Holiday Homes in Madison

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Featured Holiday Homes in Madison

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (30)
"A very comfortable short stay in a convenient location"
Cozy 2 bedroom home located minutes from downtown

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

10.0 out of 10, Exceptional, (102)
"Our multigenerational long weekend loved our stay. Fab manager. House so well kitted out. "
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

McAngel Haven: 5 mins from Yale

9.6 out of 10, Exceptional, (14)
"My family and I stayed at the property for a wedding in Milford. The house had plenty of space for our group to say, and the bedrooms were comfortable. The three bathrooms were helpful for our group to efficiently get ready for the wedding, and the kitchen was adequately appointed for us to have meals."
The price is AU$796
includes taxes & fees
29 Sept - 30 Sept
McAngel Haven: 5 mins from Yale

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

9.4 out of 10, Exceptional, (14)
"This Carriage House is exactly as described. Wonderful location and setting, just steps away from Branford Point. Hope to visit again soon! "
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

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

10.0 out of 10, Exceptional, (67)
"The house is perfectly located. Quiet area but close to downtown Madison and Guilford and so much the CT shoreline has to offer. "
New Madison beach house - Ocean front- Great views- booking Summer 2025

The SandPiper

9.8 out of 10, Exceptional, (25)
"My wife and I stayed at the Sandpiper for a long weekend. The property was very clean with a warm welcoming feeling. It is within walking distance to the beach and downtown shopping. Great location. I would recommend it to everyone."
The SandPiper

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (14)
"the host was really great about getting back to us when we had a question or problem . his home was comfortable and artistic. the location was also easy to get to and the neighborhood was quiet and comvenient to all your needs."
Ranch style living at its best with country garden & patio!

Sea Breeze Paradise: Beachfront & Panoramic Views

9.8 out of 10, Exceptional, (6)
"Everything was perfect, very comfortable and the location was outstanding."
Sea Breeze Paradise: Beachfront & Panoramic Views

I’ve had the best guests!

10.0 out of 10, Exceptional, (26)
"House was beautiful - clean -perfect to hang in - pool was great, very private and relaxing - host was hospitable, friendly and accommodating - can’t wait yo go back in the fall!"
I’ve had the best guests!

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (68)
"Great family get together where we all were very comfortable. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (127)
"Fantastic all around!"
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Aqua Vista

10.0 out of 10, Exceptional, (20)
"Apartment was great for 2 couples and a baby. The location was amazing, 5 min walk to everything! Beds were super comfy!"
Aqua Vista

American Beech in Greenport - Petite King Room 7

9.0 out of 10, Wonderful, (4)
"Great job "
The price is AU$473
includes taxes & fees
2 Oct - 3 Oct
American Beech in Greenport - Petite King Room 7

Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

4.8 out of 10, (3)
"Overall, my girlfriends and I had a good stay at this accommodation. Transparently, there were some hiccups in communication between the property manager and I in the week leading up to our trip that were not clearly stated in the home's description prior to us booking our stay, however, I felt that they were able to address my concerns and came up with solutions that felt satisfactory to my group and I. The property manager was overall understanding and receptive to my feedback through our...
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

Charming beach home, complete with pool & cozy guest house!

9.8 out of 10, Exceptional, (35)
"Very clean and comfy house. The guest cottage was a nice surprise! Walking distance to Beach and restaurants.We were during the recent heat wave and spent a lot of time in the pool.Would return again if in the area."
Charming beach home, complete with pool & cozy guest house!

Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

2.0 star property
10.0 out of 10, Exceptional, (7)
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

10.0 out of 10, Exceptional, (5)
The price is AU$444
includes taxes & fees
1 Oct - 2 Oct
Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

The Beach House - Old Lyme

10.0 out of 10, Exceptional, (19)
"Exquisite botanical garden!"
The Beach House - Old Lyme

Amazing Lakefront Property

9.8 out of 10, Exceptional, (26)
"Great views and a good central location for day trips 👌. "
Amazing Lakefront Property

Clear LI Sound waterview, Wedding pics, Yale&Beach

10.0 out of 10, Exceptional, (7)
"Attended a wedding close by. This house was a comfortable clean place to rest in between events. Lovely water front. Calm and peaceful"
The price is AU$941
includes taxes & fees
5 Oct - 6 Oct
Clear LI Sound waterview, Wedding pics, Yale&Beach
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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Top Madison Hotel Reviews

Find out more about Madison

Find out more about Madison

Madison Holiday Homes information

Number of reviews
583
Accommodation
727 Holiday Homes
Lowest Price
AU$444
Highest Price
AU$941

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