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Madison Holiday Rentals

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

Direct waterfront renovated cottage.

4 bedrooms
4 bathrooms
Sleeps 8
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Classic Cottage With Water Views Of Long Island Sound--Monthly rates available!, holiday 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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2 bedroom Apartment Brand New Listing Close to Beach & Downtown!, holiday rental in Madison

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

3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming summer home just steps from the beach!, holiday 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!, holiday 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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Beachside studio vacation, holiday rental in Madison

Beachside studio vacation

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Wake up with Views of the Ocean, holiday rental in Madison

Wake up with Views of the Ocean

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Newly Renovated Oceanfront Cottage On Joshua's Cove, Guilford CT, holiday 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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Family Friendly, Newly Renovated Cottage - Chalker Beach, holiday rental in Madison

Family Friendly, Newly Renovated Cottage - Chalker Beach

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Beach House with Private Beach Access., holiday rental in Madison

Beautiful Beach House with Private Beach Access.

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Year Round Cottage, all you need.  Self Care, Social distance and Sunrises!, holiday 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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Charming Beach House - Steps to private beach! Near outlets & casinos, sleeps 4, holiday rental in Madison

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

2 bedrooms
1 bathroom
Sleeps 4
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Cozy cottage near Clinton Marina on CT Shoreline, holiday rental in Madison

Cozy cottage near Clinton Marina on CT Shoreline

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Seasonal cottage rental,waterview, holiday rental in Madison

Seasonal cottage rental,waterview

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Convenient CT Shoreline 3 Bedroom Ranch. Cozy Fireplace, walk to Beach, Sleeps 8, holiday rental in Madison

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

3 bedrooms
2 bathrooms
Sleeps 8
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3 Bedroom House Westbrook, Connecticut, West Beach, holiday rental in Madison

3 Bedroom House Westbrook, Connecticut, West Beach

3 bedrooms
1 bathroom
Sleeps 8
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Upscale Beach Home!!, holiday rental in Madison

Upscale Beach Home!!

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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3+BR/ 2 bath in Exclusive Grove Beach Association Community... Central AC, holiday rental in Madison

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

3 bedrooms
2 bathrooms
Sleeps 7
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Relaxing summer rental, walking distance to the beach, short ride to the outlets, holiday 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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Great family home, big back yard with grill and fire pit., holiday rental in Madison

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

3 bedrooms
2 bathrooms
Sleeps 6
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Branford-Pine Orchard Beach, holiday rental in Madison

Branford-Pine Orchard Beach

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Romantic Cottage by the Sea, steps to private beach, sleeps 2!, holiday 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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Pristine Water-view Beach Home - Steps away from the beach, holiday 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 home with ocean views in private beach community Off season rates now!, holiday 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, holiday 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, holiday rental in Madison

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

2 bedrooms
1 bathroom
Sleeps 5
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Adorable large beach cottage, holiday 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, holiday rental in Madison

Gorgeous Designer Contemporary Beach House with Views

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Two bedroom house with private beach and club within walking distance, holiday 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!, holiday 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!, holiday 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, holiday rental in Madison

Steps to beach 4bd 2 bth Sleeps 13

3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Waterfront Relaxation!, holiday rental in Madison

Waterfront Relaxation!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront cottage on Long Island Sound with awesome Salt Island out front, holiday 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, holiday rental in Madison

Quaint CT Shore Cottage - Ocean View

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private luxury waterfront home, holiday rental in Madison

Private luxury waterfront home

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Rustic Retreat near Bill Miller’s Castle available June 29th!!, holiday rental in Madison

Rustic Retreat near Bill Miller’s Castle available June 29th!!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Welcome to Cornfield Coop, holiday rental in Madison

Welcome to Cornfield Coop

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Amazing Waterfront Home, Private Beach,Hot Tub + Tennis/Beach Club, holiday 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, holiday 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!, holiday 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!, holiday 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, holiday rental in Madison

Money Island Home w/Deck, Kayak, Paddleboards

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Saybrook Manor House, Walk to Cove Beach!, holiday rental in Madison

Saybrook Manor House, Walk to Cove Beach!

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

Waterfront New Haven Area Apt. on Joshua Cove

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Time to book your beach vacation for Summer 2020!, holiday rental in Madison

Time to book your beach vacation for Summer 2020!

5 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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NEW! Historic Home w/ Large Yard Near Dwtn Essex!, holiday rental in Madison

NEW! Historic Home w/ Large Yard Near Dwtn Essex!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The perfect family beach house, holiday rental in Madison

The perfect family beach house

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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4BR Directly on the Beach Bring the Family and Start making memories, holiday rental in Madison

4BR Directly on the Beach Bring the Family and Start making memories

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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