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Holiday Rentals in Old Saybrook

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56 rentals in Old Saybrook.
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Beachfront Classic New England Home With Direct Views Of Long Island Sound, holiday rental in Old Saybrook
Beachfront Classic New England Home With Direct Views Of Long Island Sound, holiday rental in Old Saybrook
Beachfront Classic New England Home With Direct Views Of Long Island Sound, holiday rental in Old Saybrook

Beachfront Classic New England Home With Direct Views Of Long Island Sound

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Saybrook Point Cottage  - Charming and Private, holiday rental in Old Saybrook
Saybrook Point Cottage  - Charming and Private, holiday rental in Old Saybrook
Saybrook Point Cottage  - Charming and Private, holiday rental in Old Saybrook

Saybrook Point Cottage - Charming and Private

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Spacious And Luxurious Beach Home Steps From The Water - Sanitized for guests., holiday rental in Old Saybrook
Spacious And Luxurious Beach Home Steps From The Water - Sanitized for guests., holiday rental in Old Saybrook
Spacious And Luxurious Beach Home Steps From The Water - Sanitized for guests., holiday rental in Old Saybrook

Spacious And Luxurious Beach Home Steps From The Water - Sanitized for guests.

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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Family Friendly, Newly Renovated Cottage - Chalker Beach, holiday rental in Old Saybrook
Family Friendly, Newly Renovated Cottage - Chalker Beach, holiday rental in Old Saybrook
Family Friendly, Newly Renovated Cottage - Chalker Beach, holiday rental in Old Saybrook

Family Friendly, Newly Renovated Cottage - Chalker Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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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, holiday rental in Old Saybrook
Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach, holiday rental in Old Saybrook

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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3 Minute Walk To Beach in Sought After Indian Town Private Beach Assoc., holiday rental in Old Saybrook
3 Minute Walk To Beach in Sought After Indian Town Private Beach Assoc., holiday rental in Old Saybrook
3 Minute Walk To Beach in Sought After Indian Town Private Beach Assoc., holiday rental in Old Saybrook

3 Minute Walk To Beach in Sought After Indian Town Private Beach Assoc.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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adorable ranch in beach community, holiday rental in Old Saybrook
adorable ranch in beach community, holiday rental in Old Saybrook
adorable ranch in beach community, holiday rental in Old Saybrook

adorable ranch in beach community

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook, holiday rental in Old Saybrook
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook, holiday rental in Old Saybrook
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook, holiday rental in Old Saybrook

Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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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., holiday rental in Old Saybrook
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.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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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., holiday rental in Old Saybrook
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.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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!, holiday rental in Old Saybrook
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!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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3 BR, 3.5 BA luxury Home sleeps 7 GreatViews, Wildlife. Academic Rental Possible, holiday rental in Old Saybrook
3 BR, 3.5 BA luxury Home sleeps 7 GreatViews, Wildlife. Academic Rental Possible, holiday rental in Old Saybrook
3 BR, 3.5 BA luxury Home sleeps 7 GreatViews, Wildlife. Academic Rental Possible, holiday rental in Old Saybrook

3 BR, 3.5 BA luxury Home sleeps 7 GreatViews, Wildlife. Academic Rental Possible

Holiday Rental House
3 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
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Vacation at Knollwood Beach in beautiful Old Saybrook!, holiday rental in Old Saybrook
Vacation at Knollwood Beach in beautiful Old Saybrook!, holiday rental in Old Saybrook
Vacation at Knollwood Beach in beautiful Old Saybrook!, holiday rental in Old Saybrook

Vacation at Knollwood Beach in beautiful Old Saybrook!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Convenient and Cute in Downtown Old Saybrook, holiday rental in Old Saybrook
Convenient and Cute in Downtown Old Saybrook, holiday rental in Old Saybrook
Convenient and Cute in Downtown Old Saybrook, holiday rental in Old Saybrook

Convenient and Cute in Downtown Old Saybrook

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Luxurious Beach Home!, holiday rental in Old Saybrook
Luxurious Beach Home!, holiday rental in Old Saybrook
Luxurious Beach Home!, holiday rental in Old Saybrook

Luxurious Beach Home!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Welcome to Cornfield Coop, holiday rental in Old Saybrook
Welcome to Cornfield Coop, holiday rental in Old Saybrook
Welcome to Cornfield Coop, holiday rental in Old Saybrook

Welcome to Cornfield Coop

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Brand New Luxurious Cottage - Steps to the Beach, Pet Friendly!, holiday rental in Old Saybrook
Brand New Luxurious Cottage - Steps to the Beach, Pet Friendly!, holiday rental in Old Saybrook
Brand New Luxurious Cottage - Steps to the Beach, Pet Friendly!, holiday rental in Old Saybrook

Brand New Luxurious Cottage - Steps to the Beach, Pet Friendly!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Waterfront Relaxation!, holiday rental in Old Saybrook
Waterfront Relaxation!, holiday rental in Old Saybrook
Waterfront Relaxation!, holiday rental in Old Saybrook

