Vacation rentals in Shelter Island Heights, NY

Best Vacation rentals and Airbnb offers in Shelter Island Heights, NY

NEWLY Renovated Family Home Great Area - Beach - Greenport - Ferry - Restaurants

Apartment, Shelter Island Heights

NEWLY Renovated Family Home Great Area - Beach - Greenport - Ferry - Restaurants is a apartment in Shelter Island Heights, with easy beach access, kitchen access, and room for a group. This…

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About NEWLY Renovated Family Home Great Area - Beach - Greenport - Ferry - Restaurants

NEWLY Renovated Family Home Great Area - Beach - Greenport - Ferry - Restaurants is a apartment in Shelter Island Heights, with easy beach access, 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,760.

From$281/night

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North Beach Fork Beach House

Holiday Home, Shelter Island Heights

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

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About North Beach Fork Beach House

North Beach Fork Beach House is a holiday home in Shelter Island Heights, 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 $3,263.

From$343/night

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

Cottage, Shelter Island Heights

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

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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 Heights, 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 $3,497.

From$350/night

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The Shoals Suites & Slips

Apartment, Shelter Island Heights

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

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About The Shoals Suites & Slips

The Shoals Suites & Slips is a apartment in Shelter Island Heights, 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 $2,983.

From$373/night

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Browse Waterfront Vacation Rentals in Shelter Island Heights, NY

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

Southold retreat-- Indoor/outdoor living near immaculate beaches & wineries

Holiday Home, Shelter Island Heights

Southold retreat-- Indoor/outdoor living near immaculate beaches & wineries is a holiday home in Shelter Island Heights, with easy beach access, parking, and kitchen access. This stay gives…

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About Southold retreat-- Indoor/outdoor living near immaculate beaches & wineries

Southold retreat-- Indoor/outdoor living near immaculate beaches & wineries is a holiday home in Shelter Island Heights, 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 $4,111.

From$414/night

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Waterfront Hot Tub Retreat w Kayaks | Kayak Point

Holiday Home, Shelter Island Heights

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

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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 Heights, 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 $5,802.

From$524/night

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The Cliffside Resort Condominiums

Apartment, Shelter Island Heights

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

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About The Cliffside Resort Condominiums

The Cliffside Resort Condominiums is a apartment in Shelter Island Heights, 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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Bright and Spacious Summer Home Steps from the Beach

Holiday Home, Shelter Island Heights

Bright and Spacious Summer Home Steps from the Beach is a holiday home in Shelter Island Heights, 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 Heights, 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 $6,864.

From$723/night

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Browse Vacation Rentals with a Pool in Shelter Island Heights, NY

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

Beautiful Waterview Condo on the North Fork of LI

Condo, Shelter Island Heights

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

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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 Heights, 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 $5,569.

From$590/night

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Beautiful Soundfront condominium

Condo, Shelter Island Heights

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

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About Beautiful Soundfront condominium

Beautiful Soundfront condominium is a condo in Shelter Island Heights, 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 $6,336.

From$675/night

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Harbor Knoll Bed & Breakfast

B & B, Shelter Island Heights

Harbor Knoll Bed & Breakfast is a b & b in Shelter Island Heights, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Harbor Knoll Bed & Breakfast

Harbor Knoll Bed & Breakfast is a b & b in Shelter Island Heights, 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: free cancellation, free breakfast, pool, free wifi, and beachfront.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,242.

From$655/night

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Harbor Knoll Bed and Breakfast

B & B, Shelter Island Heights

Harbor Knoll Bed and Breakfast is a b & b in Shelter Island Heights, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Harbor Knoll Bed and Breakfast

Harbor Knoll Bed and Breakfast is a b & b in Shelter Island Heights, 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, free breakfast, pool, free wifi, and for couples.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,890.

From$655/night

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Best Shelter Island Heights, NY vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Renovated Townhouse walk to all

Holiday Home, Shelter Island Heights

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

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About Renovated Townhouse walk to all

Renovated Townhouse walk to all is a holiday home in Shelter Island Heights, 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 $5,585.

From$588/night

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Northfork Townhouse walk to all

Holiday Home, Shelter Island Heights

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

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About Northfork Townhouse walk to all

Northfork Townhouse walk to all is a holiday home in Shelter Island Heights, 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 $6,020.

From$636/night

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Family and Friends in Historic Greenport

Holiday Home, Shelter Island Heights

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

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About Family and Friends in Historic Greenport

Family and Friends in Historic Greenport is a holiday home in Shelter Island Heights, 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 $6,689.

From$714/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 Heights

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

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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 Heights, 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 $7,472.

From$815/night

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Best Pet-Friendly Vacation Rentals in Shelter Island Heights, NY

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

2 Bedroom Apartment in Historic Home with private yard

Apartment, Shelter Island Heights

2 Bedroom Apartment in Historic Home with private yard is a apartment in Shelter Island Heights, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About 2 Bedroom Apartment in Historic Home with private yard

2 Bedroom Apartment in Historic Home with private yard is a apartment in Shelter Island Heights, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,217.

From$352/night

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Historic 2-bedroom upstairs apartment close to beaches, town and vineyards.

Holiday Home, Shelter Island Heights

Historic 2-bedroom upstairs apartment close to beaches, town and vineyards. is a holiday home in Shelter Island Heights, with pet-friendly space, easy beach access, and kitchen access. This…

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About Historic 2-bedroom upstairs apartment close to beaches, town and vineyards.

Historic 2-bedroom upstairs apartment close to beaches, town and vineyards. is a holiday home in Shelter Island Heights, 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 $3,518.

From$386/night

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

Holiday Home, Shelter Island Heights

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

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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 Heights, 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 $4,743.

From$479/night

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Shelter Island Retreat, 5 bdrms near everything!

Holiday Home, Shelter Island Heights

Shelter Island Retreat, 5 bdrms near everything! is a holiday home in Shelter Island Heights, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a…

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About Shelter Island Retreat, 5 bdrms near everything!

Shelter Island Retreat, 5 bdrms near everything! is a holiday home in Shelter Island Heights, with pet-friendly space, kitchen 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,119.

From$713/night

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Best Shelter Island Heights, NY vacation rentals with a kitchen

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

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

Holiday Home, Shelter Island Heights

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

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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 Heights, 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 $8,816.

From$890/night

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Shelter Island, Waterfront, Lazy Days With Stunning Views

Holiday Home, Shelter Island Heights

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

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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 Heights, 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 $8,586.

From$914/night

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

Holiday Home, Shelter Island Heights

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

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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 Heights, 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 $9,281.

From$983/night

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

Holiday Home, Shelter Island Heights

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

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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 Heights, 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 $11,335.

From$1,250/night

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