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Old Saybrook Holiday Apartments

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68 rentals in Old Saybrook.
⚓Capt Nathaniel Clarke Historic HomesteadWeddings�Reunions❤Magnificent Yard�, holiday rental in Old Saybrook
⚓Capt Nathaniel Clarke Historic HomesteadWeddings�Reunions❤Magnificent Yard�, holiday rental in Old Saybrook
⚓Capt Nathaniel Clarke Historic HomesteadWeddings�Reunions❤Magnificent Yard�, holiday rental in Old Saybrook

⚓Capt Nathaniel Clarke Historic HomesteadWeddings�Reunions❤Magnificent Yard�

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Idyllic Saltaire Retreat at Cornfield Point, Old Saybrook, CT, holiday rental in Old Saybrook
Idyllic Saltaire Retreat at Cornfield Point, Old Saybrook, CT, holiday rental in Old Saybrook
Idyllic Saltaire Retreat at Cornfield Point, Old Saybrook, CT, holiday rental in Old Saybrook

Idyllic Saltaire Retreat at Cornfield Point, Old Saybrook, CT

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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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�� Steps to the Beach ⚓ Cozy Year Round Cottage � Pet Friendly, holiday rental in Old Saybrook
�� Steps to the Beach ⚓ Cozy Year Round Cottage � Pet Friendly, holiday rental in Old Saybrook
�� Steps to the Beach ⚓ Cozy Year Round Cottage � Pet Friendly, holiday rental in Old Saybrook

�� Steps to the Beach ⚓ Cozy Year Round Cottage � Pet Friendly

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Wonderful location, walk to beach, private yard, credit cards, holiday rental in Old Saybrook
Wonderful location, walk to beach, private yard, credit cards, holiday rental in Old Saybrook
Wonderful location, walk to beach, private yard, credit cards, holiday rental in Old Saybrook

Wonderful location, walk to beach, private yard, credit cards

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW, holiday rental in Old Saybrook
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW, holiday rental in Old Saybrook
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW, holiday rental in Old Saybrook

OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy cottage in Old Saybrook beach community, walking distance to private beach., holiday rental in Old Saybrook
Cozy cottage in Old Saybrook beach community, walking distance to private beach., holiday rental in Old Saybrook
Cozy cottage in Old Saybrook beach community, walking distance to private beach., holiday rental in Old Saybrook

Cozy cottage in Old Saybrook beach community, walking distance to private beach.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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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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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Cozy Yacht with Marina Views, holiday rental in Old Saybrook
Cozy Yacht with Marina Views, holiday rental in Old Saybrook
Cozy Yacht with Marina Views, holiday rental in Old Saybrook

Cozy Yacht with Marina Views

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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
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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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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
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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
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Quaint Cottage--Private Beach Access with Parking, holiday rental in Old Saybrook
Quaint Cottage--Private Beach Access with Parking, holiday rental in Old Saybrook
Quaint Cottage--Private Beach Access with Parking, holiday rental in Old Saybrook

Quaint Cottage--Private Beach Access with Parking

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Storybook Cottage, holiday rental in Old Saybrook
Storybook Cottage, holiday rental in Old Saybrook
Storybook Cottage, holiday rental in Old Saybrook

Storybook Cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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
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'Grandma's Cottage' w/ Sunroom: Walk to Beach, holiday rental in Old Saybrook
'Grandma's Cottage' w/ Sunroom: Walk to Beach, holiday rental in Old Saybrook
'Grandma's Cottage' w/ Sunroom: Walk to Beach, holiday rental in Old Saybrook

'Grandma's Cottage' w/ Sunroom: Walk to Beach

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cozy 3-bedroom house, front porch & super close to ocean., holiday rental in Old Saybrook
Cozy 3-bedroom house, front porch & super close to ocean., holiday rental in Old Saybrook
Cozy 3-bedroom house, front porch & super close to ocean., holiday rental in Old Saybrook

Cozy 3-bedroom house, front porch & super close to ocean.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Recently Updated, Old Saybrook Beach Cottage, holiday rental in Old Saybrook
Recently Updated, Old Saybrook Beach Cottage, holiday rental in Old Saybrook
Recently Updated, Old Saybrook Beach Cottage, holiday rental in Old Saybrook

Recently Updated, Old Saybrook Beach Cottage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning cottage, holiday rental in Old Saybrook
Stunning cottage, holiday rental in Old Saybrook
Stunning cottage, holiday rental in Old Saybrook

Stunning cottage

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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SeaStar Beach House -Knollwood Private beach -CLOSE WALK TO BEACH/OCEAN, holiday rental in Old Saybrook
SeaStar Beach House -Knollwood Private beach -CLOSE WALK TO BEACH/OCEAN, holiday rental in Old Saybrook
SeaStar Beach House -Knollwood Private beach -CLOSE WALK TO BEACH/OCEAN, holiday rental in Old Saybrook

SeaStar Beach House -Knollwood Private beach -CLOSE WALK TO BEACH/OCEAN

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Saybrook Manor House, Walk to Cove Beach!, holiday rental in Old Saybrook
NEW! Saybrook Manor House, Walk to Cove Beach!, holiday rental in Old Saybrook
NEW! Saybrook Manor House, Walk to Cove Beach!, holiday rental in Old Saybrook

