Vacation rentals in Old Saybrook, CT

92 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Old Saybrook, CT

Beautuful, private studio apartment with access to hiking trails, kayaks, bikes. - Old Saybrook, CT

Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.

Apartment, Old Saybrook

Beautuful, private studio apartment with access to hiking trails, kayaks, bikes. is a apartment in Old Saybrook. This stay gives travelers a comfortable base for exploring the area,…

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About Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.

Beautuful, private studio apartment with access to hiking trails, kayaks, bikes. is a apartment in Old Saybrook. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $951.

From$136/night
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Saybrook Point Cottage - Charming and Private - Old Saybrook, CT

Saybrook Point Cottage - Charming and Private

Cottage, Old Saybrook

Saybrook Point Cottage - Charming and Private is a cottage in Old Saybrook, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Saybrook Point Cottage - Charming and Private

Saybrook Point Cottage - Charming and Private is a cottage in Old Saybrook, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,543.

From$220/night
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The Nest at Black Hall - Old Saybrook, CT

The Nest at Black Hall

Apartment, Old Saybrook

The Nest at Black Hall is a apartment in Old Saybrook, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About The Nest at Black Hall

The Nest at Black Hall is a apartment in Old Saybrook, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,547.

From$221/night
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Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach - Old Saybrook, CT

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

Cottage, Old Saybrook

Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach is a cottage in Old Saybrook, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable…

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

Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach is a cottage in Old Saybrook, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,799.

From$257/night
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Browse Vacation Rentals with a Pool in Old Saybrook, CT

Add a pool to the search when you want an easy place to cool off between outings.

Orient Point Waterfront Home – Private Beach & Stunning Views - Old Saybrook, CT

Orient Point Waterfront Home – Private Beach & Stunning Views

Holiday Home, Old Saybrook

Orient Point Waterfront Home – Private Beach & Stunning Views is a holiday home in Old Saybrook, with pool access and easy beach access. This stay gives travelers a comfortable base for…

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About Orient Point Waterfront Home – Private Beach & Stunning Views

Orient Point Waterfront Home – Private Beach & Stunning Views is a holiday home in Old Saybrook, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,014.

From$1,002/night
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Luxury Riverfront Estate - Pool, Spa, Tennis, & Pond - Old Saybrook, CT

Luxury Riverfront Estate - Pool, Spa, Tennis, & Pond

Villa, Old Saybrook

Luxury Riverfront Estate - Pool, Spa, Tennis, & Pond is a villa in Old Saybrook, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Luxury Riverfront Estate - Pool, Spa, Tennis, & Pond

Luxury Riverfront Estate - Pool, Spa, Tennis, & Pond is a villa in Old Saybrook, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,647.

From$1,378/night
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Private 2-acre coastal compound with pool + optional guest cottage in Westbrook - Old Saybrook, CT

Private 2-acre coastal compound with pool + optional guest cottage in Westbrook

Holiday Home, Old Saybrook

Private 2-acre coastal compound with pool + optional guest cottage in Westbrook is a holiday home in Old Saybrook, with pool access and kitchen access. This stay gives travelers a…

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About Private 2-acre coastal compound with pool + optional guest cottage in Westbrook

Private 2-acre coastal compound with pool + optional guest cottage in Westbrook is a holiday home in Old Saybrook, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,965.

From$1,424/night
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Private Vineyard Estate in Orient Village w Pool / AC / Walk to Beach & Town - Old Saybrook, CT

Private Vineyard Estate in Orient Village w Pool / AC / Walk to Beach & Town

Holiday Home, Old Saybrook

Private Vineyard Estate in Orient Village w Pool / AC / Walk to Beach & Town is a holiday home in Old Saybrook, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Private Vineyard Estate in Orient Village w Pool / AC / Walk to Beach & Town

Private Vineyard Estate in Orient Village w Pool / AC / Walk to Beach & Town is a holiday home in Old Saybrook, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $14,711.

From$2,102/night
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Best Old Saybrook, CT vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Shoreline Oasis - Old Saybrook, CT

Shoreline Oasis

Apartment, Old Saybrook

Shoreline Oasis is a apartment in Old Saybrook, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Shoreline Oasis

Shoreline Oasis is a apartment in Old Saybrook, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,357.

From$194/night
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Giants Neck Heights. Booking Fall 2025! - Old Saybrook, CT

Giants Neck Heights. Booking Fall 2025!

Holiday Home, Old Saybrook

Giants Neck Heights. Booking Fall 2025! is a holiday home in Old Saybrook, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Giants Neck Heights. Booking Fall 2025!

Giants Neck Heights. Booking Fall 2025! is a holiday home in Old Saybrook, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,673.

From$239/night
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The Mast at Soundview · Beach+Ocean+Sunrise - Old Saybrook, CT

The Mast at Soundview · Beach+Ocean+Sunrise

Apartment, Old Saybrook

The Mast at Soundview · Beach+Ocean+Sunrise is a apartment in Old Saybrook, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About The Mast at Soundview · Beach+Ocean+Sunrise

The Mast at Soundview · Beach+Ocean+Sunrise is a apartment in Old Saybrook, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,193.

