Book Taylors Island Cottages
Wander Wisely with exceptional service, 24/7 support
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Featured Cottages in Taylors Island

Waterfront Cottage in Beautiful Hoopers Island

North Beach Cottage - Walk to Chesapeake Bay

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

Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

Family and Pet-Friendly, Waterfront with Pier

Waterfront, cozy cottage with private pool on 27 acres

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

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

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

Private waterfront cottage with pool on Church Creek

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Top trending hotels in Taylors Island

Hyatt Regency Chesapeake Bay
Taylors Island Cottages For Rent
Dreaming of a getaway that’s reminiscent of a fairytale? Travelocity doesn’t have magic wands or talking animals in our inventory—at least, none that we can find—but we do have holiday cottages in Taylors Island that will make you feel like you’ve stepped inside your vacation dreams.
The word “cottage” may make you think of whitewashed walls, flower print curtains, and sprawling views of rolling green hills—lucky for you, we do offer tons of country cottages that were furnished with a rustic feel in mind. Appreciate the vase of daffodils on your dining room table, and peek out the window onto the private patio that surrounds yours and other rustic cottages in the area.
These charming “home away from homes” have long been a beacon for those who love the outdoors, so pick a spot peppered with hiking trails and spend lazy afternoons meandering through the gorgeous scenery Taylors Island is known for. Snap some pictures while you’re at it—you’ll want to remember sunset over this waterfall for the rest of your life. When the sun goes down, cuddle up in front of a cheerful fire, or head into town to explore the shops, restaurants, and art galleries that have sprung up over the years. Ah, it’s nice to return to civilization every once in a while, isn’t it?
Whether you select cottages minutes away from the bustling city center, or coastal cottages that are footsteps from the sand and surf, you’ll find the accommodation you’re looking for here on Travelocity. Just because you’re booking a place that reminds you of a fairytale doesn’t mean you need a fairy godmother to find the best deal around! Just a gnome…
Taylors Island Cottages essential information
Accommodation | 62 Cottages |
---|---|
Lowest Price | |
Highest Price | |
Popular accommodation | Waterfront Cottage in Beautiful Hoopers Island, North Beach Cottage - Walk to Chesapeake Bay, Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE, Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit, Family and Pet-Friendly, Waterfront with Pier, Waterfront, cozy cottage with private pool on 27 acres , Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣, Cozy Cottage with access to and partially obstructed views of the bay., "Point of View" Waterfront cottage with panoramic views on Tilghman Island, Private waterfront cottage with pool on Church Creek, Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC, Cottage at Goose Neck Point |