Madison, Connecticut

Vacation Rentals in Madison, Connecticut

Discover 56 vacation rental properties in Madison. From 1 to 9 bedrooms. Average $519/night. 100% have pools.

56 verified listings Book securely on VRBO Prices updated March 2026

56 properties available

Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!

Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!

2 beds 1 bath
PoolA/CWiFiBalcony
$390/night
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Madison Beach House Just Steps To Private Beach On LI Sound at 11 Pent Rd

Madison Beach House Just Steps To Private Beach On LI Sound at 11 Pent Rd

3 beds 2 baths
PoolA/CWiFiBalcony
$276/night
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Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town

Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town

1 bed 1 bath
PoolA/CWiFiBalcony
$157/night
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Beachfront cottage on Historic Circle Beach

Beachfront cottage on Historic Circle Beach

6 beds 3 baths
PoolA/CWiFiBalcony
$500/night
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Direct waterfront renovated cottage.

Direct waterfront renovated cottage.

4 beds 2 baths
PoolA/CWiFiBalcony
$636/night
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Newly Renovated Carriage House Near Town & Beaches!

Newly Renovated Carriage House Near Town & Beaches!

2 beds 1 bath
PoolA/CWiFiBalcony
$451/night
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Quintessential New England shoreline charm, just steps to private beach

Quintessential New England shoreline charm, just steps to private beach

3 beds 1 bath
PoolA/CWiFiBalcony
$447/night
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Newly renovated cottage in a private beach community.

Newly renovated cottage in a private beach community.

3 beds 1 bath
PoolA/CWiFiBalcony
$351/night
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Madison Beach House Just Steps To Private Beach On LI Sound At 7 Pent Rd

Madison Beach House Just Steps To Private Beach On LI Sound At 7 Pent Rd

2 beds 1 bath
PoolA/CWiFiBalcony
$204/night
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Beautiful Beach Home and Garden Paradise

Beautiful Beach Home and Garden Paradise

3 beds 2 baths
PoolA/CWiFiBalcony
$701/night
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Madison, CT - Coastal Modern Farmhouse w/Outdoor Kitchen & Large Fenced in Patio

Madison, CT - Coastal Modern Farmhouse w/Outdoor Kitchen & Large Fenced in Patio

3 beds 1 bath
PoolA/CWiFiBalcony
$405/night
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New Madison beach house - Ocean front- Great views- booking Summer 2024

New Madison beach house - Ocean front- Great views- booking Summer 2024

4 beds 2 baths
PoolA/CWiFiBalcony
$759/night
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Beachfront home with heated pool

Beachfront home with heated pool

3 beds 3 baths
PoolA/CWiFiBalcony
$1,001/night
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Immaculate Year Round Cottage Steps from the Beach Sleeps 6

Immaculate Year Round Cottage Steps from the Beach Sleeps 6

2 beds 1 bath
PoolA/CWiFiBalcony
$381/night
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Ideal Madison home just steps to the beach

Ideal Madison home just steps to the beach

4 beds 2 baths
PoolA/CWiFiBalcony
$726/night
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Classic Updated Beachfront Beauty with Stunning Waterviews and Private Beach

Classic Updated Beachfront Beauty with Stunning Waterviews and Private Beach

5 beds 3 baths
PoolA/CWiFiBalcony
$532/night
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Adorable Cottage close to Beaches and Town

Adorable Cottage close to Beaches and Town

2 beds 1 bath
PoolA/CWiFiBalcony
$296/night
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Waterfront Estate Home - Beach and Shared Pool - East

Waterfront Estate Home - Beach and Shared Pool - East

9 beds 3 baths
PoolA/CWiFiBalcony
$1,090/night
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Vacation near Beaches and Town

Vacation near Beaches and Town

4 beds 2 baths
PoolA/CWiFiBalcony
$475/night
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Contemporary and Stylish, 4-Bedroom, Madison CT

Contemporary and Stylish, 4-Bedroom, Madison CT

4 beds 2 baths
PoolA/CWiFiBalcony
$357/night
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Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!

Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!

5 beds 4 baths
PoolA/CWiFiBalcony
$382/night
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1860's Colonial House Near Downtown and Beaches!

1860's Colonial House Near Downtown and Beaches!