From$313/night
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The Stern at Soundview · Beach+Ocean+Sunrise - Old Saybrook, CT

The Stern at Soundview · Beach+Ocean+Sunrise

Apartment, Old Saybrook

The Stern at Soundview · Beach+Ocean+Sunrise is a apartment in Old Saybrook, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise is a apartment in Old Saybrook, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,193.

From$313/night
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Best Pet-Friendly Vacation Rentals in Old Saybrook, CT

Bring your pet along with stays that welcome four-legged travelers.

Life on the Farm - Old Saybrook, CT

Life on the Farm

Apartment, Old Saybrook

Life on the Farm is a apartment in Old Saybrook, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Life on the Farm

Life on the Farm is a apartment in Old Saybrook, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,192.

From$170/night
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Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more - Old Saybrook, CT

Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more

Cottage, Old Saybrook

Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more is a cottage in Old Saybrook, with pet-friendly space and room for a group. This stay gives travelers a…

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About Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more

Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more is a cottage in Old Saybrook, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,737.

From$391/night
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Now available for short term rentals during the off season. - Old Saybrook, CT

Now available for short term rentals during the off season.

Holiday Home, Old Saybrook

Now available for short term rentals during the off season. is a holiday home in Old Saybrook, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Now available for short term rentals during the off season.

Now available for short term rentals during the off season. is a holiday home in Old Saybrook, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,932.

From$419/night
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Peace Barn in the heart of the CT River Valley - Old Saybrook, CT

Peace Barn in the heart of the CT River Valley

Holiday Home, Old Saybrook

Peace Barn in the heart of the CT River Valley is a holiday home in Old Saybrook, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Peace Barn in the heart of the CT River Valley

Peace Barn in the heart of the CT River Valley is a holiday home in Old Saybrook, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, internet, and non smoking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,967.

From$424/night
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Best Old Saybrook, CT vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Keel at Soundview · Beach+OceanView+Sunrise - Old Saybrook, CT

Keel at Soundview · Beach+OceanView+Sunrise

Apartment, Old Saybrook

Keel at Soundview · Beach+OceanView+Sunrise is a apartment in Old Saybrook, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Keel at Soundview · Beach+OceanView+Sunrise

Keel at Soundview · Beach+OceanView+Sunrise is a apartment in Old Saybrook, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,416.

From$345/night
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Forecastle at Soundview · Beach+OceanView+Sunrise - Old Saybrook, CT

Forecastle at Soundview · Beach+OceanView+Sunrise

Apartment, Old Saybrook

Forecastle at Soundview · Beach+OceanView+Sunrise is a apartment in Old Saybrook, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Forecastle at Soundview · Beach+OceanView+Sunrise

Forecastle at Soundview · Beach+OceanView+Sunrise is a apartment in Old Saybrook, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,550.

From$364/night
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Hatch at Soundview · Beach+OceanView+Sunrise - Old Saybrook, CT

Hatch at Soundview · Beach+OceanView+Sunrise

Apartment, Old Saybrook

Hatch at Soundview · Beach+OceanView+Sunrise is a apartment in Old Saybrook, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Hatch at Soundview · Beach+OceanView+Sunrise

Hatch at Soundview · Beach+OceanView+Sunrise is a apartment in Old Saybrook, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,550.

From$364/night
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Beautiful Spacious Studio in a Beach Community - Old Saybrook, CT

Beautiful Spacious Studio in a Beach Community

Apartment, Old Saybrook

Beautiful Spacious Studio in a Beach Community is a apartment in Old Saybrook, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Beautiful Spacious Studio in a Beach Community

Beautiful Spacious Studio in a Beach Community is a apartment in Old Saybrook, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,577.

From$368/night
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Our Favorite Family-Friendly Vacation Rentals in Old Saybrook, CT

Plan a trip with stays that give families more room to spread out.

2Bdr Beachfront; 11B second floor, Old Colony Beach , CT - Old Saybrook, CT

2Bdr Beachfront; 11B second floor, Old Colony Beach , CT

Cottage, Old Saybrook

2Bdr Beachfront; 11B second floor, Old Colony Beach , CT is a cottage in Old Saybrook, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring…

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About 2Bdr Beachfront; 11B second floor, Old Colony Beach , CT

2Bdr Beachfront; 11B second floor, Old Colony Beach , CT is a cottage in Old Saybrook, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,314.

From$331/night
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Cozy/comfy/peaceful beach home - Old Saybrook, CT

Cozy/comfy/peaceful beach home

Cottage, Old Saybrook

Cozy/comfy/peaceful beach home is a cottage in Old Saybrook, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy/comfy/peaceful beach home

Cozy/comfy/peaceful beach home is a cottage in Old Saybrook, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,496.

From$357/night
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A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve - Old Saybrook, CT

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

Cottage, Old Saybrook

A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve is a cottage in Old Saybrook, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About 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 is a cottage in Old Saybrook, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,143.

From$449/night
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Old Saybrook family gem very close to local beaches! - Old Saybrook, CT

Old Saybrook family gem very close to local beaches!

Holiday Home, Old Saybrook

Old Saybrook family gem very close to local beaches! is a holiday home in Old Saybrook, with easy beach access, parking, and room for a group. This stay gives travelers a comfortable base…

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About Old Saybrook family gem very close to local beaches!

Old Saybrook family gem very close to local beaches! is a holiday home in Old Saybrook, with easy beach access, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, parking, free parking, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,347.

From$478/night
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