NEW! Saybrook Manor House, Walk to Cove Beach!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Fully Updated Cornfield Point Beach House, Old Saybrook, CT, holiday rental in Old Saybrook
Fully Updated Cornfield Point Beach House, Old Saybrook, CT, holiday rental in Old Saybrook
Fully Updated Cornfield Point Beach House, Old Saybrook, CT, holiday rental in Old Saybrook

Fully Updated Cornfield Point Beach House, Old Saybrook, CT

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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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
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August & Sept weeks available- Beach Cottage in Old Saybrook CT, holiday rental in Old Saybrook
August & Sept weeks available- Beach Cottage in Old Saybrook CT, holiday rental in Old Saybrook
August & Sept weeks available- Beach Cottage in Old Saybrook CT, holiday rental in Old Saybrook

August & Sept weeks available- Beach Cottage in Old Saybrook CT

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Cozy Beach House - 5 min walk!  to  Knollwood Beach, holiday rental in Old Saybrook
Cozy Beach House - 5 min walk!  to  Knollwood Beach, holiday rental in Old Saybrook
Cozy Beach House - 5 min walk!  to  Knollwood Beach, holiday rental in Old Saybrook

Cozy Beach House - 5 min walk! to Knollwood Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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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
4 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Saltwater Gospel-Indian Town, Old Saybrook CT, holiday rental in Old Saybrook
Saltwater Gospel-Indian Town, Old Saybrook CT, holiday rental in Old Saybrook
Saltwater Gospel-Indian Town, Old Saybrook CT, holiday rental in Old Saybrook

Saltwater Gospel-Indian Town, Old Saybrook CT

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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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
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Perfect Academic Rental: 3-Bedroom Home w/large 4-season sun room, Walk to Beach, holiday rental in Old Saybrook
Perfect Academic Rental: 3-Bedroom Home w/large 4-season sun room, Walk to Beach, holiday rental in Old Saybrook
Perfect Academic Rental: 3-Bedroom Home w/large 4-season sun room, Walk to Beach, holiday rental in Old Saybrook

Perfect Academic Rental: 3-Bedroom Home w/large 4-season sun room, Walk to Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newly Renovated House - 5 Minute Walk to Private Beach!, holiday rental in Old Saybrook
Newly Renovated House - 5 Minute Walk to Private Beach!, holiday rental in Old Saybrook
Newly Renovated House - 5 Minute Walk to Private Beach!, holiday rental in Old Saybrook

Newly Renovated House - 5 Minute Walk to Private Beach!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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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
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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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1910 Beach home: CT's most exquisite private beach!, holiday rental in Old Saybrook
1910 Beach home: CT's most exquisite private beach!, holiday rental in Old Saybrook
1910 Beach home: CT's most exquisite private beach!, holiday rental in Old Saybrook

1910 Beach home: CT's most exquisite private beach!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
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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Luxury Cottage near Saybrook Point Marina- Dog Friendly!, holiday rental in Old Saybrook
Luxury Cottage near Saybrook Point Marina- Dog Friendly!, holiday rental in Old Saybrook
Luxury Cottage near Saybrook Point Marina- Dog Friendly!, holiday rental in Old Saybrook

Luxury Cottage near Saybrook Point Marina- Dog Friendly!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cape Overlooking South Cove of Old Saybrook, holiday rental in Old Saybrook
Cape Overlooking South Cove of Old Saybrook, holiday rental in Old Saybrook
Cape Overlooking South Cove of Old Saybrook, holiday rental in Old Saybrook

Cape Overlooking South Cove of Old Saybrook

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pickleball, Tennis, Basketball, Kids Playground, Kayak, Jog, Walk. & Bike, holiday rental in Old Saybrook
Pickleball, Tennis, Basketball, Kids Playground, Kayak, Jog, Walk. & Bike, holiday rental in Old Saybrook
Pickleball, Tennis, Basketball, Kids Playground, Kayak, Jog, Walk. & Bike, holiday rental in Old Saybrook

Pickleball, Tennis, Basketball, Kids Playground, Kayak, Jog, Walk. & Bike

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private Oceanfront sleeps 12 ~ 3bds 2bth Linens included, holiday rental in Old Saybrook
Private Oceanfront sleeps 12 ~ 3bds 2bth Linens included, holiday rental in Old Saybrook
Private Oceanfront sleeps 12 ~ 3bds 2bth Linens included, holiday rental in Old Saybrook

Private Oceanfront sleeps 12 ~ 3bds 2bth Linens included

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Charming Old Saybrook Home: Half-Mi to Sand & Sea!, holiday rental in Old Saybrook
Charming Old Saybrook Home: Half-Mi to Sand & Sea!, holiday rental in Old Saybrook
Charming Old Saybrook Home: Half-Mi to Sand & Sea!, holiday rental in Old Saybrook

Charming Old Saybrook Home: Half-Mi to Sand & Sea!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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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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
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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
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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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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
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Spectacular Home with Deep Water Dock, holiday rental in Old Saybrook
Spectacular Home with Deep Water Dock, holiday rental in Old Saybrook
Spectacular Home with Deep Water Dock, holiday rental in Old Saybrook

Spectacular Home with Deep Water Dock

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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
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Showing results 1-50 of 68
Frequently Asked Questions about Old Saybrook