Waterfront Relaxation!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Available September 10th on, holiday rental in Old Saybrook
Available September 10th on, holiday rental in Old Saybrook
Available September 10th on, holiday rental in Old Saybrook

Available September 10th on

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Luxury Cottage steps away from Saybrook Point Marina, holiday rental in Old Saybrook
Luxury Cottage steps away from Saybrook Point Marina, holiday rental in Old Saybrook
Luxury Cottage steps away from Saybrook Point Marina, holiday rental in Old Saybrook

Luxury Cottage steps away from Saybrook Point Marina

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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A GETAWAY TO REMEMBER AT THE JEWEL BOX * NORTH COVE, holiday rental in Old Saybrook
A GETAWAY TO REMEMBER AT THE JEWEL BOX * NORTH COVE, holiday rental in Old Saybrook
A GETAWAY TO REMEMBER AT THE JEWEL BOX * NORTH COVE, holiday rental in Old Saybrook

A GETAWAY TO REMEMBER AT THE JEWEL BOX * NORTH COVE

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Old Saybrook Memories Await at the Cashmere Cottage!, holiday rental in Old Saybrook
Old Saybrook Memories Await at the Cashmere Cottage!, holiday rental in Old Saybrook
Old Saybrook Memories Await at the Cashmere Cottage!, holiday rental in Old Saybrook

Old Saybrook Memories Await at the Cashmere Cottage!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Downtown, Main Street, Center of it All Location, holiday rental in Old Saybrook
Downtown, Main Street, Center of it All Location, holiday rental in Old Saybrook
Downtown, Main Street, Center of it All Location, holiday rental in Old Saybrook

Downtown, Main Street, Center of it All Location

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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5 Bedroom Cottage Steps From The Beach * Great Hammock Beach, holiday rental in Old Saybrook
5 Bedroom Cottage Steps From The Beach * Great Hammock Beach, holiday rental in Old Saybrook
5 Bedroom Cottage Steps From The Beach * Great Hammock Beach, holiday rental in Old Saybrook

5 Bedroom Cottage Steps From The Beach * Great Hammock Beach

Holiday Rental House
5 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
More info
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Saybrook Manor House, Walk to Cove Beach!, holiday rental in Old Saybrook
Saybrook Manor House, Walk to Cove Beach!, holiday rental in Old Saybrook
Saybrook Manor House, Walk to Cove Beach!, holiday rental in Old Saybrook

Saybrook Manor House, Walk to Cove Beach!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Waterfront Beachfront, holiday rental in Old Saybrook
Waterfront Beachfront, holiday rental in Old Saybrook
Waterfront Beachfront, holiday rental in Old Saybrook

Waterfront Beachfront

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Cornfield Point Beachfront Small Cottage, holiday rental in Old Saybrook
Cornfield Point Beachfront Small Cottage, holiday rental in Old Saybrook
Cornfield Point Beachfront Small Cottage, holiday rental in Old Saybrook

Cornfield Point Beachfront Small Cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Stunning Seascape Home For A Dream Family Holiday, holiday rental in Old Saybrook
Stunning Seascape Home For A Dream Family Holiday, holiday rental in Old Saybrook
Stunning Seascape Home For A Dream Family Holiday, holiday rental in Old Saybrook

Stunning Seascape Home For A Dream Family Holiday

Holiday Rental House
9 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
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Saybrook Almost Beach-Front, Private Beach,  Boat Launch, Shallow Dock, Secluded, holiday rental in Old Saybrook
Saybrook Almost Beach-Front, Private Beach,  Boat Launch, Shallow Dock, Secluded, holiday rental in Old Saybrook
Saybrook Almost Beach-Front, Private Beach,  Boat Launch, Shallow Dock, Secluded, holiday rental in Old Saybrook

Saybrook Almost Beach-Front, Private Beach, Boat Launch, Shallow Dock, Secluded

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Exhale at Old Saybrook's Chic Retreat!, holiday rental in Old Saybrook
Exhale at Old Saybrook's Chic Retreat!, holiday rental in Old Saybrook
Exhale at Old Saybrook's Chic Retreat!, holiday rental in Old Saybrook

Exhale at Old Saybrook's Chic Retreat!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Direct Waterfront Home - Enjoy all Summer Long, holiday rental in Old Saybrook
Direct Waterfront Home - Enjoy all Summer Long, holiday rental in Old Saybrook
Direct Waterfront Home - Enjoy all Summer Long, holiday rental in Old Saybrook

Direct Waterfront Home - Enjoy all Summer Long

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Modern Beach & Ocean Front House, holiday rental in Old Saybrook
Modern Beach & Ocean Front House, holiday rental in Old Saybrook
Modern Beach & Ocean Front House, holiday rental in Old Saybrook

Modern Beach & Ocean Front House

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Lovely 3 BR Beach house with beach just a 1 block walk away, holiday rental in Old Saybrook
Lovely 3 BR Beach house with beach just a 1 block walk away, holiday rental in Old Saybrook
Lovely 3 BR Beach house with beach just a 1 block walk away, holiday rental in Old Saybrook

