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Madison Vacation Rentals

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39 rentals in Madison.
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Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town, vacation rental in Madison
Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town, vacation rental in Madison
Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town, vacation rental in Madison

Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Direct waterfront renovated cottage., vacation rental in Madison
Direct waterfront renovated cottage., vacation rental in Madison
Direct waterfront renovated cottage., vacation rental in Madison

Direct waterfront renovated cottage.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Madison Beach House Just Steps To Private Beach On LI Sound At 7 Pent Rd, vacation rental in Madison
Madison Beach House Just Steps To Private Beach On LI Sound At 7 Pent Rd, vacation rental in Madison
Madison Beach House Just Steps To Private Beach On LI Sound At 7 Pent Rd, vacation rental in Madison

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Gorgeous, modern waterfront luxury home in Madison, CT, vacation rental in Madison
Gorgeous, modern waterfront luxury home in Madison, CT, vacation rental in Madison
Gorgeous, modern waterfront luxury home in Madison, CT, vacation rental in Madison

Gorgeous, modern waterfront luxury home in Madison, CT

Rental Home
4 bedrooms
5 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront Estate Home - Beach and Shared Pool East, vacation rental in Madison
Waterfront Estate Home - Beach and Shared Pool East, vacation rental in Madison
Waterfront Estate Home - Beach and Shared Pool East, vacation rental in Madison

Waterfront Estate Home - Beach and Shared Pool East

Rental Home
9 bedrooms
6 bathrooms
Sleeps 20
Match: Sleeps
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Classic Updated Beachfront Beauty with Stunning Waterviews and Private Beach, vacation rental in Madison
Classic Updated Beachfront Beauty with Stunning Waterviews and Private Beach, vacation rental in Madison
Classic Updated Beachfront Beauty with Stunning Waterviews and Private Beach, vacation rental in Madison

Classic Updated Beachfront Beauty with Stunning Waterviews and Private Beach

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Ideal Madison Beach House, vacation rental in Madison
Ideal Madison Beach House, vacation rental in Madison
Ideal Madison Beach House, vacation rental in Madison

Ideal Madison Beach House

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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4 bedroom Home- steps to sandy beach and walk to town, vacation rental in Madison
4 bedroom Home- steps to sandy beach and walk to town, vacation rental in Madison
4 bedroom Home- steps to sandy beach and walk to town, vacation rental in Madison

4 bedroom Home- steps to sandy beach and walk to town

Rental Home
4 bedrooms
5 bathrooms
Sleeps 4
Match: Sleeps
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Newly Renovated Carriage House Near Town & Beaches!, vacation rental in Madison
Newly Renovated Carriage House Near Town & Beaches!, vacation rental in Madison
Newly Renovated Carriage House Near Town & Beaches!, vacation rental in Madison

Newly Renovated Carriage House Near Town & Beaches!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Madison Beach House Just Steps To Private Beach On LI Sound at 11 Pent Rd, vacation rental in Madison
Madison Beach House Just Steps To Private Beach On LI Sound at 11 Pent Rd, vacation rental in Madison
Madison Beach House Just Steps To Private Beach On LI Sound at 11 Pent Rd, vacation rental in Madison

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Family house near Hammonasset beach state park, vacation rental in Madison
Family house near Hammonasset beach state park, vacation rental in Madison
Family house near Hammonasset beach state park, vacation rental in Madison

Family house near Hammonasset beach state park

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Classic Family Beach Cottage!, vacation rental in Madison
Classic Family Beach Cottage!, vacation rental in Madison
Classic Family Beach Cottage!, vacation rental in Madison

Classic Family Beach Cottage!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Madison, CT - Coastal Modern Farmhouse w/Outdoor Kitchen & Large Fenced in Patio, vacation rental in Madison
Madison, CT - Coastal Modern Farmhouse w/Outdoor Kitchen & Large Fenced in Patio, vacation rental in Madison
Madison, CT - Coastal Modern Farmhouse w/Outdoor Kitchen & Large Fenced in Patio, vacation rental in Madison

