Compare St. Michaels Cottage Rentals

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Featured Cottages in St. Michaels

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

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden. Helpful staff is there to provide concierge services, as well as offer insight about the area.

Kitchen

Washer

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.

Kitchen

Washer

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.

Pool

Kitchen

Guests staying at this cottage enjoy a hot tub, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.

Hot Tub

Breakfast included

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.

Pool

Kitchen

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Guests staying at this cottage enjoy a sauna, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.

Kitchen

Washer

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.

Pool

Kitchen

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

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.

Kitchen

Washer

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.

Pool

Kitchen

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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.

Hotel Options in St. Michaels

St Michaels Inn

1228 S Talbot Street St. Michaels MD

$89 nightly

$98 total

Oct 7 - Oct 8

Total with taxes and fees

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD

$670 nightly

$737 total

Sep 29 - Sep 30

Total with taxes and fees

The Wildset

209 N Talbot St St. Michaels MD

$262 nightly

$288 total

Sep 22 - Sep 23

Total with taxes and fees

9.8/10 Exceptional! (510 reviews)

Cottages

Book a cottage in St. Michaels
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in St. Michaels. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know St. Michaels better.

Cottage apartments in St. Michaels range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in St. Michaels
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in St. Michaels and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a St. Michaels cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in St. Michaels. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

St. Michaels Cottages essential information

Accommodation	94 Cottages
Lowest Price	$98
Highest Price	$737
Popular accommodation	Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE, Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, Firefly Cottage at the Cape, Hot Tub, Community beach, Boat Show, USNA Football., John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly, Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town, Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly), Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch