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Old Saybrook Holiday Rentals

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50 rentals in Old Saybrook.
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Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach, holiday rental in Old Saybrook

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

2 bedrooms
1 bathroom
Sleeps 6
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Family Friendly, Newly Renovated Cottage - Chalker Beach, holiday rental in Old Saybrook

Family Friendly, Newly Renovated Cottage - Chalker Beach

3 bedrooms
3 bathrooms
Sleeps 6
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Saybrook Point Cottage  - Charming and Private, holiday rental in Old Saybrook

Saybrook Point Cottage - Charming and Private

1 bedroom
1 bathroom
Sleeps 2
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adorable ranch in beach community, holiday rental in Old Saybrook

adorable ranch in beach community

3 bedrooms
1 bathroom
Sleeps 6
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Convenience and Privacy in Exclusive North Cove!  Close to beaches and downtown!, holiday rental in Old Saybrook

Convenience and Privacy in Exclusive North Cove! Close to beaches and downtown!

3 bedrooms
2 bathrooms
Sleeps 8
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The Osprey - South Cove, Old Saybrook, CT - water views & close to town., holiday rental in Old Saybrook

The Osprey - South Cove, Old Saybrook, CT - water views & close to town.

1 bedroom
1 bathroom
Sleeps 4
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Great family home, big back yard with grill and fire pit., holiday rental in Old Saybrook

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

3 bedrooms
2 bathrooms
Sleeps 6
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SeaStar Beach House -Knollwood Private beach association, holiday rental in Old Saybrook

SeaStar Beach House -Knollwood Private beach association

4 bedrooms
1 bathroom
Sleeps 6
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Inquire about winter rates Jan Feb March, holiday rental in Old Saybrook

Inquire about winter rates Jan Feb March

3 bedrooms
2 bathrooms
Sleeps 8
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Waterfront Relaxation!, holiday rental in Old Saybrook

Waterfront Relaxation!

3 bedrooms
1 bathroom
Sleeps 6
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Time to book your beach vacation for Summer 2020!, holiday rental in Old Saybrook

Time to book your beach vacation for Summer 2020!

5 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Saybrook Manor House, Walk to Cove Beach!, holiday rental in Old Saybrook

Saybrook Manor House, Walk to Cove Beach!

3 bedrooms
1 bathroom
Sleeps 8
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Welcome to Cornfield Coop, holiday rental in Old Saybrook

Welcome to Cornfield Coop

3 bedrooms
2 bathrooms
Sleeps 8
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Waterfront beauty all year round. Enjoy a weekend getaway on Long Island Sound!, holiday rental in Old Saybrook

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

3 bedrooms
2 bathrooms
Sleeps 6
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Beautiful getaway cape by the lake, holiday rental in Old Saybrook

Beautiful getaway cape by the lake

3 bedrooms
3 bathrooms
Sleeps 8
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Wake up with Views of the Ocean, holiday rental in Old Saybrook

Wake up with Views of the Ocean

2 bedrooms
2 bathrooms
Sleeps 7
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Seasonal cottage rental,waterview, holiday rental in Old Saybrook

Seasonal cottage rental,waterview

3 bedrooms
1 bathroom
Sleeps 6
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Cozy Year Round Cottage, all you need.  Self Care, Social distance and Sunrises!, holiday rental in Old Saybrook

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

3 bedrooms
3 bathrooms
Sleeps 7
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Upscale Beach Home!!, holiday rental in Old Saybrook

Upscale Beach Home!!

4 bedrooms
4 bathrooms
Sleeps 10
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3 Bedroom House Westbrook, Connecticut, West Beach, holiday rental in Old Saybrook

3 Bedroom House Westbrook, Connecticut, West Beach

3 bedrooms
1 bathroom
Sleeps 8
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Convenient CT Shoreline 3 Bedroom Ranch. Cozy Fireplace, walk to Beach, Sleeps 8, holiday rental in Old Saybrook

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

3 bedrooms
2 bathrooms
Sleeps 8
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Steps from private beach, screened-in wraparound porch, water views., holiday rental in Old Saybrook

Steps from private beach, screened-in wraparound porch, water views.

4 bedrooms
3 bathrooms
Sleeps 7
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Relaxing summer rental, walking distance to the beach, short ride to the outlets, holiday rental in Old Saybrook

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

3 bedrooms
1 bathroom
Sleeps 6
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Pristine Water-view Beach Home - Steps away from the beach, holiday rental in Old Saybrook

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

4 bedrooms
3 bathrooms
Sleeps 8
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Make Memories in Charming Hawk's Nest Beach!, holiday rental in Old Saybrook

Make Memories in Charming Hawk's Nest Beach!

