10.0 out of 10, Exceptional, (4)
"Great weekend get away if you’re just looking for some peace and quiet with some great scenery. The kitchen was immaculate and everything was as listed."
Charming Waterfront Cottage Retreat near St. Michaels
Cottage at Goose Neck Point
Sun loungers, beach towels

Cottage at Goose Neck Point

10.0 out of 10, Exceptional, (32)
"Quite and enjoyable with easy access to a multitude of fabulous restaurants, and outdoor fun. "
Cottage at Goose Neck Point
Cottage Located on the Patuxent River!
Sun loungers

Cottage Located on the Patuxent River!

10.0 out of 10, Exceptional, (38)
"The accommodations were superb and being on the water was amazing!"
The price is AED 1,194
AED 1,441 total
includes taxes & fees
13 May - 14 May
Cottage Located on the Patuxent River!
Waterfront property with private boat ramp and new dock!
Outdoor dining

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

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)
Cottage on the Bay
Sun loungers, beach towels

Cottage on the Bay

6.0 out of 10, (1)
"This property has some good qualities. For one, it is right on the water, and you have access to three small beaches and good fishing. It was nice to wake up and drink coffee next to the waves. The house was stocked and seemed to have everything we could’ve needed. However, for us, the negatives far outweighed the positives here. Most significantly to me, the property did not mention that the outdoor amenities - the fire pit, grills, and boats - are shared between you and the adjoining property....
Cottage on the Bay
The Middle Point Cabin in Saint Michaels
Fridge, microwave, oven, stovetop

The Middle Point Cabin in Saint Michaels

9.8 out of 10, Exceptional, (48)
"Cute place. Good location, 15 mins from St Michael’s. We were quite happy."
The Middle Point Cabin in Saint Michaels
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

Soul Oasis - home on the Chesapeake Bay
Sun loungers, beach towels

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (24)
"Perfect family get away with a great view!"
The price is AED 511
AED 1,094 total
includes taxes & fees
18 May - 19 May
Soul Oasis - home on the Chesapeake Bay
The Blue Crab Beach House - Free beach passes
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (54)
"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 Lazy Crab Beach House - Free beach passes
Property grounds

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (48)
"Would stay again."
The Lazy 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.