Vacation rentals in Smithtown, NY

Best vacation rentals and Airbnb offers in Smithtown, NY

Charming Studio Close to Everything!

Apartment, Smithtown

Charming Studio Close to Everything! is a apartment in Smithtown, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Charming Studio Close to Everything!

Charming Studio Close to Everything! is a apartment in Smithtown, 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, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,032.

From$147/night

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Spacious one Bedroom Apt with private entrance

Apartment, Smithtown

Spacious one Bedroom Apt with private entrance is a apartment in Smithtown, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance is a apartment in Smithtown, with 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 cancellation, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,065.

From$152/night

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Adorable 1-bedroom house with AC in peaceful Selden neighborhood

Holiday Home, Smithtown

Adorable 1-bedroom house with AC in peaceful Selden neighborhood is a holiday home in Smithtown, with room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Adorable 1-bedroom house with AC in peaceful Selden neighborhood

Adorable 1-bedroom house with AC in peaceful Selden neighborhood is a holiday home in Smithtown, with 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, ac, air conditioning, heating, and non smoking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,145.

From$164/night

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Adorable 2-br apt Pet-Friendly .Fast WiFi .Near Airport & LIRR

Apartment, Smithtown

Adorable 2-br apt Pet-Friendly .Fast WiFi .Near Airport & LIRR is a apartment in Smithtown, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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About Adorable 2-br apt Pet-Friendly .Fast WiFi .Near Airport & LIRR

Adorable 2-br apt Pet-Friendly .Fast WiFi .Near Airport & LIRR is a apartment in Smithtown, with pet-friendly space, 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 cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,235.

From$176/night

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Vacation rentals with a pool in Smithtown, NY

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

Pool Oasis Big Yard 1 Bedroom + 1 Living room with SofaBed nearby Train to NYC

Country House, Smithtown

Pool Oasis Big Yard 1 Bedroom + 1 Living room with SofaBed nearby Train to NYC is a country house in Smithtown, with pool access, parking, and kitchen access. This stay gives travelers a…

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About Pool Oasis Big Yard 1 Bedroom + 1 Living room with SofaBed nearby Train to NYC

Pool Oasis Big Yard 1 Bedroom + 1 Living room with SofaBed nearby Train to NYC is a country house in Smithtown, with pool 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,381.

From$197/night

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1856 Trading House close to water

Condo, Smithtown

1856 Trading House close to water is a condo in Smithtown, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About 1856 Trading House close to water

1856 Trading House close to water is a condo in Smithtown, 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, pool, hot tub, and free wifi.

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

From$276/night

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Lovely escape, home away from home 10 mins from all beaches.

Holiday Home, Smithtown

Lovely escape, home away from home 10 mins from all beaches. is a holiday home in Smithtown, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base…

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About Lovely escape, home away from home 10 mins from all beaches.

Lovely escape, home away from home 10 mins from all beaches. is a holiday home in Smithtown, 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, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,214.

From$459/night

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Luxurious 4-bedroom house with an outdoor pool 25 mins from the Hamptons

Holiday Home, Smithtown

Luxurious 4-bedroom house with an outdoor pool 25 mins from the Hamptons is a holiday home in Smithtown, with pool access, parking, and kitchen access. This stay gives travelers a…

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About Luxurious 4-bedroom house with an outdoor pool 25 mins from the Hamptons

Luxurious 4-bedroom house with an outdoor pool 25 mins from the Hamptons is a holiday home in Smithtown, with pool 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,513.

From$788/night

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Vacation rentals with parking in Smithtown, NY

Find vacation rentals that make arriving by car easier.

Cozy 1-bedroom apt in superb West Babylon with WiFi, Central AC/Heat, 2nd Floor

Apartment, Smithtown

Cozy 1-bedroom apt in superb West Babylon with WiFi, Central AC/Heat, 2nd Floor is a apartment in Smithtown, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Cozy 1-bedroom apt in superb West Babylon with WiFi, Central AC/Heat, 2nd Floor

Cozy 1-bedroom apt in superb West Babylon with WiFi, Central AC/Heat, 2nd Floor is a apartment in Smithtown, 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, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,291.

From$184/night

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Private 1BR Apt • Peaceful Stay 1hr to NYC Great amenities - great town!

Apartment, Smithtown

Private 1BR Apt · Peaceful Stay 1hr to NYC Great amenities - great town! is a apartment in Smithtown, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Private 1BR Apt • Peaceful Stay 1hr to NYC Great amenities - great town!

Private 1BR Apt · Peaceful Stay 1hr to NYC Great amenities - great town! is a apartment in Smithtown, 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, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,295.

From$185/night

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Cozy Dix Hills Apt w/ Deck ~ 7 Mi to Beach!

Apartment, Smithtown

Cozy Dix Hills Apt w/ Deck ~ 7 Mi to Beach! is a apartment in Smithtown, with easy beach access, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the…

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About Cozy Dix Hills Apt w/ Deck ~ 7 Mi to Beach!

Cozy Dix Hills Apt w/ Deck ~ 7 Mi to Beach! is a apartment in Smithtown, with easy beach access, outdoor 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, free wifi, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,126.

From$214/night

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Lovely Basement with 2 Bedrooms and Kitchen

Holiday Home, Smithtown

Lovely Basement with 2 Bedrooms and Kitchen is a holiday home in Smithtown, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Lovely Basement with 2 Bedrooms and Kitchen

Lovely Basement with 2 Bedrooms and Kitchen is a holiday home in Smithtown, 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: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,865.