4 beds 3 baths
PoolA/CWiFiBalcony
$716/night
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1.5 Acres Gorgeous 1860s Colonial House & Carriage Apartment

1.5 Acres Gorgeous 1860s Colonial House & Carriage Apartment

6 beds 4 baths
PoolA/CWiFiBalcony
$1,134/night
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5 min from 4 beaches & town! - hot tub, jacuzzi bath, bar/movie room

5 min from 4 beaches & town! - hot tub, jacuzzi bath, bar/movie room

3 beds 2 baths
PoolA/CWiFiBalcony
$240/night
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Cozy Summer Cottage in quiet Condo Community

Cozy Summer Cottage in quiet Condo Community

1 bed 1 bath
PoolA/CWiFiBalcony
$95/night
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Cozy Family Beach Cottage

Cozy Family Beach Cottage

5 beds 1 bath
PoolA/CWiFiBalcony
$400/night
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Madison, CT - Coastal Modern House w/ Private Beach & Large Fenced in Backyard

Madison, CT - Coastal Modern House w/ Private Beach & Large Fenced in Backyard

3 beds 2 baths
PoolA/CWiFiBalcony
$348/night
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Downtown home - walk to stores, restaurants, beaches, golf, and train station.

Downtown home - walk to stores, restaurants, beaches, golf, and train station.

4 beds 3 baths
PoolA/CWiFiBalcony
$645/night
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Charming 2 bedroom Beach House. Ten minute walk to Private beach.

Charming 2 bedroom Beach House. Ten minute walk to Private beach.

2 beds 1 bath
PoolA/CWiFiBalcony
$271/night
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Fun and Relaxing Madison Game Room Retreat

Fun and Relaxing Madison Game Room Retreat

4 beds 2 baths
PoolA/CWiFiBalcony
$433/night
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Steps from the beach! Perfect Shoreline Getaway

Steps from the beach! Perfect Shoreline Getaway

5 beds 2 baths
PoolA/CWiFiBalcony
$801/night
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Coastal getaway with water views in every room

Coastal getaway with water views in every room

3 beds 1 bath
PoolA/CWiFiBalcony
$751/night
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Classic shoreline cottage 5-minute walk to the beach, Madison CT private beach

Classic shoreline cottage 5-minute walk to the beach, Madison CT private beach

4 beds 2 baths
PoolA/CWiFiBalcony
$400/night
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7 Min Walk from Water: Cheerful 4 Bedroom Home

7 Min Walk from Water: Cheerful 4 Bedroom Home

4 beds 3 baths
PoolA/CWiFiBalcony
$400/night
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Secluded Family Friendly Beach House

Secluded Family Friendly Beach House

4 beds 1 bath
PoolA/CWiFiBalcony
$367/night
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Oceanview Cottage by East Wharf Beach Madison CT

Oceanview Cottage by East Wharf Beach Madison CT

6 beds 3 baths
PoolA/CWiFiBalcony
$851/night
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Special winter rates CT home close to beaches, parks, hikes, local skiing

Special winter rates CT home close to beaches, parks, hikes, local skiing

5 beds 3 baths
PoolA/CWiFiBalcony
$726/night
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Chill and relax. Or remote to work from the beach.

Chill and relax. Or remote to work from the beach.

3 beds 1 bath
PoolA/CWiFiBalcony
$583/night
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Great 3BD/2BA Sunny Ranch with Private Beach and Large Yard

Great 3BD/2BA Sunny Ranch with Private Beach and Large Yard

3 beds 2 baths
PoolA/CWiFiBalcony
$400/night
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Lovely Cottage By The Beach With Spectacular Views Of The Long Island Sound

Lovely Cottage By The Beach With Spectacular Views Of The Long Island Sound

4 beds 2 baths
PoolA/CWiFiBalcony
$551/night
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Ideal Madison vacation home just steps to private beach!

Ideal Madison vacation home just steps to private beach!

3 beds 2 baths
PoolA/CWiFiBalcony
$601/night
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Family-friendly cottage in a quiet neighborhood

Family-friendly cottage in a quiet neighborhood

5 beds 1 bath
PoolA/CWiFiBalcony
$340/night
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New Availability! Private Beachfront House in Madison CT - Sleeps 8 - Rare

New Availability! Private Beachfront House in Madison CT - Sleeps 8 - Rare

4 beds 3 baths
PoolA/CWiFiBalcony
$1,201/night
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Steps to beach; walk to town - premium weeks still available!

Steps to beach; walk to town - premium weeks still available!

4 beds 3 baths
PoolA/CWiFiBalcony
$601/night
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Charming cottage for a beach getaway in the beautiful town of Madison, CT.

Charming cottage for a beach getaway in the beautiful town of Madison, CT.

2 beds 1 bath
PoolA/CWiFiBalcony
$315/night
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renovated 2 bedroom cozy apartment

renovated 2 bedroom cozy apartment

2 beds 1 bath
PoolA/CWiFiBalcony
$300/night
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Available July 1, 2024 2 week or monthly July /August

Available July 1, 2024 2 week or monthly July /August

2 beds 1 bath
PoolA/CWiFiBalcony
Price on request
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1 Block from Water - Welcoming 4 Bedroom Home

1 Block from Water - Welcoming 4 Bedroom Home

4 beds 2 baths
PoolA/CWiFiBalcony
$584/night
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