Skip to navigation
Skip to main content
Skip to footer
Madison, CT
Dates
Guests
Favorites
Alerts
Log in
Sign up
Filters
Popular filters
Pets allowed
Accessible
Free Cancellation
Price
$
0
/night
Min price
$
1,000+
/night
Max price
Type of place
Cabin
Cottage
Mansion
House
Hotel
Villa
Boat
Condo
Show more
Rooms & spaces
Bedrooms
Studio
1
2
3
4+
Bathrooms
1
2
3
4
5
6
7
8+
Other spaces
Kitchen
Outdoor space
Workspace
Amenities
Basics
Air conditioning
Laundry
Central heating
Parking
TV
Wifi
Show more
Locations
Lake
Waterfront
Beach
Oceanfront
Ski in/Ski out
Mountains
Accessibility
Only show listings with accessibility features.
Rules & policies
Pets allowed
Smoking allowed
Free cancellation
Price
$
0
/night
Min price
$
1,000+
/night
Max price
Clear
Apply
Type
Cabin
Cottage
Mansion
House
Hotel
Villa
Boat
Condo
Show all
Clear
Apply
More filters
Create Alert
Vacation Rentals in Madison, CT
Sort by:
Relevance
Most relevant
Newest first
Price: low to high
Price: high to low
Sort by:
Relevance
Most relevant
Newest first
Price: low to high
Price: high to low
PRICE PER NIGHT
Up to $100
$100 - $199
From $200
ACCOMMODATION TYPES
Apartment
House
Condo
Top-Rated Vacation Rentals in Madison, CT
Book a vacation rental in Madison that has the highest visitor rating. Here are 6 of the best vacation rentals in Madison.
Price drop
Waterfront Estate Home - Beach and Shared Pool - East
10
Excellent
·
Details
Madison
·
9 br
·
Sleeps 20
·
More
Beach · Kitchen · Oven ·
More
From
$1,338
/night
Check availability
Property
House · 9 Beds · 6 baths
Amenities
Beach
Oven
Dishwasher
Swimming Pool
Furnished
Pool
Waterfront
Private Pool
Other spaces
Kitchen, Workspace
Price drop
Beautiful Beach Home and Garden Paradise
10
Excellent
·
Details
Madison
·
3 br
·
Sleeps 6
·
More
Wifi · Fitness Center · Air Conditioning ·
More
From
$470
/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Wifi
Fitness Center
Air Conditioning
Beach
Furnished
On Site Laundry
Oven
Dishwasher
Other spaces
Kitchen
Price drop
The River House South of Route 1 in Madison!
10
Excellent
·
Details
Madison
·
2 br
·
Sleeps 4
·
More
Furnished · Waterfront · Wifi ·
More
From
$499
/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Furnished
Waterfront
Wifi
Dishwasher
Air Conditioning
Oven
Ocean
On Site Laundry
Other spaces
Kitchen
Price drop
Steps from the beach! Perfect Shoreline Getaway
10
Excellent
·
Details
Madison
·
5 br
·
Sleeps 9
·
More
Furnished · Outdoor Space · Hot Tub ·
More
From
$560
/night
Check availability
Property
House · 5 Beds · 3 baths
Amenities
Furnished
Hot Tub
Oven
Air Conditioning
Wifi
Dishwasher
On Site Laundry
Other spaces
Kitchen
1.5 Acres Gorgeous 1860s Colonial House & Carriage Apartment
10
Excellent
·
Details
Madison
·
6 br
·
Sleeps 14
·
More
Oven · On Site Laundry · Fireplace ·
More
From
$953
/night
Check availability
Property
House · 6 Beds · 4 baths
Amenities
Oven
On Site Laundry
Fireplace
Beach
Wifi
Furnished
Dishwasher
Air Conditioning
Other spaces
Kitchen
Price drop
1860's Colonial House Near Downtown and Beaches!
10
Excellent
·
Details
Madison
·
4 br
·
Sleeps 10
·
More
Oven · Air Conditioning · On Site Laundry ·
More
From
$649
/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Oven
Air Conditioning
On Site Laundry
Fireplace
Beach
Furnished
Dishwasher
Wifi
Other spaces
Kitchen
Budget-Friendly Vacation Rentals in Madison, CT
Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Madison starting at $95. Use the price filter at the top of the page to search for more specific prices.
Cozy Summer Cottage in quiet Condo Community
10
Excellent
·
Details
Madison
·
1 br
·
Sleeps 2
·
More
Wifi · Furnished · Oven ·
More
From
$95
/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Wifi
Furnished
Oven
Beach
Air Conditioning
Other spaces
Kitchen
Price drop
Madison Beach House Just Steps To Private Beach On LI Sound At 7 Pent Rd
10
Excellent
·
Details
Madison
·
2 br
·
Sleeps 5
·
More
Outdoor Space · Kitchen · Oven ·
More
From
$100
/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Oven
Wifi
Residents Lounge
Air Conditioning
Beach
Fireplace
Furnished
Hot Tub
Other spaces
Kitchen
Price drop
Madison Beach House Just Steps To Private Beach On LI Sound at 11 Pent Rd
10
Excellent
·
Details
Madison
·
3 br
·
Sleeps 6
·
More
Oven · Beach · Outdoor Space ·
More
From
$105
/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Oven
Beach
Dishwasher
On Site Laundry
Ceiling Fan
Wifi
Air Conditioning
Residents Lounge
Other spaces
Kitchen
Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town
10
Excellent
·
Details
Madison
·
1 br
·
Sleeps 2
·
More
Fitness Center · Oven · On Site Laundry ·
More
From
$145
/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Fitness Center
Oven
On Site Laundry
Wifi
Residents Lounge
Wheelchair Accessible
Air Conditioning
Dishwasher
Other spaces
Workspace, Kitchen
Madison Beach Hotel, Curio Collection by Hilton
9.1
Excellent
·
Details
Madison
·
1 br
·
Sleeps 4
·
More
Ocean · Furnished · Dry Cleaning Service ·
More
From
$212
/night
Check availability
Property
Hotel · 1 Bed
Amenities
Ocean
Furnished
Dry Cleaning Service
On Site Laundry
Carpet
Fireplace
Beach
Wheelchair Accessible
Other spaces
Balcony, Workspace
Charming 2 bedroom cottage. Five minute walk to Private beach.
10
Excellent
·
Details
Madison
·
2 br
·
Sleeps 6
·
More
Furnished · On Site Laundry · Fitness Center ·
More
From
$255
/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Furnished
On Site Laundry
Fitness Center
Hardwood Floor
Wifi
Beach
Fireplace
Oven
Other spaces
Kitchen, Workspace, Deck
Expand your search criteria to see more vacation rentals near Madison.
Home
>
Connecticut Vacation Rentals
>
Madison Vacation Rentals
Updated: September 26, 2023
Nearby
Points of Interest
Bus stops
Cafes
Groceries
Nightlife
Parks
Rapid transit stations
Restaurants
Schools
Train stations
Clear
Apply
Search as I move the map