Old Saybrook, Connecticut

Vacation Rentals in Old Saybrook, Connecticut

Discover 82 vacation rental properties in Old Saybrook. From 1 to 9 bedrooms. Average $480/night. 100% have pools.

82 verified listings Book securely on VRBO Prices updated March 2026

82 properties available

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

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

3 beds 1 bath
PoolA/CWiFiBalcony
$203/night
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Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook

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

4 beds
PoolA/CWiFiBalcony
$226/night
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Charming Old Saybrook Home: Half-Mi to Sand & Sea!

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

3 beds 2 baths
PoolA/CWiFiBalcony
$217/night
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Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

3 beds 2 baths
PoolA/CWiFiBalcony
$843/night
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Walk to Private Beach - Saybrook Manor Vacation Rentals

Walk to Private Beach - Saybrook Manor Vacation Rentals

3 beds 1 bath
PoolA/CWiFiBalcony
$239/night
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Saybrook Point Cottage - Charming and Private

Saybrook Point Cottage - Charming and Private

1 bed 1 bath
PoolA/CWiFiBalcony
$161/night
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Cozy 3-bedroom house, front porch & super close to ocean.

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

3 beds 2 baths
PoolA/CWiFiBalcony
$151/night
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Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly

Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly

1 bed 1 bath
PoolA/CWiFiBalcony
$201/night
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Idyllic Beach Retreat at Cornfield Point, Old Saybrook, CT

Idyllic Beach Retreat at Cornfield Point, Old Saybrook, CT

3 beds 2 baths
PoolA/CWiFiBalcony
$357/night
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August & Sept weeks available- Beach Cottage in Old Saybrook CT

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

2 beds 1 bath
PoolA/CWiFiBalcony
$298/night
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adorable ranch in beach community

adorable ranch in beach community

3 beds 1 bath
PoolA/CWiFiBalcony
$422/night
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Fenwood Coastal Getaway Private Beach Access

Fenwood Coastal Getaway Private Beach Access

3 beds 2 baths
PoolA/CWiFiBalcony
$343/night
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Family Friendly, Beach Themed Cottage - Chalker Beach

Family Friendly, Beach Themed Cottage - Chalker Beach

3 beds 1 bath
PoolA/CWiFiBalcony
$235/night
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Downtown Old Saybrook Oasis

Downtown Old Saybrook Oasis

4 beds 2 baths
PoolA/CWiFiBalcony
$389/night
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Beach Front Cottage-Private Beach

Beach Front Cottage-Private Beach

3 beds 2 baths
PoolA/CWiFiBalcony
$1,001/night
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Cozy cottage in Old Saybrook beach community, walking distance to private beach.

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

2 beds 1 bath
PoolA/CWiFiBalcony
$300/night
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OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW

OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW

4 beds 2 baths
PoolA/CWiFiBalcony
$777/night
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Great Hammcock Getaway

Great Hammcock Getaway

3 beds 1 bath
PoolA/CWiFiBalcony
$286/night
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54 Steps to the Beach

54 Steps to the Beach

4 beds 2 baths
PoolA/CWiFiBalcony
$363/night
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Cozy Yacht with Marina Views

Cozy Yacht with Marina Views

2 beds 1 bath
PoolA/CWiFiBalcony
$202/night
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Convenient and cute in Downtown Old Saybrook

Convenient and cute in Downtown Old Saybrook

1 bed 1 bath
PoolA/CWiFiBalcony
$126/night
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Beach House steps to private beaches in sought after location!

Beach House steps to private beaches in sought after location!

2 beds 1 bath
PoolA/CWiFiBalcony
$258/night
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Luxury & Premier Location-THE CASHMERE COTTAGE! Near the Kate / Saybrook Point!

Luxury & Premier Location-THE CASHMERE COTTAGE! Near the Kate / Saybrook Point!

2 beds 2 baths
PoolA/CWiFiBalcony
$318/night
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Luxury Cottage walking distance to Saybrook Point Marina

Luxury Cottage walking distance to Saybrook Point Marina

3 beds 2 baths
PoolA/CWiFiBalcony
$362/night
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⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

5 beds 2 baths
PoolA/CWiFiBalcony
$555/night
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Charming Old Saybrook Cottage < 1 Mi to Beach

Charming Old Saybrook Cottage < 1 Mi to Beach

4 beds 2 baths
PoolA/CWiFiBalcony
$373/night
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SHORE BEATS WORK - Cornfield Point Beach - Family Friendly!

