Vacation rentals in Southold, NY

94 available vacation rental offers

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Best vacation rentals and Airbnb offers in Southold, NY

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

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

Holiday Home, Southold

Cozy Ranch in Broadwaters Cove! Near beaches, boating and wineries! is a holiday home in Southold, 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 Southold, 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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The Shoals Suites & Slips - Southold, NY

The Shoals Suites & Slips

Apartment, Southold

The Shoals Suites & Slips is a apartment in Southold, 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 Shoals Suites & Slips

The Shoals Suites & Slips is a apartment in Southold, 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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North Beach Fork Beach House - Southold, NY

North Beach Fork Beach House

Holiday Home, Southold

North Beach Fork Beach House is a holiday home in Southold, 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 Southold, 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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Relaxing Private Retreat Near Preserve. Pets Welcome! - Southold, NY

Relaxing Private Retreat Near Preserve. Pets Welcome!

Holiday Home, Southold

Relaxing Private Retreat Near Preserve. Pets Welcome! is a holiday home in Southold, 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 Southold, 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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Vacation rentals with a pool in Southold, 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 - Southold, NY

Beautiful Waterview Condo on the North Fork of LI

Condo, Southold

Beautiful Waterview Condo on the North Fork of LI is a condo in Southold, 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 Southold, 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 - Southold, NY

Beautiful Soundfront condominium

Condo, Southold

Beautiful Soundfront condominium is a condo in Southold, 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 Southold, 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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Southold Escape with Large Saltwater Pool on Wine Trail - Southold, NY

Southold Escape with Large Saltwater Pool on Wine Trail

Holiday Home, Southold

Southold Escape with Large Saltwater Pool on Wine Trail is a holiday home in Southold, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Southold Escape with Large Saltwater Pool on Wine Trail

Southold Escape with Large Saltwater Pool on Wine Trail is a holiday home in Southold, 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: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,247.

From$1,178/night
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Unique Southold waterfront luxury home with heated pool on Long Creek - Southold, NY

Unique Southold waterfront luxury home with heated pool on Long Creek

Holiday Home, Southold

Unique Southold waterfront luxury home with heated pool on Long Creek is a holiday home in Southold, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Unique Southold waterfront luxury home with heated pool on Long Creek

Unique Southold waterfront luxury home with heated pool on Long Creek is a holiday home in Southold, 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $10,419.

From$1,488/night
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Vacation rentals with parking in Southold, NY

Find vacation rentals that make arriving by car easier.

Charming Accommodations in the Hamptons - Southold, NY

Charming Accommodations in the Hamptons

Apartment, Southold

Charming Accommodations in the Hamptons is a apartment in Southold, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons is a apartment in Southold, with pet-friendly space 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, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,295.

From$614/night
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Renovated Townhouse walk to all - Southold, NY

Renovated Townhouse walk to all

Holiday Home, Southold

Renovated Townhouse walk to all is a holiday home in Southold, 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 Southold, 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 - Southold, NY

Northfork Townhouse walk to all

Holiday Home, Southold

Northfork Townhouse walk to all is a holiday home in Southold, 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 Southold, 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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Beautiful charming 1930s fully renovated cottage walking distance to the beach! - Southold, NY

Beautiful charming 1930s fully renovated cottage walking distance to the beach!

Cottage, Southold

Beautiful charming 1930s fully renovated cottage walking distance to the beach! is a cottage in Southold, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Beautiful charming 1930s fully renovated cottage walking distance to the beach!

Beautiful charming 1930s fully renovated cottage walking distance to the beach! is a cottage in Southold, 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 $5,558.

