Madison Vacation Rentals from $856: Search Short-Term Rentals

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

Private 2 Acre Waterfront Family Retreat with Pool & Pier : This vacation home rental outside of Madison is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

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Our top choices for Madison vacation rentals

A living room with two grey sofas, a coffee table, and a ceiling fan.

1. Cambridge Apt in Walkable Neighborhood

Cambridge

LOIS

$291 nightly

Oct 17 - Oct 18

Total with taxes and fees

2. Cambridge Apt in Walkable Neighborhood

Cambridge

Anonymous traveler

$298 nightly

Oct 17 - Oct 18

Total with taxes and fees

A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

3. Waterfront Getaway with Dock

Woolford

Meagan G.

$229 nightly

Oct 18 - Oct 19

Total with taxes and fees

A spacious living room with a large TV, blue sofa, and a ceiling fan.

4. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford

Joyce F.

$632 nightly

Oct 14 - Oct 15

Total with taxes and fees

A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

5. Sailwinds Loft at Cambridge Creek

Cambridge

Sharon D.

$240 nightly

Oct 18 - Oct 19

Total with taxes and fees

A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

6. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Downtown Cambridge

Kristen S.

$352 nightly

Oct 12 - Oct 13

Total with taxes and fees

A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

7. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

Nancy P.

$246 nightly

Oct 19 - Oct 20

Total with taxes and fees

A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

8. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8

Cambridge

Jill C.

$526 nightly

Oct 14 - Oct 15

Total with taxes and fees

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Top Madison Hotel Reviews

Baymont by Wyndham Easton

10/10 Excellent

"Clean, convenient location, very friendly staff, good breakfast. Will book here again. Thanks."

St Michaels Inn

10/10 Excellent

"We travel to St micheals md, several times a year, during the oyster season. Usually we stay at hotels in easton, so this time we tried the st micheals inn. It's closer to the Cheasapeake Landing restaurant. We were placed in a room opposite the main street, which made for a very quiet evening. Much better than those hotels off rt.50. The breakfast was a "hot" breakfast and included with the stay. The beds are comfortable, and the showers hot and forceful."

Find out more about Madison

Everything you need to know about Madison vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Madison vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Madison vacation 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 low season months. For more hustle and bustle, you may prefer to visit Madison in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $856 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Madison rentals

At Expedia, we put the best Madison vacation 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 vacation.

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 vacation rentals in Madison?

Yes, we offer vacation rentals near top attractions in Madison, or you can go with a more secluded option if you want a relaxing place to stay.

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

Private 2 Acre Waterfront Family Retreat with Pool & Pier: This vacation home rental outside of Madison is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

How many vacation rentals will I find in Madison?

Choose from 3 Expedia vacation rentals in Madison for a memorable vacation.

What’s there to see and do in Madison?

Explore the area and family-friendly sights such as Phillips Wharf Environmental Center, 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 larger area.

What’s a vacation rental in Madison like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Madison. Vacation rentals feature extras like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for family trips.

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Our top choices for Madison vacation rentals

1. Cambridge Apt in Walkable Neighborhood