Compare St. Michaels Cottage Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured St. Michaels Cottages

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.

St. Michaels Beach Accommodation

    Inn at Perry Cabin

    Inn at Perry Cabin

    308 Watkins Ln, St. Michaels, MD
    The price is $403 per night from Feb 26 to Feb 27
    $403
    includes taxes & fees
    $366 per night
    Feb 26 - Feb 27
    9.4/10 Exceptional! (331 reviews)

Hotel Options in St. Michaels

    Inn at Perry Cabin

    Inn at Perry Cabin

    308 Watkins Ln, St. Michaels, MD
    The price is $403 per night from Feb 26 to Feb 27
    $403
    includes taxes & fees
    $366 per night
    Feb 26 - Feb 27
    9.4/10 Exceptional! (331 reviews)
    St Michaels Inn

    St Michaels Inn

    1228 S Talbot Street, St. Michaels, MD
    The price is $94 per night from Mar 16 to Mar 17
    $94
    includes taxes & fees
    $85 per night
    Mar 16 - Mar 17
    8/10 Very Good! (1,001 reviews)
    The Wildset

    The Wildset

    209 N Talbot St, St. Michaels, MD
    The price is $241 per night from Feb 24 to Feb 25
    $241
    includes taxes & fees
    $219 per night
    Feb 24 - Feb 25
    9.6/10 Exceptional! (298 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
78 Cottages
Lowest Price
$94
Highest Price
$403
Popular accommodation
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, "Point of View" Waterfront cottage with panoramic views on Tilghman Island, Relaxing Waterfront Cottage Near St Michaels, Maryland, Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, Enchanting West River Retreat, 6 Mi to Dtwn: Family-friendly Home in Annapolis!, Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb, Pet-friendly Annapolis Home: Walk to Beach!