Hot Madison Cottage Rates

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Featured Cottages in Madison

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

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

Port Republic
Located in Port Republic, this cottage is in a rural location, within a 10-minute drive of R&J's PlayPark and Battle Creek Cypress Swamp Sanctuary.
Cozy Cottage with access to and partially obstructed views of the bay.
Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland

Wittman
With a stay at this cottage in Wittman, you'll be on the waterfront, and 7.7 mi (12.4 km) from Phillips Wharf Environmental Center and 8.1 mi (13.1 km) from ...
Relaxing Waterfront Cottage Near St Michaels, Maryland
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

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

Tilghman Island
When you stay at this cottage in Tilghman, you'll be 12 minutes by foot from Tilghman Watermen’s Museum.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
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John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

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

Saint Michaels
With a stay at this cottage in St. Michaels, you'll be a 5-minute walk from St. Michaels Museum and 7 minutes by foot from St. Michaels Winery.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay

Lusby
The price is AU$463 per night from 24 Dec to 25 Dec
AU$463
includes taxes & fees
24 Dec - 25 Dec
With a stay at this cottage in Lusby, you'll be within a 15-minute drive of Calvert Cliffs State Park and Cove Point Lighthouse.
Soul Oasis - home on the Chesapeake Bay
Premier St. Michaels Cottage - T. Blades House -  Walk to Everything in Town

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

St Michaels
With a stay at this cottage in St. Michaels, you'll be within a 10-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Waterfront Cottage in Beautiful Hoopers Island

Waterfront Cottage in Beautiful Hoopers Island

Fishing Creek
Located in Fishing Creek, this cottage is on the waterfront, within a 15-minute drive of Middle Hooper Island and Lower Hooper Island.
Waterfront Cottage in Beautiful Hoopers Island
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

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

St Michaels
With a stay at this cottage in St. Michaels, you'll be within a 10-minute walk of St. Michaels Museum and Chesapeake Bay Maritime Museum.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
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

Saint Michaels
With a stay at this cottage in St. Michaels, you'll be a 5-minute walk from Chesapeake Bay Maritime Museum and 6 minutes by foot from St. Michaels Museum.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
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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.

Madison Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Madison will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Madison definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Madison, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Madison Cottages essential information

Accommodation
49 Cottages
Lowest Price
AU$162
Highest Price
AU$706
Popular accommodation
Cozy Cottage with access to and partially obstructed views of the bay., Relaxing Waterfront Cottage Near St Michaels, Maryland, "Point of View" Waterfront cottage with panoramic views on Tilghman Island, John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Soul Oasis - home on the Chesapeake Bay, Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town, Waterfront Cottage in Beautiful Hoopers Island, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Top trending hotels in Madison

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is AU$365 per night from 13 Jan to 14 Jan
AU$365
includes taxes & fees
13 Jan - 14 Jan 2025
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 6 minutes from Dorchester County Visitors ...
Hyatt Regency Chesapeake Bay
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is AU$706 per night from 9 Jan to 10 Jan
AU$706
includes taxes & fees
9 Jan - 10 Jan 2025
A stay at Inn at Perry Cabin places you in the heart of St. Michaels, within a 15-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.
Inn at Perry Cabin
Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick

3 out of 5
75 Sherry Lane, Prince Frederick, MD
Fully refundableReserve now, pay when you stay
The price is AU$180 per night from 29 Dec to 30 Dec
AU$180
includes taxes & fees
29 Dec - 30 Dec
Located in Prince Frederick, Springhill Suites by Marriott Prince Frederick is within a 10-minute drive of Running Hare Vineyard and Patuxent River.
Springhill Suites by Marriott Prince Frederick
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La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

2.5 out of 5
22769 Three Notch Rd, California, MD
Fully refundableReserve now, pay when you stay
The price is AU$162 per night from 26 Dec to 27 Dec
AU$162
includes taxes & fees
26 Dec - 27 Dec
Located in California, La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent is within a 5-minute drive of Patuxent River Naval Air Museum and Patuxent ...
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
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See all available properties in Madison
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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.

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^Subject to availability and chosen travel dates.