Vacation rentals in Orient Point, NY

Best vacation rentals and Airbnb offers in Orient Point, NY

Saybrook Point Cottage - Charming and Private

Cottage, Orient Point

Saybrook Point Cottage - Charming and Private is a cottage in Orient Point, 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 Orient Point, 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

Apartment, Orient Point

The Nest at Black Hall is a apartment in Orient Point, 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 Orient Point, 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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Giants Neck Heights. Booking Fall 2025!

Holiday Home, Orient Point

Giants Neck Heights. Booking Fall 2025! is a holiday home in Orient Point, 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 Orient Point, 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 Anchor at Soundview · Beach+Ocean+Sunrise

Apartment, Orient Point

The Anchor at Soundview · Beach+Ocean+Sunrise is a apartment in Orient Point, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area,…

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About The Anchor at Soundview · Beach+Ocean+Sunrise

The Anchor at Soundview · Beach+Ocean+Sunrise is a apartment in Orient Point, with easy beach 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: free cancellation, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,932.

From$276/night

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Vacation rentals with a pool in Orient Point, NY

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

East Hampton Art House Bed and Breakfast

B & B, Orient Point

East Hampton Art House Bed and Breakfast is a b & b in Orient Point, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About East Hampton Art House Bed and Breakfast

East Hampton Art House Bed and Breakfast is a b & b in Orient Point, 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 breakfast, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $14,008.

From$1,753/night

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Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve

Holiday Home, Orient Point

Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve is a holiday home in Orient Point, with pool access, easy beach access, and parking. This stay gives travelers a…

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About Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve

Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve is a holiday home in Orient Point, with pool access, easy beach 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,215.

From$745/night

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Perfect Family Summer Vacation Home Close to beach 18x42 pool

Holiday Home, Orient Point

Perfect Family Summer Vacation Home Close to beach 18x42 pool is a holiday home in Orient Point, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a…

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About Perfect Family Summer Vacation Home Close to beach 18x42 pool

Perfect Family Summer Vacation Home Close to beach 18x42 pool is a holiday home in Orient Point, 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,697.

From$814/night

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Private Beach and Ing Pool! New build 4 bed 4.5 bth Farmhouse! Chefs kitchen

Country House, Orient Point

Private Beach and Ing Pool! New build 4 bed 4.5 bth Farmhouse! Chefs kitchen is a country house in Orient Point, with pool access, easy beach access, and kitchen access. This stay gives…

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About Private Beach and Ing Pool! New build 4 bed 4.5 bth Farmhouse! Chefs kitchen

Private Beach and Ing Pool! New build 4 bed 4.5 bth Farmhouse! Chefs kitchen is a country house in Orient Point, with pool access, 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, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $15,225.

From$2,175/night

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Vacation rentals with parking in Orient Point, NY

Find vacation rentals that make arriving by car easier.

Keel at Soundview · Beach+OceanView+Sunrise

Apartment, Orient Point

Keel at Soundview · Beach+OceanView+Sunrise is a apartment in Orient Point, 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 Orient Point, 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 $2,367.

From$338/night

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Forecastle at Soundview · Beach+OceanView+Sunrise

Apartment, Orient Point

Forecastle at Soundview · Beach+OceanView+Sunrise is a apartment in Orient Point, 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 Orient Point, 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 $2,512.

From$359/night

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Inn at Harbor Hill Marina

B & B, Orient Point

Inn at Harbor Hill Marina is a b & b in Orient Point, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Inn at Harbor Hill Marina

Inn at Harbor Hill Marina is a b & b in Orient Point, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free breakfast, free wifi, for couples, wine or champagne, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,408.

From$299/night

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Inn at Harbor Hill Marina

B & B, Orient Point

Inn at Harbor Hill Marina is a b & b in Orient Point, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Inn at Harbor Hill Marina

Inn at Harbor Hill Marina is a b & b in Orient Point, with parking. 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, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,408.

From$299/night

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Pet-friendly vacation rentals in Orient Point, NY

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

Now available for short term rentals during the off season.

Holiday Home, Orient Point

Now available for short term rentals during the off season. is a holiday home in Orient Point, 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 Orient Point, 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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Your Nest Near The Beach

Holiday Home, Orient Point

Your Nest Near The Beach is a holiday home in Orient Point, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Your Nest Near The Beach

Your Nest Near The Beach is a holiday home in Orient Point, 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 $3,160.

From$451/night

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Relaxing Private Retreat Near Preserve. Pets Welcome!

Holiday Home, Orient Point

Relaxing Private Retreat Near Preserve. Pets Welcome! is a holiday home in Orient Point, with pet-friendly space and a quieter setting. This stay gives travelers a comfortable base for…

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About Relaxing Private Retreat Near Preserve. Pets Welcome!

Relaxing Private Retreat Near Preserve. Pets Welcome! is a holiday home in Orient Point, with pet-friendly space 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 $3,521.

From$503/night

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

Holiday Home, Orient Point

North Fork Charmer with wrap-around deck & comfy living space. Pet-Friendly! is a holiday home in Orient Point, 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 Orient Point, 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 $4,152.

From$593/night

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Vacation rentals with a kitchen in Orient Point, NY

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

The Bay Cottage · Rocky Neck Park, Beach & Niantic

Holiday Home, Orient Point

The Bay Cottage · Rocky Neck Park, Beach & Niantic is a holiday home in Orient Point, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic is a holiday home in Orient Point, 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 $2,571.

From$367/night

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Beautiful Spacious Studio in a Beach Community

Apartment, Orient Point

Beautiful Spacious Studio in a Beach Community is a apartment in Orient Point, 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 Orient Point, 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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Stay just steps away from a beautiful private beach in Old Lyme!

Cottage, Orient Point

Stay just steps away from a beautiful private beach in Old Lyme! is a cottage in Orient Point, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable…

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About Stay just steps away from a beautiful private beach in Old Lyme!

Stay just steps away from a beautiful private beach in Old Lyme! is a cottage in Orient Point, 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 $2,795.

From$399/night

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Private cottage with WiFi in charming Old Lyme Shores Beach Association

Cottage, Orient Point

Private cottage with WiFi in charming Old Lyme Shores Beach Association is a cottage in Orient Point, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Private cottage with WiFi in charming Old Lyme Shores Beach Association

Private cottage with WiFi in charming Old Lyme Shores Beach Association is a cottage in Orient Point, 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 $3,095.

From$442/night

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Family-friendly vacation rentals in Orient Point, NY

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

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

Cottage, Orient Point

Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach is a cottage in Orient Point, 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 Orient Point, 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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2Bdr Beachfront; 11B second floor, Old Colony Beach , CT

Cottage, Orient Point

2Bdr Beachfront; 11B second floor, Old Colony Beach , CT is a cottage in Orient Point, 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 Orient Point, 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

Cottage, Orient Point

Cozy/comfy/peaceful beach home is a cottage in Orient Point, 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 Orient Point, 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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Charming, Renovated Island Cottage - Shelter Island License #: 012-2017

Cottage, Orient Point

Charming, Renovated Island Cottage - Shelter Island License #: 012-2017 is a cottage in Orient Point, 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 Orient Point, 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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