Vacation rentals in Shelter Island, NY

Best vacation rentals and Airbnb offers in Shelter Island, NY

The Shoals Suites & Slips

Apartment, Shelter Island

The Shoals Suites & Slips is a apartment in Shelter Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About The Shoals Suites & Slips

The Shoals Suites & Slips is a apartment in Shelter Island, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,986.

From$373/night

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West Neck Guesthouse

B & B, Shelter Island

West Neck Guesthouse is a b & b in Shelter Island, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About West Neck Guesthouse

West Neck Guesthouse is a b & b in Shelter Island, with pool access and parking. 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,180.

From$398/night

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North Beach Fork Beach House

Holiday Home, Shelter Island

North Beach Fork Beach House is a holiday home in Shelter Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About North Beach Fork Beach House

North Beach Fork Beach House is a holiday home in Shelter Island, 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 $2,856.

From$408/night

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Charming, Renovated Island Cottage - Shelter Island License #: 012-2017

Cottage, Shelter Island

Charming, Renovated Island Cottage - Shelter Island License #: 012-2017 is a cottage in Shelter Island, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Charming, Renovated Island Cottage - Shelter Island License #: 012-2017

Charming, Renovated Island Cottage - Shelter Island License #: 012-2017 is a cottage in Shelter Island, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,061.

From$437/night

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Waterfront vacation rentals in Shelter Island, NY

Discover vacation rentals close to the coast, water, and beach areas around Shelter Island, NY.

Waterfront Hot Tub Retreat w Kayaks | Kayak Point

Holiday Home, Shelter Island

Waterfront Hot Tub Retreat w Kayaks · Kayak Point is a holiday home in Shelter Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Waterfront Hot Tub Retreat w Kayaks | Kayak Point

Waterfront Hot Tub Retreat w Kayaks · Kayak Point is a holiday home in Shelter Island, 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: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,877.

From$697/night

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Shelter Island, Waterfront, Lazy Days With Stunning Views

Holiday Home, Shelter Island

Shelter Island, Waterfront, Lazy Days With Stunning Views is a holiday home in Shelter Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable…

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About Shelter Island, Waterfront, Lazy Days With Stunning Views

Shelter Island, Waterfront, Lazy Days With Stunning Views is a holiday home in Shelter Island, 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 $7,515.

From$1,074/night

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Relax at a private beach! Three bedrooms await you near Shelter Island beaches!

Holiday Home, Shelter Island

Relax at a private beach! Three bedrooms await you near Shelter Island beaches! is a holiday home in Shelter Island, with easy beach access, parking, and kitchen access. This stay gives…

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About Relax at a private beach! Three bedrooms await you near Shelter Island beaches!

Relax at a private beach! Three bedrooms await you near Shelter Island beaches! is a holiday home in Shelter Island, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,716.

From$1,102/night

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Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock

Holiday Home, Shelter Island

Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock is a holiday home in Shelter Island, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock

Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock is a holiday home in Shelter Island, 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 $8,124.

From$1,161/night

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Vacation rentals with a pool in Shelter Island, NY

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

The Cliffside Resort Condominiums

Apartment, Shelter Island

The Cliffside Resort Condominiums is a apartment in Shelter Island, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Cliffside Resort Condominiums

The Cliffside Resort Condominiums is a apartment in Shelter Island, 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, free wifi, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,864.

From$695/night

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Beautiful Waterview Condo on the North Fork of LI

Condo, Shelter Island

Beautiful Waterview Condo on the North Fork of LI is a condo in Shelter Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Beautiful Waterview Condo on the North Fork of LI

Beautiful Waterview Condo on the North Fork of LI is a condo in Shelter Island, 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 $4,875.

From$696/night

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Gorgeous Shelter Island Retreat with Pool and Private Grounds

Holiday Home, Shelter Island

Gorgeous Shelter Island Retreat with Pool and Private Grounds is a holiday home in Shelter Island, with pet-friendly space, pool access, and a quieter setting. This stay gives travelers a…

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About Gorgeous Shelter Island Retreat with Pool and Private Grounds

Gorgeous Shelter Island Retreat with Pool and Private Grounds is a holiday home in Shelter Island, with pet-friendly space, pool access, and a quieter setting. 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $10,425.

From$1,489/night

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Brilliant 4-bedroom house with heated pool in charming Shelter Island

Holiday Home, Shelter Island

Brilliant 4-bedroom house with heated pool in charming Shelter Island is a holiday home in Shelter Island, with pool access and room for a group. This stay gives travelers a comfortable…

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About Brilliant 4-bedroom house with heated pool in charming Shelter Island

Brilliant 4-bedroom house with heated pool in charming Shelter Island is a holiday home in Shelter Island, with pool access 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, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $12,218.

From$1,745/night

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Vacation rentals with parking in Shelter Island, NY

Find vacation rentals that make arriving by car easier.

Cozy Ranch in Broadwaters Cove! Near beaches, boating and wineries!