SHORE BEATS WORK - Cornfield Point Beach - Family Friendly!

3 beds 2 baths
PoolA/CWiFiBalcony
$470/night
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3 BR, 3.5 BA luxury Home sleeps 7 GreatViews, Wildlife. Academic Rental Possible

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

3 beds 2 baths
PoolA/CWiFiBalcony
$636/night
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Fully Updated Cornfield Point Beach House, Old Saybrook, CT

Fully Updated Cornfield Point Beach House, Old Saybrook, CT

3 beds 1 bath
PoolA/CWiFiBalcony
$349/night
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Great family home, fenced in back yard and Weber grill.

Great family home, fenced in back yard and Weber grill.

3 beds 1 bath
PoolA/CWiFiBalcony
$343/night
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Saybrook Almost Beach-Front, Private Beach, Boat Launch, Shallow Dock, Secluded

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

4 beds 1 bath
PoolA/CWiFiBalcony
$325/night
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Cozy Beach House - 5 min walk! to Knollwood Beach

Cozy Beach House - 5 min walk! to Knollwood Beach

3 beds 2 baths
PoolA/CWiFiBalcony
$325/night
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Cornfield Point Cottage

Cornfield Point Cottage

4 beds 2 baths
PoolA/CWiFiBalcony
$900/night
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Beach house with views that has access to Tennis, Basketball and Private Beach.

Beach house with views that has access to Tennis, Basketball and Private Beach.

3 beds 2 baths
PoolA/CWiFiBalcony
$465/night
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All Year Beach Home

All Year Beach Home

3 beds 2 baths
PoolA/CWiFiBalcony
$135/night
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Delightful retreat in the heart of Old Saybrook. Summertime bliss!

Delightful retreat in the heart of Old Saybrook. Summertime bliss!

2 beds 1 bath
PoolA/CWiFiBalcony
$169/night
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Wonderful location, walk to beach, private yard, credit cards

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

2 beds 1 bath
PoolA/CWiFiBalcony
$267/night
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Exquisite Beach Villa In Ground pool and Spacious Bermuda room! 2 living Rooms!

Exquisite Beach Villa In Ground pool and Spacious Bermuda room! 2 living Rooms!

3 beds 2 baths
PoolA/CWiFiBalcony
$558/night
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Convenience and Privacy in Exclusive North Cove! Close to beaches and downtown!

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

3 beds 1 bath
PoolA/CWiFiBalcony
$338/night
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5 Bedroom Cottage Steps From The Beach @ Great Hammock Beach - JULY RENTAL ONLY

5 Bedroom Cottage Steps From The Beach @ Great Hammock Beach - JULY RENTAL ONLY

5 beds 1 bath
PoolA/CWiFiBalcony
$351/night
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Waterfront Beachfront

Waterfront Beachfront

4 beds 1 bath
PoolA/CWiFiBalcony
$572/night
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Pristine cottage at Cornfield Point

Pristine cottage at Cornfield Point

3 beds 2 baths
PoolA/CWiFiBalcony
$451/night
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Spectacular Home with Deep Water Dock

Spectacular Home with Deep Water Dock

3 beds 1 bath
PoolA/CWiFiBalcony
$400/night
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Storybook Cottage

Storybook Cottage

3 beds 1 bath
PoolA/CWiFiBalcony
$244/night
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A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve

A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve

2 beds 1 bath
PoolA/CWiFiBalcony
$345/night
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Stunning cottage

Stunning cottage

3 beds 1 bath
PoolA/CWiFiBalcony
$330/night
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Saltwater Gospel-Indian Town, Old Saybrook CT

Saltwater Gospel-Indian Town, Old Saybrook CT

2 beds 1 bath
PoolA/CWiFiBalcony
$335/night
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Cape Overlooking South Cove of Old Saybrook

Cape Overlooking South Cove of Old Saybrook

3 beds 1 bath
PoolA/CWiFiBalcony
$386/night
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Showing 48 of 82 properties

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