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Vacation rentals in Madison

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Popular amenities for Madison vacation rentals

Stay near Madison's top sights

Hammonasset Beach State Park173 locals recommend
Clinton Crossing Premium Outlets109 locals recommend
Chamard Vineyards Bistro63 locals recommend
Lobster Landing39 locals recommend
RJ Julia Booksellers35 locals recommend
The Place Restaurant31 locals recommend

Other great vacation rentals in Madison

Guest favourite
Home in Montville
4.89 out of 5 average rating, 62 reviews

Hidden Gem Quite Dead-end St Near All Casinos

TaTanishaRating, 5 stars1 month ago
Great place to stay clean and close to the event we went to… they were helpful and allowed us to stay 1 hr longer for our convenience… there was only one TV in the house so if you have kids make sure they have their tablets or they will control the one TV other than that it was enough space for us…. Thanks
Guest favourite
Home in New Milford
4.94 out of 5 average rating, 32 reviews

Serene Country home 24 mi Mohawk ski area

ConnieRating, 5 stars1 month ago
A beautiful home- super comfortable and spacious. It is outfitted with everything you could need. Peaceful location (we stayed in spring/winter- can’t speak to what it would be like in season). Lovely views. Easy to get into town by car (3-5 minutes!). Host was excellent - responsive to any questions or inquiries
Top guest favourite
Cottage in Guilford
4.99 out of 5 average rating, 136 reviews

"Red House on the Knoll" at Indian Cove

MaryRating, 5 stars2 weeks ago
My family and I loved staying at Gail’s place! We grew up in Madison and were back for a visit. It was such a great place and allowed us to re-live many fond memories of growing up in the area!
Superhost
Home in Waterford
4.94 out of 5 average rating, 18 reviews

Summer Beach Cottage Harknes, Ocean Beach N

JenniferRating, 5 stars7 months ago
It was a perfect spot for our little family vacation. We were so close to a few really nice beaches and the area is a short drive to mystic aquarium and village. Patsy and family are very nice and gave some great suggestions for activities in the area.
Guest favourite
Cabin in Rocky Point
4.89 out of 5 average rating, 485 reviews

Great little place just for a couple

PaulRating, 5 stars3 days ago
The property was cozy and clean with great graden sitting are and almost everything you could need. Only qualm was that the property was advertised to have a fence but there isn’t one, there is a hedge but not a gate to make an enclosed space for a dog. This isn’t a huge deal because the beach is so close and great for walks just a minor disappoint other than that the place is incredibly cozy and we would be happy to stay here again
Guest favourite
Guesthouse in Shelter Island
4.96 out of 5 average rating, 27 reviews

Sleek and Chic cottage/Pool House

YuryRating, 5 stars11 months ago
Perfect getaway in Shelter Island! The pool house is as amazing as it looks in the listing :) Cute house on a beautiful, peaceful and very private green lot. Primael was very welcoming and responsive. She was also very flexible in terms of our check in and check out. Everything went super smoothly. We enjoyed our stay a lot!
Guest favourite
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars4 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!
Top guest favourite
Home in Old Saybrook
5 out of 5 average rating, 49 reviews

Great Hammcock Getaway, Nearby beaches, Hot tub

DavidRating, 5 stars1 month ago
What a beautiful place and conveniently located. The house was wonderful decorated, was very comfortable and definitely was a relaxing place to get away. Irina was a wonderful host and the home had many wonderful amenities to offer.

Quick stats about vacation rentals in Madison

  • Total rentals

    130 properties

  • Total number of reviews

    4.2K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

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