Holiday Home, Shelter Island

Cozy Ranch in Broadwaters Cove! Near beaches, boating and wineries! is a holiday home in Shelter Island, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Cozy Ranch in Broadwaters Cove! Near beaches, boating and wineries!

Cozy Ranch in Broadwaters Cove! Near beaches, boating and wineries! is a holiday home in Shelter Island, 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: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,198.

From$314/night

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Renovated Townhouse walk to all

Holiday Home, Shelter Island

Renovated Townhouse walk to all is a holiday home in Shelter Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Renovated Townhouse walk to all

Renovated Townhouse walk to all is a holiday home in Shelter Island, 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 $4,748.

From$678/night

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Northfork Townhouse walk to all

Holiday Home, Shelter Island

Northfork Townhouse walk to all is a holiday home in Shelter Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Northfork Townhouse walk to all

Northfork Townhouse walk to all is a holiday home in Shelter Island, 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 $5,291.

From$756/night

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Family and Friends in Historic Greenport

Holiday Home, Shelter Island

Family and Friends in Historic Greenport is a holiday home in Shelter Island, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Family and Friends in Historic Greenport

Family and Friends in Historic Greenport is a holiday home in Shelter Island, with parking, kitchen access, 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: kitchen, with kitchen, kids friendly, kids friendly videos or books, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,855.

From$836/night

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Pet-friendly vacation rentals in Shelter Island, NY

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

North Fork Charmer with wrap-around deck & comfy living space. Pet-Friendly!

Holiday Home, Shelter Island

North Fork Charmer with wrap-around deck & comfy living space. Pet-Friendly! is a holiday home in Shelter Island, with pet-friendly space, outdoor space, and kitchen access. This stay gives…

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About North Fork Charmer with wrap-around deck & comfy living space. Pet-Friendly!

North Fork Charmer with wrap-around deck & comfy living space. Pet-Friendly! is a holiday home in Shelter Island, with pet-friendly space, outdoor 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 $4,197.

From$600/night

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Bright and Spacious Summer Home Steps from the Beach

Holiday Home, Shelter Island

Bright and Spacious Summer Home Steps from the Beach is a holiday home in Shelter Island, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a…

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About Bright and Spacious Summer Home Steps from the Beach

Bright and Spacious Summer Home Steps from the Beach is a holiday home in Shelter Island, with pet-friendly space, 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 cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,960.

From$851/night

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4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres

Holiday Home, Shelter Island

4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres is a holiday home in Shelter Island, with pet-friendly space, parking, and room for a group. This stay gives…

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About 4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres

4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres is a holiday home in Shelter Island, with pet-friendly space, 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, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,958.

From$994/night

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Newly renovated! Shelter Island Gem, 3 blocks from Sunset Beach

Holiday Home, Shelter Island

Newly renovated! Shelter Island Gem, 3 blocks from Sunset Beach is a holiday home in Shelter Island, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a…

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About Newly renovated! Shelter Island Gem, 3 blocks from Sunset Beach

Newly renovated! Shelter Island Gem, 3 blocks from Sunset Beach is a holiday home in Shelter Island, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,921.

From$1,417/night

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Vacation rentals with a kitchen in Shelter Island, NY

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

Charming Country Home sits on a 3-acre property in Bucolic Orient.

Holiday Home, Shelter Island

Charming Country Home sits on a 3-acre property in Bucolic Orient. is a holiday home in Shelter Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable…

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About Charming Country Home sits on a 3-acre property in Bucolic Orient.

Charming Country Home sits on a 3-acre property in Bucolic Orient. is a holiday home in Shelter Island, 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 $5,134.

From$733/night

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Beautiful Soundfront condominium

Condo, Shelter Island

Beautiful Soundfront condominium is a condo in Shelter Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Beautiful Soundfront condominium

Beautiful Soundfront condominium is a condo in Shelter Island, 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 $5,546.

From$792/night

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Relax in this light-filled home, steps from the beach and a short walk to town!

Holiday Home, Shelter Island

Relax in this light-filled home, steps from the beach and a short walk to town! is a holiday home in Shelter Island, with pet-friendly space, easy beach access, and kitchen access. This…

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About Relax in this light-filled home, steps from the beach and a short walk to town!

Relax in this light-filled home, steps from the beach and a short walk to town! is a holiday home in Shelter Island, with pet-friendly space, 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 cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,352.

From$1,336/night

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Away From it All! Bright, generous and well located 5-bedroom/3.5 Heights house

Holiday Home, Shelter Island

Away From it All! Bright, generous and well located 5-bedroom/3.5 Heights house is a holiday home in Shelter Island, with parking, kitchen access, and room for a group. This stay gives…

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About Away From it All! Bright, generous and well located 5-bedroom/3.5 Heights house

Away From it All! Bright, generous and well located 5-bedroom/3.5 Heights house is a holiday home in Shelter Island, with parking, kitchen access, 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: kitchen, with kitchen, gym, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $11,682.

From$1,669/night

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