Madison Vacation Rentals

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Make Madison your next getaway

Madison, CT vacation rentals

Top Madison property types

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House rentals

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Apartments

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Studios

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Popular amenities for Madison vacation rentals

Popular
Dog-friendly Internet Pool
Quiet Killingworth Rental w/ Deck & Grill!

Quiet Killingworth Rental w/ Deck & Grill!

Apartment in Madison

$177 avg / night

5.0 (4)
Private Pool! Getaway, 14 Mi to Hammonasset Beach

Private Pool! Getaway, 14 Mi to Hammonasset Beach

House in Madison

$551 avg / night

5.0 (1)
Walk to Coast! Convenient Cottage in Dtwn Madison

Walk to Coast! Convenient Cottage in Dtwn Madison

Studio in Madison

$207 avg / night

5.0 (1)
2 Mi to Dtwn: 2-Acre Retreat w/ Large Yard!

2 Mi to Dtwn: 2-Acre Retreat w/ Large Yard!

House in Madison

$441 avg / night

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Listings nearby Madison

Waterfront Cottage w/ Sunroom + Patio & Grill

Waterfront Cottage w/ Sunroom + Patio & Grill

Cottage in Clinton

$230 avg / night

Guilford Carriage House at Granite Lodge!

Guilford Carriage House at Granite Lodge!

Cottage in Guilford

$307 avg / night

5.0 (8)
Cozy Westbrook Vacation Rental - Walk to Beach!

Cozy Westbrook Vacation Rental - Walk to Beach!

House in Westbrook

$356 avg / night

5.0 (1)
Historic Essex Home w/ Large Yard Near Downtown!

Historic Essex Home w/ Large Yard Near Downtown!

House in Essex

$313 avg / night

4.91 (11)

Vacation rentals near Madison

Browse more vacation rental amenities in Madison

Ocean view
Water view
Waterfront
A/C
Washer/dryer
Balcony
Beach access
Kayaks
Snowbird-friendly

Recent Madison guest reviews

Studio had everything we needed for a few days away. Beach towels, full kitchen set up, cozy comforter & comfortable place to relax. It was great to be behind Bar Bouchée restaurant- food was amazing! We will be back in the Fall for a bit of leaf peeping on the shore.
Christina . | May 2026
My husband and I enjoyed this wonderful place so much! The apartment was furnished beautifully and had all the little touches that makes a stay away from home comfortable and livable. Everything was so clean and modern including the lovely bathroom. The animals and the pond and the pretty landscape was so relaxing. The owners were also very accommodating and especially kind to our grandkids. It wasn't far from anything but it felt far away which was a good thing! I highly recommend this.
Rhonda . | Aug 2025
What a beautiful, peaceful farm. It was just what I needed. The lil touches were wonderful, and the decor was lovely. I was very fortunate to find this quiet oasis, and so grateful. Thank you Susanne!
Patricia . | Jul 2025
A very peaceful setting, clean and comfortable. Highly recommend this!
Janice . | Jul 2025
Madison vacation rental FAQ

Yes. 14 of our Madison vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Madison vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Madison team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Madison, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

Nearby destinations

New England
Clinton
Guilford
Killingworth
Westbrook
Chester
Essex
Branford
Old Saybrook
Old Lyme
East Haven
East Marion
New Haven
Southold
Greenport
Orient
West Haven
Cutchogue
East Lyme
Shelter Island
Mattituck
Laurel
Aquebogue
Waterford
Milford
Sag Harbor
Riverhead
Montville
New London
Groton
Rocky Point
Bridgehampton
Water Mill
Stratford
Hampton Bays
Wainscott
Southampton
Connecticut