From$794/night
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Pet-friendly vacation rentals in Southold, NY

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

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

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

Holiday Home, Southold

North Fork Charmer with wrap-around deck & comfy living space. Pet-Friendly! is a holiday home in Southold, 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 Southold, 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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Waterfront North Fork Retreat • Sunsets, Beaches & Vineyards - Southold, NY

Waterfront North Fork Retreat • Sunsets, Beaches & Vineyards

Holiday Home, Southold

Waterfront North Fork Retreat · Sunsets, Beaches & Vineyards is a holiday home in Southold, with pet-friendly space, easy beach access, and a quieter setting. This stay gives travelers a…

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About Waterfront North Fork Retreat • Sunsets, Beaches & Vineyards

Waterfront North Fork Retreat · Sunsets, Beaches & Vineyards is a holiday home in Southold, with pet-friendly space, easy beach 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, gym, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,811.

From$1,116/night
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Relax in this light-filled home, steps from the beach and a short walk to town! - Southold, NY

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

Holiday Home, Southold

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

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

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

Holiday Home, Southold

Newly renovated! Shelter Island Gem, 3 blocks from Sunset Beach is a holiday home in Southold, 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 Southold, 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 Southold, NY

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

Historic Renovated Farmhouse, 2min to Beach, Vineyards, Fireplace, Kid Friendly - Southold, NY

Historic Renovated Farmhouse, 2min to Beach, Vineyards, Fireplace, Kid Friendly

Holiday Home, Southold

Historic Renovated Farmhouse, 2min to Beach, Vineyards, Fireplace, Kid Friendly is a holiday home in Southold, with easy beach access and kitchen access. This stay gives travelers a…

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About Historic Renovated Farmhouse, 2min to Beach, Vineyards, Fireplace, Kid Friendly

Historic Renovated Farmhouse, 2min to Beach, Vineyards, Fireplace, Kid Friendly is a holiday home in Southold, 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: kitchen, with kitchen, gym, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,777.

From$825/night
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Family and Friends in Historic Greenport - Southold, NY

Family and Friends in Historic Greenport

Holiday Home, Southold

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

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About Family and Friends in Historic Greenport

Family and Friends in Historic Greenport is a holiday home in Southold, 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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Gorgeous Historical 6 bdrm House close to vineyards and breweries, - Southold, NY

Gorgeous Historical 6 bdrm House close to vineyards and breweries,

Holiday Home, Southold

Gorgeous Historical 6 bdrm House close to vineyards and breweries, is a holiday home in Southold, with kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Gorgeous Historical 6 bdrm House close to vineyards and breweries,

Gorgeous Historical 6 bdrm House close to vineyards and breweries, is a holiday home in Southold, with 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,072.

From$867/night
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Shelter Island, Waterfront, Lazy Days With Stunning Views - Southold, NY

Shelter Island, Waterfront, Lazy Days With Stunning Views

Holiday Home, Southold

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

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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 Southold, 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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Family-friendly vacation rentals in Southold, NY

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

Restored Seaport Village Cottage - Southold, NY

Restored Seaport Village Cottage

Cottage, Southold

Restored Seaport Village Cottage is a cottage in Southold, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Restored Seaport Village Cottage

Restored Seaport Village Cottage is a cottage in Southold, with 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,768.

From$681/night
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North Fork Resort - Southold, NY

North Fork Resort

Cottage, Southold

North Fork Resort is a cottage in Southold, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About North Fork Resort

North Fork Resort is a cottage in Southold, with pet-friendly space, 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: free cancellation, pool, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,642.

From$705/night
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Family friendly house with pool & walk to the beach in the heart of NOFO - Southold, NY

Family friendly house with pool & walk to the beach in the heart of NOFO

Holiday Home, Southold

Family friendly house with pool & walk to the beach in the heart of NOFO is a holiday home in Southold, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Family friendly house with pool & walk to the beach in the heart of NOFO

Family friendly house with pool & walk to the beach in the heart of NOFO is a holiday home in Southold, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,309.

From$758/night
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Family Beach House on the North Fork of Long Island - Southold, NY

Family Beach House on the North Fork of Long Island

Holiday Home, Southold

Family Beach House on the North Fork of Long Island is a holiday home in Southold, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable…

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About Family Beach House on the North Fork of Long Island

Family Beach House on the North Fork of Long Island is a holiday home in Southold, 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 $5,721.

From$817/night
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