Madison vacation rentals

We found 1,276 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024
Select from 59 homes, 13 cottages, and other vacation rentals in Madison to find one that's perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the best amenities for hanging out with the people that matter most, which might include a garden and WiFi. No matter what you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Madison is a gateway to outdoor adventure

Discover New Hampshire’s most exciting outdoor adventures and an array of natural attractions with a stay in Madison. Whether you’re spending summer days swimming beneath a mountain waterfall, or taking breathtaking trips on the Conway Scenic Railroad amid blazing fall colors, you’ll be beguiled by the landscape. Come winter, you can go skiing and snowboarding down picture-perfect powdery slopes. Madison vacation rentals include everything from rustic cabins and village chalets to grand waterfront homes and secluded hideaways in the White Mountains, so it’s never been easier to experience this exciting part of the world.

Marvel at the Madison Boulder

Natural attractions are plentiful here, but taking center stage is the Madison Boulder. Scientists haven’t reached agreement about where this giant rock came from, only that a glacial drift swept it to its current location during the last ice age. Either way, this magnificent beast - thought to weigh the same as almost 40 blue whales - must be seen to be believed. Of course, not all New Hampshire’s attractions are of the natural variety. Barnstormers Theatre, an intimate space offering performances from June through August, and the bars and restaurants along the White Mountain Highway, help to turn action packed days into laidback nights.

Going for a dip in natural grandeur

If you’ve chosen a Madison vacation rental overlooking Silver Lake, then swimming in the crystal-clear water before topping up your tan at Nichols Beach is a must. Several lakeside companies offer kayak and canoe hire during the summer, should you fancy trying something different. In the nearby White Mountains National Forest, activities take on a different flavor. Hikes, for example, range from easy jaunts to the waterfall and swimming hole at Diana’s Baths, to the more strenuous trek to the top of Mount Washington. Feeling the wind in your hair as you speed down the Cranmore Mountain Coaster is another must for your bucket list.

Explore Madison’s diverse backyard

Madison vacation rentals offer a great base from which to explore a wide variety of landscapes. Day hikes can be the best way to enjoy the area’s diversity as you take on routes such as Cathedral Ledge, Tuckerman's Ravine, and Hedgehog Mountain. If strenuous hiking isn’t really your thing but you’d still like to soak up the beauty of the area, there are many stunning waterfalls within an hour’s drive of Madison. Those that are easy to reach include Rocky Gorge, Sabbaday Falls, and Flume Cascade. In the winter, the landscape is transformed, and skiing trails at the likes of Wildcat Mountain and Shawnee Peak beg to be discovered.

Transportation to and around Madison

The nearest airport is in Portland Intl. Jetport Airport (PWM), located 45.3 mi (72.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Fryeburg, ME (FRY-Eastern Slopes Regional), which is 11.7 mi (18.8 km) away.

Frequently asked questions

What is the best area to stay in Madison when booking a vacation rental?

If you're planning to explore Madison, Eidelweiss Village is one of the most in-demand locations to stay. Whatever your travel style, Vrbo is sure to have a vacation property here that has everything you need.

What is the most popular type of vacation rental accommodation in Madison?

The most desirable types of vacation rentals in Madison are houses. Prefer something different? Vrbo has many options to match our guests' unique needs, so you'll see vacation properties in lots of shapes and sizes. The perfect home away from home is waiting for you — discover yours today.

How much does it cost to rent a vacation rental in Madison?

Different things determine how much you pay for a vacation rental in Madison, including the length of stay, season and type of property. But, all of our vacation homes have something in common — amazing value. Just enter your travel dates to find your home away from home.

How much does it cost to rent a beach house in Madison?

Prices for beach houses in Madison may differ depending on the size and style of the property and when you plan to travel. All you need to do is enter your travel dates into Vrbo and how many guests to see your rental options and prices. From there you can use the filters to tailor your search by ratings, nearby activities, amenities and more.

Are there pet-friendly vacation rentals in Madison?

Yes. You can pick from 113 vacation rentals that allow pets in Madison. Plenty of our pet-friendly vacation rentals even come with a garden for your fur baby to have fun in, doggie beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find your place on Vrbo.

Can I rent a house with a pool in Madison?

Pack your swimwear and inflatable swan, because there are 15 houses with a private pool in Madison. Kick back at one of these sought-after vacation rentals and let every day be a pool day. Simply enter your dates into Vrbo, then use the "pool" filter to find the perfect place to make a splash!

What are popular rental amenities in Madison?

Some of the most popular rental amenities people prefer in Madison include a barbecue grill, a garden and mountain views. Whether you're taking a trip with your besties, family or even pets, Vrbo vacation rentals include the best amenities for fun and relaxation with the people you love.

Are there large group vacation rentals in Madison?

There are 38 vacation rentals in Madison that can sleep 10 or more guests. Whether you're planning a vacation with extended family or a special event, there's plenty of space to get your group together under one roof.

Are there vacation rentals in Madison that welcome kids?

With 112 family-friendly vacation properties available in Madison, now is a fantastic time to introduce the little ones to the magic of travel. Click on our "Properties good for families" filter box to locate stays that come with amenities ideal for vacationing families, like full kitchens, patios, bunk beds and entertainment units.

What are the top attractions for families in Madison?

Keeping the kids happy during your stay in Madison is a snap with these exciting family-friendly attractions:

  • Conway Station
  • Silver Lake Railroad
  • Remick Country Doctor Museum and Farm

Are there one-bedroom vacation rentals in Madison?

There are three one-bedroom properties in Madison to select from. A one-bedroom vacation home is a wonderful choice if it's just you and your sweetheart or if you're traveling on your own. Add in more space, privacy and convenience than a standard hotel, and you've got the makings of a memorable trip.

Can I find two-bedroom vacation rentals in Madison?

Madison has 15 two-bedroom vacation rentals for you to select from. Go for a vacation home with all the comfort and privacy you're looking for at a fantastic price on Vrbo.

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