3 bedrooms
1 bathroom
Sleeps 6
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Classic Waterfront Cottage at Hawks Nest Beach, holiday rental in Old Saybrook

Classic Waterfront Cottage at Hawks Nest Beach

4 bedrooms
3 bathrooms
Sleeps 9
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Cozy home with ocean views in private beach community Off season rates now!, holiday rental in Old Saybrook

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

2 bedrooms
2 bathrooms
Sleeps 6
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Family Activities All Summer Long....40 Steps to the Ocean!, holiday rental in Old Saybrook

Family Activities All Summer Long....40 Steps to the Ocean!

3 bedrooms
1 bathroom
Sleeps 6
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Adorable large beach cottage, holiday rental in Old Saybrook

Adorable large beach cottage

4 bedrooms
2 bathrooms
Sleeps 8
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Oceanfront Charming Cottage on Hawk's Nest, holiday rental in Old Saybrook

Oceanfront Charming Cottage on Hawk's Nest

3 bedrooms
2 bathrooms
Sleeps 8
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Family Beach Cottage, holiday rental in Old Saybrook

Family Beach Cottage

3 bedrooms
1 bathroom
Sleeps 6
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Old Lyme Hawks Nest Beach, Old Lyme, holiday rental in Old Saybrook

Old Lyme Hawks Nest Beach, Old Lyme

3 bedrooms
3 bathrooms
Sleeps 8
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Weekly Summer Beach Rental, holiday rental in Old Saybrook

Weekly Summer Beach Rental

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Heaven is a Little Beach House!, holiday rental in Old Saybrook

Heaven is a Little Beach House!

3 bedrooms
2 bathrooms
Sleeps 5
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Newly Remodeled Condo-3 Bedroom/1 Bath/ Sleeps 6, holiday rental in Old Saybrook

Newly Remodeled Condo-3 Bedroom/1 Bath/ Sleeps 6

3 bedrooms
1 bathroom
Sleeps 6
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Condo-Sleeps 6-Steps from the Beach, holiday rental in Old Saybrook

Condo-Sleeps 6-Steps from the Beach

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Modern Beachfront Condo, holiday rental in Old Saybrook

Modern Beachfront Condo

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Quaint Coastal Cottage in Beautiful White Sands Beach, holiday rental in Old Saybrook

Quaint Coastal Cottage in Beautiful White Sands Beach

4 bedrooms
2 bathrooms
Sleeps 8
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Stay just steps away from a beautiful private beach in Old Lyme!, holiday rental in Old Saybrook

Stay just steps away from a beautiful private beach in Old Lyme!

2 bedrooms
1 bathroom
Sleeps 6
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Waterfront cottage on Long Island Sound with awesome Salt Island out front, holiday rental in Old Saybrook

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

4 bedrooms
3 bathrooms
Sleeps 8
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Fabulous private gated estate in Old Lyme CT with breathtaking views, holiday rental in Old Saybrook

Fabulous private gated estate in Old Lyme CT with breathtaking views

3 bedrooms
4 bathrooms
Sleeps 8
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Quaint CT Shore Cottage - Ocean View, holiday rental in Old Saybrook

Quaint CT Shore Cottage - Ocean View

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Beach Cottage, holiday rental in Old Saybrook

Charming Beach Cottage

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lovely Connecticut Beach Community Home -Upgraded,Sleeps 11, holiday rental in Old Saybrook

Lovely Connecticut Beach Community Home -Upgraded,Sleeps 11

4 bedrooms
2 bathrooms
Sleeps 11
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Classic Cottage in Best Private Community in Old Lyme CT., holiday rental in Old Saybrook

Classic Cottage in Best Private Community in Old Lyme CT.

3 bedrooms
1 bathroom
Sleeps 6
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Luxurious living on a bucolic alpaca farm, holiday rental in Old Saybrook

Luxurious living on a bucolic alpaca farm

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Coastal Connecticut Apt: Walk to Sound View Beach!, holiday rental in Old Saybrook

Coastal Connecticut Apt: Walk to Sound View Beach!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Life's at ease, with an ocean breeze!, holiday rental in Old Saybrook

Life's at ease, with an ocean breeze!

3 bedrooms
2 bathrooms
Sleeps 6
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Stay just steps away from a beautiful private beach in Old Lyme!, holiday rental in Old Saybrook

Stay just steps away from a beautiful private beach in Old Lyme!

2 bedrooms
1 bathroom
Sleeps 8
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