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Check prices for these dates

Next weekend
Feb 28 - Mar 2
In two weeks
Mar 7 - Mar 9
In one month
Mar 21 - Mar 23
In two months
Apr 18 - Apr 20

Browse Select Madison Villas

New Construction Greenport Pool House - 3 Blocks from Town
Outdoor pool, a heated pool

New Construction Greenport Pool House - 3 Blocks from Town

New Construction Greenport Pool House - 3 Blocks from Town
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Outdoor pool, a heated pool

1.5 Acre Luxury Escape - Saltwater Pool with Water Views

10.0 out of 10, Exceptional, (1)
"Very nice house In great shape and outstanding pool area."
1.5 Acre Luxury Escape - Saltwater Pool with Water Views
Dove Haven | Find your Peace
Terrace/patio

Dove Haven | Find your Peace

9.8 out of 10, Exceptional, (10)
"Beautiful home - well-appointed and lots of thoughtful attention to detail. We had a great comfortable stay."
Dove Haven | Find your Peace
Luxurious beach house on the Long Island sound
Living area

Luxurious beach house on the Long Island sound

Luxurious beach house on the Long Island sound
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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Other property types in Madison

New Madison beach house - Ocean front- Great views- booking Summer 2025
Exterior

New Madison beach house - Ocean front- Great views- booking Summer 2025

10.0 out of 10, Exceptional, (56)
"Great location "
New Madison beach house - Ocean front- Great views- booking Summer 2025
New Haven Village Suites
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (2005)
"Easy fast check in"
The price is CA $125
CA $144 total
includes taxes & fees
Mar 3 - Mar 4
New Haven Village Suites
Postcard Cabins Machimoodus
Exterior

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (6)
"I loved this escape from reality. This was a very quiet romantic getaway for Valentine’s Day. The place was very clean and had everything we needed from a fully equipped small kitchen to everything outdoors we would need for a campfire and making s’mores. I loved this place and can’t wait to come back for another romantic getaway."
Postcard Cabins Machimoodus
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.

Frequently asked questions

Why book your villa in Madison with Expedia?
We think that vacations shouldn’t be difficult, so if you’re searching for villas at an affordable price, Expedia has your back. Keep the budget in check and pick an all-inclusive stay, or splurge on a high-end villa to spoil the ones you love most. Take advantage of our search filters to find a retreat in Madison that suits your needs.
How can I find cheap villas in Madison?
With Expedia’s user-friendly filter tool, comparing cheap villas in Madison is a cinch. To discover properties that are easy on the wallet, fine-tune your search by amenities, star rating and budget.
What is there to do near my villa in Madison?
There are plenty of fantastic things to do and see in Madison. Drop by well-known attractions like Hammonasset Beach State Park, Hammonasset Beach and Allis-Bushnell House and Museum. Anna Mia’s, RJ Julia Booksellers and Meigs Point Nature Center are other must-do’s.