Madison Holiday Rentals from €354: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Madison has to offer?

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock : This holiday home rental outside of Madison is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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Holiday Rentals in Madison

"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "

"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "

"This house has the perfect location to explore the town. We stayed in this house for the St. Michael’s Running Festival and it couldn’t have been better. The location was so close to the start/finish lines and there were so many restaurants within a few minutes walk. "

"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."

"Awesome home wnd location! Would stay again!"

"This house was just what we needed for our business associates. "

"Great House "

"The views are fantastic. Very quiet neighborhood. "

"Wow, what a homerun of a vacation house - it had everything we needed and more. We had the best time and hope to be back soon."

"This house is awesome - very large and has room for all! It also has some old charm character and features that were really fun, like two "hidden staircases" the kids loved! Bedroom layouts were smartly planned to accommodate large groups and families. The property is truly gorgeous and huge - trails in the woods, lakes, tons of space for yard games and a swing set with two working swings. Parking was abundant, great basketball court and well stocked with the basics! The indoor pool is literally...

"Clean and nice place to stay"

"We had a very nice stay and enjoyed the quiet environment and the amenities of the property. Lots of great area for walking. "

"Highly recommend this apt. Beautifully renovated and very spacious! Location is centrally located and very quiet on the inside. I ended up staying another night because we enjoyed so much!"

"We once again enjoyed our stay here. Perfect location to every where you’d want to go in St. Michael’s! Loved sitting out front looking at the water and park and enjoying music from our front yard. Highly recommend this cottage."

"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "

includes taxes & fees

4 Sept - 5 Sept

"Good location, clean house, easy check in and check out process."

"Clean, well-appointed kitchen. Loved the crab shack!! Would highly recommend. Used the kayaks and canoe. The pool was perfect! The property is beautiful. Highly reccomend"

"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."

"Stayed for the weekend- parked the car and could walk to everything- perfect. Host was super responsive and the place was super clean!"

"We sought a large home for a special family birthday, with multiple bedrooms, roomy eating and living areas, and water access for recreation. This house met all our requirements and more. Our grandchildren, from teen to preschool, loved the multiple kayaks, the crab traps, roasting marshmallows at the fire pit, swimming in the heated pool, finding oyster shells along the shoreline. We visited Annapolis for a sail and sightseeing, even though it meant driving back over the Bay bridge, and we...

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Everything you need to know about Madison holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Madison holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Madison holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Madison holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Madison. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Madison holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Madison holiday rentals we have selected for you start as low as €354 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Madison rentals

At Expedia, we put the best Madison holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Madison rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Madison holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Madison. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there holiday rentals in Madison?

Yes, there are holiday rentals close to the most popular sights in Madison, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Madison has to offer?

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock: This holiday home rental outside of Madison is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

What’s there to see and do in Madison?

Explore the area and family-friendly sights such as Richardson Maritime Museum, or get out into nature at a spot like Blackwater National Wildlife Refuge. Harriet Tubman Underground Railroad National Historical Park and Harriet Tubman Museum and Educational Center are a couple of places you'll find in the wider area.

What’s a holiday rental in Madison like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Madison. Holiday rentals provide amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family gatherings.

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Holiday Rentals in Madison

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Holiday Rentals in Madison

Family and Pet-Friendly, Waterfront with Pier

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

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

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

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

4BDRM River front house with Private Beach in Hollywood

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Walk to Everything House

Waterfront Cottage in Beautiful Hoopers Island

Modern Flat in the Heart of St. Michaels – Walk Everywhere

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

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

"Belle Aire Landing" a Large Beautiful Waterfront Estate! Under New Management!

Dollhouse in Central Historic St Michaels

Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

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