Book St. Michaels, MD Cottages

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Top Cottages in St. Michaels

Don't see what you're looking for?
See all available properties in St. Michaels
View all properties
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.

Top hotels in St. Michaels

St. Michaels 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 St. Michaels 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 St. Michaels 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…

St. Michaels Cottages essential information

Accommodation
72 Cottages
Lowest Price
$105
Highest Price
$645
Popular accommodation
Amazing views, short walks to great dining!, Relaxing Waterfront Cottage Near St Michaels, Maryland, Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays, , Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC., "Point of View" Waterfront cottage with panoramic views on Tilghman Island, Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town, NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak, Perfect family / friend getaway. Kayaks and bikes provided. Walk to Herrington H, Secluded Cozy Cottage in Historic Downtown, 6 Mi to Dtwn: Family-friendly Home in Annapolis!