Madison rentals with pool

We found 356 rentals with pool — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any holiday rentals with a pool in Madison?
Check out our 356 holiday rentals with a pool and start making plans for your Madison trip. Whether you want to be in Eidelweiss Village, Chocorua, Chocorua Ski and Beach or another well-known neighbourhood, you'll find the perfect poolside escape on Stayz.
How much does it cost to stay in a holiday rental with a pool in Madison?
It doesn't get much better than a holiday rental with a pool, and it doesn't have to be costly with Stayz. While many factors will impact how much you'll pay for your getaway in Madison, our filters will help you find the best deal. Choose your budget and use our "Discounts" filter to search for properties that offer savings for longer stays. With an inviting pool ready for you to dive into, you'll want to settle in as long as you can.
When is the best time to book a holiday rental with a pool in Madison?
With average temperatures ranging from 3ºC to 14ºC, October is popular with most Stayz guests. Make sure you check out our holiday rentals with a pool in this part of Lakes Region at other times too. You may find more availability if you avoid Madison's peak months.
What holiday rentals with a pool in Madison have nice views?
From lounging poolside to practicing your cannonballs, a holiday rental with a pool promises endless hours of fun by the water. Add some outstanding views and you'll never want your break to end. Use our convenient filters to tailor your search for a stay in Madison that comes with the amenities you want and vistas that inspire wonder.
Are there holiday rentals with a private pool in Madison?
Night or day, enjoy a swim whenever you want when you book a holiday rental with a private pool in Madison. To look for accommodation that'll bring an extra dose of fun to your escape, use our "Private pool" filter.
What are the top things to do in Madison?
It's no surprise why families love Madison, with top-rated attractions like Cranmore Mountain Resort, Settlers' Green Outlet Village and Conway Scenic Railway to explore. Discover this destination's best sights together and then return to the comforts of your holiday home rental.
Why should I book my holiday rental with a pool with Stayz?
When you book a holiday rental with a pool with Stayz, you'll get more than the standard hotel experience — think a private space with a place to relax by the water. You're also covered by our Book with Confidence Guarantee. This means we're here to guarantee a hassle-free stay throughout your entire trip. Have an unforeseen change of plans? Check out our cancellation policies to find out if you are eligible for a complete refund.
Rentals with Pool in Madison
Rentals with Pool in Eidelweiss Village