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

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Adorable Cottage close to Beaches and Town, vacation rental in Madison
Adorable Cottage close to Beaches and Town, vacation rental in Madison
Adorable Cottage close to Beaches and Town, vacation rental in Madison

Adorable Cottage close to Beaches and Town

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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1860's Colonial House Near Downtown and Beaches!, vacation rental in Madison
1860's Colonial House Near Downtown and Beaches!, vacation rental in Madison
1860's Colonial House Near Downtown and Beaches!, vacation rental in Madison

1860's Colonial House Near Downtown and Beaches!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Estate Home-Beach and Shared Pool - West, vacation rental in Madison
Waterfront Estate Home-Beach and Shared Pool - West, vacation rental in Madison
Waterfront Estate Home-Beach and Shared Pool - West, vacation rental in Madison

Waterfront Estate Home-Beach and Shared Pool - West

Rental Home
9 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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2 bedroom Apartment Brand New Listing Close to Beach & Downtown!, vacation rental in Madison
2 bedroom Apartment Brand New Listing Close to Beach & Downtown!, vacation rental in Madison
2 bedroom Apartment Brand New Listing Close to Beach & Downtown!, vacation rental in Madison

2 bedroom Apartment Brand New Listing Close to Beach & Downtown!

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Beach Home and Garden Paradise, vacation rental in Madison
Beautiful Beach Home and Garden Paradise, vacation rental in Madison
Beautiful Beach Home and Garden Paradise, vacation rental in Madison

Beautiful Beach Home and Garden Paradise

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Sundrenched 5 BR Home w/ Private Dock Near Beaches, vacation rental in Madison
Sundrenched 5 BR Home w/ Private Dock Near Beaches, vacation rental in Madison
Sundrenched 5 BR Home w/ Private Dock Near Beaches, vacation rental in Madison

Sundrenched 5 BR Home w/ Private Dock Near Beaches

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Lovely Cottage By The Beach With Spectacular Views Of The Long Island Sound, vacation rental in Madison
Lovely Cottage By The Beach With Spectacular Views Of The Long Island Sound, vacation rental in Madison
Lovely Cottage By The Beach With Spectacular Views Of The Long Island Sound, vacation rental in Madison

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
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Classic shoreline cottage , Madison CT private beach, vacation rental in Madison
Classic shoreline cottage , Madison CT private beach, vacation rental in Madison
Classic shoreline cottage , Madison CT private beach, vacation rental in Madison

Classic shoreline cottage , Madison CT private beach

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming summer home just steps from the beach!, vacation rental in Madison
Charming summer home just steps from the beach!, vacation rental in Madison
Charming summer home just steps from the beach!, vacation rental in Madison

Charming summer home just steps from the beach!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Steps to beach; walk to town, vacation rental in Madison
Steps to beach; walk to town, vacation rental in Madison
Steps to beach; walk to town, vacation rental in Madison

Steps to beach; walk to town

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Private Beachfront House in Madison CT - Sleeps 8 - Rare, vacation rental in Madison
Private Beachfront House in Madison CT - Sleeps 8 - Rare, vacation rental in Madison
Private Beachfront House in Madison CT - Sleeps 8 - Rare, vacation rental in Madison

Private Beachfront House in Madison CT - Sleeps 8 - Rare

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beach Cottage available, vacation rental in Madison
Beach Cottage available, vacation rental in Madison
Beach Cottage available, vacation rental in Madison

Beach Cottage available

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Great 3BD/2BA Sunny Ranch with Private Beach and Large Yard, vacation rental in Madison
Great 3BD/2BA Sunny Ranch with Private Beach and Large Yard, vacation rental in Madison
Great 3BD/2BA Sunny Ranch with Private Beach and Large Yard, vacation rental in Madison

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Madison Beach Cottage newly renovated w/beach access, vacation rental in Madison
Madison Beach Cottage newly renovated w/beach access, vacation rental in Madison
Madison Beach Cottage newly renovated w/beach access, vacation rental in Madison

