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Featured Madison Cottages

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay

The price is $298 per night
$298
includes taxes & fees
$281 per night
May 5 - May 6
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
Cozy Cottage with access to and partially obstructed views of the bay.

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

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Waterfront Cottage in Beautiful Hoopers Island

Waterfront Cottage in Beautiful Hoopers Island

Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Pet friendly
Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

At this cottage, guests have access to an outdoor pool, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
Pool
Kitchen
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

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
Eastern Shore Waterside Cottage Near St. Michaels

Eastern Shore Waterside Cottage Near St. Michaels

At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Pool
Kitchen
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

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

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

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Pool
Kitchen
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

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

Guests staying at this cottage enjoy a water park, a hot tub, and laundry facilities. Other amenities at this family-friendly cottage include a garden and barbecue grills.
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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 Madison

    Hyatt Regency Chesapeake Bay

    Hyatt Regency Chesapeake Bay

    100 Heron Blvd, Cambridge, MD
    The price is $275 per night from May 6 to May 7
    $275
    includes taxes & fees
    $242 per night
    May 6 - May 7
    8.6/10 Excellent! (1,000 reviews)
    Inn at Perry Cabin

    Inn at Perry Cabin

    308 Watkins Ln, St. Michaels, MD
    The price is $583 per night from May 4 to May 5
    $583
    includes taxes & fees
    $530 per night
    May 4 - May 5
    9.4/10 Exceptional! (344 reviews)
    St Michaels Inn

    St Michaels Inn

    1228 S Talbot Street, St. Michaels, MD
    The price is $155 per night from May 4 to May 5
    $155
    includes taxes & fees
    $141 per night
    May 4 - May 5
    8/10 Very Good! (1,001 reviews)

Cottages

Book a cottage in Madison
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Madison. 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 Madison better.

Cottage apartments in Madison 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 Madison
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 Madison 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 Madison 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 Madison. 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.

Madison Cottages essential information

Accommodation
65 Cottages
Lowest Price
$155
Highest Price
$583
Popular accommodation
Soul Oasis - home on the Chesapeake Bay, Cozy Cottage with access to and partially obstructed views of the bay., Waterfront Cottage in Beautiful Hoopers Island, Family and Pet-Friendly, Waterfront with Pier, Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, Eastern Shore Waterside Cottage Near St. Michaels, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town, Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

Cottages in Madison

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