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Madison Vacation Rentals

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50 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

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

Direct waterfront renovated cottage.

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Classic Cottage With Water Views Of Long Island Sound--Monthly rates available!, vacation rental in Madison

Classic Cottage With Water Views Of Long Island Sound--Monthly rates available!

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Great Location! Middle Beach Road, vacation rental in Madison

Great Location! Middle Beach Road

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Brand New Listing Just 1 mile to Downtown and 1.5 miles to the Beach!, vacation rental in Madison

Brand New Listing Just 1 mile to Downtown and 1.5 miles to the Beach!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming summer home just steps from the beach!, vacation rental in Madison

Charming summer home just steps from the beach!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront beauty all year round. Enjoy a weekend getaway on Long Island Sound!, vacation rental in Madison

Waterfront beauty all year round. Enjoy a weekend getaway on Long Island Sound!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Wake up with Views of the Ocean, vacation rental in Madison

Wake up with Views of the Ocean

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Beachside studio vacation, vacation rental in Madison

Beachside studio vacation

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Newly Renovated Oceanfront Cottage On Joshua's Cove, Guilford CT, vacation rental in Madison

Newly Renovated Oceanfront Cottage On Joshua's Cove, Guilford CT

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach, vacation rental in Madison

Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Detached Home - Marina Guest House, vacation rental in Madison

Detached Home - Marina Guest House

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Beach House - Steps to private beach! Near outlets & casinos, sleeps 4, vacation rental in Madison

Charming Beach House - Steps to private beach! Near outlets & casinos, sleeps 4

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Beach House with Private Beach Access., vacation rental in Madison

Beautiful Beach House with Private Beach Access.

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Guilford Shoreline Cottage; Birder's Paradise, vacation rental in Madison

Guilford Shoreline Cottage; Birder's Paradise

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Seasonal cottage rental,waterview, vacation rental in Madison

Seasonal cottage rental,waterview

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Upscale Beach Home!!, vacation rental in Madison

Upscale Beach Home!!

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Family Friendly, Newly Renovated Cottage - Chalker Beach, vacation rental in Madison

Family Friendly, Newly Renovated Cottage - Chalker Beach

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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3 Bedroom House Westbrook, Connecticut, West Beach, vacation rental in Madison

3 Bedroom House Westbrook, Connecticut, West Beach

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Convenient CT Shoreline 3 Bedroom Ranch. Cozy Fireplace, walk to Beach, Sleeps 8, vacation rental in Madison

Convenient CT Shoreline 3 Bedroom Ranch. Cozy Fireplace, walk to Beach, Sleeps 8

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Branford-Pine Orchard Beach, vacation rental in Madison

Branford-Pine Orchard Beach

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Year Round Cottage, all you need.  Self Care, Social distance and Sunrises!, vacation rental in Madison

Cozy Year Round Cottage, all you need. Self Care, Social distance and Sunrises!

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Romantic Cottage by the Sea, steps to private beach, sleeps 2!, vacation rental in Madison

Romantic Cottage by the Sea, steps to private beach, sleeps 2!

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Relaxing summer rental, walking distance to the beach, short ride to the outlets, vacation rental in Madison

Relaxing summer rental, walking distance to the beach, short ride to the outlets

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Pristine Water-view Beach Home - Steps away from the beach, vacation rental in Madison

Pristine Water-view Beach Home - Steps away from the beach

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cozy cottage near Clinton Marina on CT Shoreline, vacation rental in Madison

Cozy cottage near Clinton Marina on CT Shoreline

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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3+BR/ 2 bath in Exclusive Grove Beach Association Community... Central AC, vacation rental in Madison

3+BR/ 2 bath in Exclusive Grove Beach Association Community... Central AC

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Great family home, big back yard with grill and fire pit., vacation rental in Madison

Great family home, big back yard with grill and fire pit.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy home with ocean views in private beach community Off season rates now!, vacation rental in Madison

Cozy home with ocean views in private beach community Off season rates now!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful views from private deck. Overlooking the Hammock  River Marsh wildlife, vacation rental in Madison

Beautiful views from private deck. Overlooking the Hammock River Marsh wildlife

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Remodeled Clinton 2 BR/1 Bath Shore Cottage, Walk To Private Beach, vacation rental in Madison

Remodeled Clinton 2 BR/1 Bath Shore Cottage, Walk To Private Beach

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Adorable large beach cottage, vacation rental in Madison

Adorable large beach cottage

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous Designer Contemporary Beach House with Views, vacation rental in Madison

Gorgeous Designer Contemporary Beach House with Views

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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11 Bedroom Home on Pot Island for Family,  Re-Unions, Retreats, vacation rental in Madison

11 Bedroom Home on Pot Island for Family, Re-Unions, Retreats

11 bedrooms
6 bathrooms
Sleeps 22
Match: Sleeps
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Two bedroom house with private beach and club within walking distance, vacation rental in Madison

Two bedroom house with private beach and club within walking distance

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Heaven is a Little Beach House!, vacation rental in Madison

Heaven is a Little Beach House!

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Ennis Cottage- A Seaside Getaway!, vacation rental in Madison

Ennis Cottage- A Seaside Getaway!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Steps to beach 4bd 2 bth Sleeps 13, vacation rental in Madison

Steps to beach 4bd 2 bth Sleeps 13

3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Waterfront cottage on Long Island Sound with awesome Salt Island out front, vacation rental in Madison

Waterfront cottage on Long Island Sound with awesome Salt Island out front

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Quaint CT Shore Cottage - Ocean View, vacation rental in Madison

Quaint CT Shore Cottage - Ocean View

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lovely Connecticut Beach Community Home -Upgraded,Sleeps 11, vacation rental in Madison

Lovely Connecticut Beach Community Home -Upgraded,Sleeps 11

4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Private luxury waterfront home, vacation rental in Madison

Private luxury waterfront home

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Amazing Waterfront Home, Private Beach,Hot Tub + Tennis/Beach Club, vacation rental in Madison

Amazing Waterfront Home, Private Beach,Hot Tub + Tennis/Beach Club

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Peace Barn in the heart of the CT River Valley, vacation rental in Madison

Peace Barn in the heart of the CT River Valley

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Pet-Friendly Branford Home - 10Min Walk to Beach!, vacation rental in Madison

Pet-Friendly Branford Home - 10Min Walk to Beach!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Life's at ease, with an ocean breeze!, vacation rental in Madison

Life's at ease, with an ocean breeze!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Money Island Home w/Deck, Kayak, Paddleboards, vacation rental in Madison

Money Island Home w/Deck, Kayak, Paddleboards

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Waterfront New Haven Area Apt. on Joshua Cove, vacation rental in Madison

Waterfront New Haven Area Apt. on Joshua Cove

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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AIR-CONDITIONED Gorgeous Newly Renovated Home with an Oceanview and Beach Access, vacation rental in Madison

AIR-CONDITIONED Gorgeous Newly Renovated Home with an Oceanview and Beach Access

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW LISTING Relaxing marsh view pristine beach house, 3 bedrooms 2 baths, vacation rental in Madison

NEW LISTING Relaxing marsh view pristine beach house, 3 bedrooms 2 baths

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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