Madison Beach Cottage newly renovated w/beach access

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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NEW! SEAVIEW COTTAGE at THE OCEAN, vacation rental in Madison
NEW! SEAVIEW COTTAGE at THE OCEAN, vacation rental in Madison
NEW! SEAVIEW COTTAGE at THE OCEAN, vacation rental in Madison

NEW! SEAVIEW COTTAGE at THE OCEAN

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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New luxury beach house, vacation rental in Madison
New luxury beach house, vacation rental in Madison
New luxury beach house, vacation rental in Madison

New luxury beach house

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Madison, CT - Coastal Modern House w/ Private Beach & Large Fenced in Backyard, vacation rental in Madison
Madison, CT - Coastal Modern House w/ Private Beach & Large Fenced in Backyard, vacation rental in Madison
Madison, CT - Coastal Modern House w/ Private Beach & Large Fenced in Backyard, vacation rental in Madison

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Historic Madison Home on lovely 1.2 acre setting and 5 minutes from the beach., vacation rental in Madison
Historic Madison Home on lovely 1.2 acre setting and 5 minutes from the beach., vacation rental in Madison
Historic Madison Home on lovely 1.2 acre setting and 5 minutes from the beach., vacation rental in Madison

Historic Madison Home on lovely 1.2 acre setting and 5 minutes from the beach.

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Cozy Summer Cottage in quiet Condo Community, vacation rental in Madison
Cozy Summer Cottage in quiet Condo Community, vacation rental in Madison
Cozy Summer Cottage in quiet Condo Community, vacation rental in Madison

Cozy Summer Cottage in quiet Condo Community

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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1 Block from Water - Welcoming 4 Bedroom Home, vacation rental in Madison
1 Block from Water - Welcoming 4 Bedroom Home, vacation rental in Madison
1 Block from Water - Welcoming 4 Bedroom Home, vacation rental in Madison

1 Block from Water - Welcoming 4 Bedroom Home

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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renovated 2 bedroom cozy apartment, vacation rental in Madison
renovated 2 bedroom cozy apartment, vacation rental in Madison
renovated 2 bedroom cozy apartment, vacation rental in Madison

renovated 2 bedroom cozy apartment

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Summer Getaway - Monthly Rental, vacation rental in Madison
Summer Getaway - Monthly Rental, vacation rental in Madison
Summer Getaway - Monthly Rental, vacation rental in Madison

Summer Getaway - Monthly Rental

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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1.5 Acres Gorgeous 1860s Colonial House & Carriage Apartment, vacation rental in Madison
1.5 Acres Gorgeous 1860s Colonial House & Carriage Apartment, vacation rental in Madison
1.5 Acres Gorgeous 1860s Colonial House & Carriage Apartment, vacation rental in Madison

1.5 Acres Gorgeous 1860s Colonial House & Carriage Apartment

Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Downtown home - walk to stores, restaurants, beaches, golf, and train station., vacation rental in Madison
Downtown home - walk to stores, restaurants, beaches, golf, and train station., vacation rental in Madison
Downtown home - walk to stores, restaurants, beaches, golf, and train station., vacation rental in Madison

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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7 Min Walk from Water: Cheerful 4 Bedroom Home, vacation rental in Madison
7 Min Walk from Water: Cheerful 4 Bedroom Home, vacation rental in Madison
7 Min Walk from Water: Cheerful 4 Bedroom Home, vacation rental in Madison

7 Min Walk from Water: Cheerful 4 Bedroom Home

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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NEW! Charming Madison Retreat ~ 3 Mi to Beaches!, vacation rental in Madison
NEW! Charming Madison Retreat ~ 3 Mi to Beaches!, vacation rental in Madison
NEW! Charming Madison Retreat ~ 3 Mi to Beaches!, vacation rental in Madison

NEW! Charming Madison Retreat ~ 3 Mi to Beaches!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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