
Holiday rentals in Madison
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Top-rated holiday rentals in Madison
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Other great holiday rentals in Madison
Superhost

Cottage in Clinton
4.83 out of 5 average rating, 40 reviewsThe Beach Nest-Lux Cottage Steps to the Beach
ChrisRating, 5 stars1 month ago
Great, beachy location within easy driving distance of a bunch of great waterfront restaurants. Easy, clean, and very comfortable.

Home in Madison
4.75 out of 5 average rating, 4 reviewsSea La Vie - Beachfront Private Home
NancyRating, 5 stars9 months ago
The setting right on the beach was perfect and very quiet and private! Loved being able to enjoy the views from inside as well as the great deck. The house was extremely comfortable and well equipped. It was the perfect setting for a great relaxing week and look forward to renting it again. It was also close to downtown Madison and great restaurants! Lori was very responsive to any questions etc!
Guest favourite

Home in Madison
4.93 out of 5 average rating, 15 reviewsFabulous pool in beach town!
DovidRating, 5 stars9 months ago
We took the house for a family getaway, and it far beyond surpassed our expectations. From the cleanliness of the home, to the beauty and utility of the pool. There was an abundance of all things you can expect to find in a home, e.g. the bathrooms were stocked with an abundance of name brand shampoos and soaps. We enjoyed the beautiful coastline that was in close proximity to house. And we spent hours at the pool on a daily basis, it was very private. Cindy was responsive to our every need and query. She even came by a couple of times to help us out with some issues, she went beyond her call of duty. All this she did graciously, as if it’s not even a bother. She is a true super host.
Guest favourite

Cottage in Guilford
4.95 out of 5 average rating, 80 reviewsDirect Shoreline Long Island Sound Waterfront
ThomasRating, 5 stars9 months ago
Our visit was utilitarian. We needed accommodations for us, our grown children and grandchildren and a dog. But the site of the cottage, its charm, its comfort made us wish we were staying another week. James' thoughtfulness went beyond any other Airbnb hosts' that we've experienced. Everything we might need if we were staying 10 days was there, clean, labeled. Thank you, James.
Top guest favourite

Guest suite in Clinton
5 out of 5 average rating, 5 reviewsPrivate 2-room suite + bath in beach town
LizzieRating, 5 stars2 weeks ago
We had a great time! The unit is very clean and comfortable and has everything you would need. The unit is exactly as pictured and described. The outdoor amenities (hot tub, deck and grill) are a huge bonus. The outdoor space is so calm and serene. The neighborhood is very quiet and peaceful and there are plenty of food/dining options within driving distance in lieu of a full kitchen (which is already described). Delicious lobster rolls are only a few minutes away via car which is great! While we were there we visited Lake Compounce as well as the USS Nautilus - that was fun! Suzanne is such a kind and wonderful host. She made our stay extra pleasant and was always available to answer questions or provide anything necessary. She provided a snack basket which came in handy and was much appreciated. Her dog,Molly, is a sweet dog and we enjoyed her company. We are so grateful for Suzanne and her warm hospitality :) Thank you once again!

Guest suite in Madison
4.88 out of 5 average rating, 8 reviewsVintage Cabin Suite with full kitchen (No.2)
JerryRating, 5 stars6 months ago
There was a problem caused by skunk spray, hardly anything controllable by the innkeeper. Amanda handled our need to leave promptly, politely, and professionally.
Guest favourite

Loft in Guilford
4.98 out of 5 average rating, 61 reviewsWaterfront Apartment-Guilford CT-***New Listing
VincentRating, 5 stars1 week ago
Quiet stay at Kim's place, perfect for a quick coastal getaway. Relax on the deck to the sound of the ocean, then enjoy the Guilford area.
Guest favourite

Flat in Clinton
4.81 out of 5 average rating, 21 reviewsBright & Cozy Loft Near Beach
ErickaRating, 5 stars1 week ago
Diana's place was an absolute joy to stay in. The serene surroundings were just beautiful. So quiet and the perfect getaway to unplug. Lots of local restaurants to choose from as well! Highly recommended staying here!
Quick stats about holiday 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
Destinations to explore
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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Napeague Beach
- Cooper's Beach, Southampton
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Ocean Beach Park
- Woodmont Beach
- Amagansett Beach
- Seaside Beach
- Blue Shutters Beach
- Quotonset Beach
- Ninigret Beach
- Bushnell Park
- Calf Pasture Beach
- Heckscher State Park
- Jennings Beach
- Silver Sands Beach
- Sunken Meadow State Park