Lovely 3 BR Beach house with beach just a 1 block walk away

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Cornfield Point Beachfront Cottage, holiday rental in Old Saybrook
Cornfield Point Beachfront Cottage, holiday rental in Old Saybrook
Cornfield Point Beachfront Cottage, holiday rental in Old Saybrook

Cornfield Point Beachfront Cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beach House steps to private beaches in sought after location!, holiday rental in Old Saybrook
Beach House steps to private beaches in sought after location!, holiday rental in Old Saybrook
Beach House steps to private beaches in sought after location!, holiday rental in Old Saybrook

Beach House steps to private beaches in sought after location!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Chalker Beach House Steps to the Water!, holiday rental in Old Saybrook
Chalker Beach House Steps to the Water!, holiday rental in Old Saybrook
Chalker Beach House Steps to the Water!, holiday rental in Old Saybrook

Chalker Beach House Steps to the Water!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Lovely Cornfield Point home away from home, holiday rental in Old Saybrook
Lovely Cornfield Point home away from home, holiday rental in Old Saybrook
Lovely Cornfield Point home away from home, holiday rental in Old Saybrook

Lovely Cornfield Point home away from home

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beach front home, holiday rental in Old Saybrook
Beach front home, holiday rental in Old Saybrook
Beach front home, holiday rental in Old Saybrook

Beach front home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Pristine cottage at Cornfield Point, holiday rental in Old Saybrook
Pristine cottage at Cornfield Point, holiday rental in Old Saybrook
Pristine cottage at Cornfield Point, holiday rental in Old Saybrook

Pristine cottage at Cornfield Point

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful waterfront home with private sand beach and amazing views, holiday rental in Old Saybrook
Beautiful waterfront home with private sand beach and amazing views, holiday rental in Old Saybrook
Beautiful waterfront home with private sand beach and amazing views, holiday rental in Old Saybrook

Beautiful waterfront home with private sand beach and amazing views

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Updated beach house with stunning views and one block to private Chalker Beach., holiday rental in Old Saybrook
Updated beach house with stunning views and one block to private Chalker Beach., holiday rental in Old Saybrook
Updated beach house with stunning views and one block to private Chalker Beach., holiday rental in Old Saybrook

Updated beach house with stunning views and one block to private Chalker Beach.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Marsh View Home!, holiday rental in Old Saybrook
Marsh View Home!, holiday rental in Old Saybrook
Marsh View Home!, holiday rental in Old Saybrook

Marsh View Home!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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★South Cove Seaside Cottage★5 min to Harveys Beach, holiday rental in Old Saybrook
★South Cove Seaside Cottage★5 min to Harveys Beach, holiday rental in Old Saybrook
★South Cove Seaside Cottage★5 min to Harveys Beach, holiday rental in Old Saybrook

★South Cove Seaside Cottage★5 min to Harveys Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Fantastic pool home in park-like setting on Connecticut Shore, holiday rental in Old Saybrook
Fantastic pool home in park-like setting on Connecticut Shore, holiday rental in Old Saybrook
Fantastic pool home in park-like setting on Connecticut Shore, holiday rental in Old Saybrook

Fantastic pool home in park-like setting on Connecticut Shore

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Gorgeous top floor, high ceiling & brand new apartment!, holiday rental in Old Saybrook
Gorgeous top floor, high ceiling & brand new apartment!, holiday rental in Old Saybrook
Gorgeous top floor, high ceiling & brand new apartment!, holiday rental in Old Saybrook

Gorgeous top floor, high ceiling & brand new apartment!

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Newly Renovated Private Quiet Cape 1/2 mile from the beach, holiday rental in Old Saybrook
Newly Renovated Private Quiet Cape 1/2 mile from the beach, holiday rental in Old Saybrook
Newly Renovated Private Quiet Cape 1/2 mile from the beach, holiday rental in Old Saybrook

Newly Renovated Private Quiet Cape 1/2 mile from the beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Paradise in Old Saybrook, holiday rental in Old Saybrook
Paradise in Old Saybrook, holiday rental in Old Saybrook
Paradise in Old Saybrook, holiday rental in Old Saybrook

Paradise in Old Saybrook

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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⚓️Perfect Summer Oasis with nautical touches….. 59 steps to private beach ⛱, holiday rental in Old Saybrook
⚓️Perfect Summer Oasis with nautical touches….. 59 steps to private beach ⛱, holiday rental in Old Saybrook
⚓️Perfect Summer Oasis with nautical touches….. 59 steps to private beach ⛱, holiday rental in Old Saybrook

⚓️Perfect Summer Oasis with nautical touches….. 59 steps to private beach ⛱

Holiday Rental House
5 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Renovated 3BR in Old Saybrook, holiday rental in Old Saybrook
Renovated 3BR in Old Saybrook, holiday rental in Old Saybrook
Renovated 3BR in Old Saybrook, holiday rental in Old Saybrook

Renovated 3BR in Old Saybrook

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beach community with private beaches, holiday rental in Old Saybrook
Beach community with private beaches, holiday rental in Old Saybrook
Beach community with private beaches, holiday rental in Old Saybrook

Beach community with private beaches

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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