Vacation rentals in Orient, NY

Best vacation rentals and Airbnb offers in Orient, NY

Saybrook Point Cottage - Charming and Private

Cottage, Orient

Saybrook Point Cottage - Charming and Private is a cottage in Orient, 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, 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 Anchor at Soundview · Beach+Ocean+Sunrise

Apartment, Orient

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

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About The Anchor at Soundview · Beach+Ocean+Sunrise

The Anchor at Soundview · Beach+Ocean+Sunrise is a apartment in Orient, 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 $1,924.

From$275/night

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Long Island Sound Studio

Apartment, Orient

Long Island Sound Studio is a apartment in Orient, 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 Long Island Sound Studio

Long Island Sound Studio is a apartment in Orient, 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 $2,020.

From$289/night

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Freeboard at Soundview · Beach+Ocean+Sunrise

Apartment, Orient

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

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About Freeboard at Soundview · Beach+Ocean+Sunrise

Freeboard at Soundview · Beach+Ocean+Sunrise is a apartment in Orient, 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 $2,151.

From$307/night

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Vacation rentals with a pool in Orient, NY

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

The Cliffside Resort Condominiums

Apartment, Orient

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

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About The Cliffside Resort Condominiums

The Cliffside Resort Condominiums is a apartment in Orient, 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, Orient

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

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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 Orient, 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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Beautiful Soundfront condominium

Condo, Orient

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

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About Beautiful Soundfront condominium

Beautiful Soundfront condominium is a condo in Orient, 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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Orient Point Waterfront Home – Private Beach & Stunning Views

Holiday Home, Orient

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

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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 Orient, 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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Vacation rentals with parking in Orient, NY

Find vacation rentals that make arriving by car easier.

Giants Neck Heights. Booking Fall 2025!

Holiday Home, Orient

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

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About Giants Neck Heights. Booking Fall 2025!

Giants Neck Heights. Booking Fall 2025! is a holiday home in Orient, 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

Apartment, Orient

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

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About The Mast at Soundview · Beach+Ocean+Sunrise

The Mast at Soundview · Beach+Ocean+Sunrise is a apartment in Orient, 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 $2,151.

From$307/night

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The Rudder at Soundview · Beach+Ocean+Sunrise

Apartment, Orient

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

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About The Rudder at Soundview · Beach+Ocean+Sunrise

The Rudder at Soundview · Beach+Ocean+Sunrise is a apartment in Orient, 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 $2,151.

From$307/night

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The Stern at Soundview · Beach+Ocean+Sunrise

Apartment, Orient

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

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About The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise is a apartment in Orient, 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 $2,151.

From$307/night

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Pet-friendly vacation rentals in Orient, 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

Now available for short term rentals during the off season. is a holiday home in Orient, 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, 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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Perfect Family Summer Vacation Home Close to beach 18x42 pool

Holiday Home, Orient

Perfect Family Summer Vacation Home Close to beach 18x42 pool is a holiday home in Orient, 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, 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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Bright and Spacious Summer Home Steps from the Beach

Holiday Home, Orient

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

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

Holiday Home, Orient

Private Vineyard Estate in Orient Village w Pool / AC / Walk to Beach & Town is a holiday home in Orient, 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 Orient, 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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Vacation rentals with a kitchen in Orient, NY

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

Keel at Soundview · Beach+OceanView+Sunrise

Apartment, Orient

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

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About Keel at Soundview · Beach+OceanView+Sunrise

Keel at Soundview · Beach+OceanView+Sunrise is a apartment in Orient, 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 $2,355.

From$336/night

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Cozy/comfy/peaceful beach home

Cottage, Orient

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

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About Cozy/comfy/peaceful beach home

Cozy/comfy/peaceful beach home is a cottage in Orient, 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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Forecastle at Soundview · Beach+OceanView+Sunrise

Apartment, Orient

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

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About Forecastle at Soundview · Beach+OceanView+Sunrise

Forecastle at Soundview · Beach+OceanView+Sunrise is a apartment in Orient, 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 $2,504.

From$358/night

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Beautiful Spacious Studio in a Beach Community

Apartment, Orient

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

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About Beautiful Spacious Studio in a Beach Community

Beautiful Spacious Studio in a Beach Community is a apartment in Orient, 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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Family-friendly vacation rentals in Orient, 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

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

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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, 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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Family Friendly, Beach Themed Cottage - Chalker Beach

Cottage, Orient

Family Friendly, Beach Themed Cottage - Chalker Beach is a cottage in Orient, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Family Friendly, Beach Themed Cottage - Chalker Beach

Family Friendly, Beach Themed Cottage - Chalker Beach is a cottage in Orient, 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: free wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,208.

From$315/night

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

Cottage, Orient

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

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

Cottage, Orient

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

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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, 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 $2,399.

From$343/night

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