From$266/night

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Pet-friendly vacation rentals in Smithtown, NY

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

Private 1 bedroom apt in a quiet neighborhood, close to all!

Apartment, Smithtown

Private 1 bedroom apt in a quiet neighborhood, close to all! is a apartment in Smithtown, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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About Private 1 bedroom apt in a quiet neighborhood, close to all!

Private 1 bedroom apt in a quiet neighborhood, close to all! is a apartment in Smithtown, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,504.

From$215/night

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Modern 2BR Retreat w/ Full Kitchen & Living

Holiday Home, Smithtown

Modern 2BR Retreat w/ Full Kitchen & Living is a holiday home in Smithtown, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Modern 2BR Retreat w/ Full Kitchen & Living

Modern 2BR Retreat w/ Full Kitchen & Living is a holiday home in Smithtown, 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 $1,540.

From$220/night

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Bay Shore Vacation Rental ~ 7 Mi to the Beach

Holiday Home, Smithtown

Bay Shore Vacation Rental ~ 7 Mi to the Beach is a holiday home in Smithtown, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Bay Shore Vacation Rental ~ 7 Mi to the Beach

Bay Shore Vacation Rental ~ 7 Mi to the Beach is a holiday home in Smithtown, 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 $1,620.

From$231/night

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Private 3Br Apt: King-2Queen -PetPally -LTR-STR

Apartment, Smithtown

Private 3Br Apt: King-2Queen -PetPally -LTR-STR is a apartment in Smithtown, with pet-friendly space, parking, and room for a group. This stay gives travelers a comfortable base for…

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About Private 3Br Apt: King-2Queen -PetPally -LTR-STR

Private 3Br Apt: King-2Queen -PetPally -LTR-STR is a apartment in Smithtown, 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: parking, free parking, ac, air conditioning, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,796.

From$257/night

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Vacation rentals with a kitchen in Smithtown, NY

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

Newly done Cozy 1 bedroom basement apartment in Port Jefferson Station

Apartment, Smithtown

Newly done Cozy 1 bedroom basement apartment in Port Jefferson Station is a apartment in Smithtown, with kitchen access and room for a group. This stay gives travelers a comfortable base…

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About Newly done Cozy 1 bedroom basement apartment in Port Jefferson Station

Newly done Cozy 1 bedroom basement apartment in Port Jefferson Station is a apartment in Smithtown, with 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 cancellation, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,376.

From$197/night

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Cozy Dix Hills Apt w/ Deck ~ 7 Mi to Beach!

Apartment, Smithtown

Cozy Dix Hills Apt w/ Deck ~ 7 Mi to Beach! is a apartment in Smithtown, with easy beach access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Cozy Dix Hills Apt w/ Deck ~ 7 Mi to Beach!

Cozy Dix Hills Apt w/ Deck ~ 7 Mi to Beach! is a apartment in Smithtown, with easy beach access, 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,206.

From$250/night

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Cozy Dix Hills Apt w/ Deck ~ 7 Mi to Beach!

Apartment, Smithtown

Cozy Dix Hills Apt w/ Deck ~ 7 Mi to Beach! is a apartment in Smithtown, with easy beach access, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the…

Read more

About Cozy Dix Hills Apt w/ Deck ~ 7 Mi to Beach!

Cozy Dix Hills Apt w/ Deck ~ 7 Mi to Beach! is a apartment in Smithtown, with easy beach access, outdoor 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,956.

From$279/night

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Bay Shore Vacation Rental w/ Shared Yard!

Apartment, Smithtown

Bay Shore Vacation Rental w/ Shared Yard! is a apartment in Smithtown, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Bay Shore Vacation Rental w/ Shared Yard!

Bay Shore Vacation Rental w/ Shared Yard! is a apartment in Smithtown, 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 $3,127.

From$356/night

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Family-friendly vacation rentals in Smithtown, NY

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

Bay Shore Vacation Rental ~ 7 Mi to the Beach

Cottage, Smithtown

Bay Shore Vacation Rental ~ 7 Mi to the Beach is a cottage in Smithtown, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Bay Shore Vacation Rental ~ 7 Mi to the Beach

Bay Shore Vacation Rental ~ 7 Mi to the Beach is a cottage in Smithtown, 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 $2,003.

From$234/night

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Charming Stony Brook Cottage. Walk to village, marina, sand st. beach& Stony U.

Cottage, Smithtown

Charming Stony Brook Cottage. Walk to village, marina, sand st. beach& Stony U. is a cottage in Smithtown, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Charming Stony Brook Cottage. Walk to village, marina, sand st. beach& Stony U.

Charming Stony Brook Cottage. Walk to village, marina, sand st. beach& Stony U. is a cottage in Smithtown, 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 $1,950.

From$279/night

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Charming newly renovated 2-bedroom cottage with WiFi, AC,Parking spot Huntington

Cottage, Smithtown

Charming newly renovated 2-bedroom cottage with WiFi, AC,Parking spot Huntington is a cottage in Smithtown, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Charming newly renovated 2-bedroom cottage with WiFi, AC,Parking spot Huntington

Charming newly renovated 2-bedroom cottage with WiFi, AC,Parking spot Huntington is a cottage in Smithtown, 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: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,800.

From$543/night

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Spacious Gorgeous Getaway perfect for family reunion or business

Holiday Home, Smithtown

Spacious Gorgeous Getaway perfect for family reunion or business is a holiday home in Smithtown, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About Spacious Gorgeous Getaway perfect for family reunion or business

Spacious Gorgeous Getaway perfect for family reunion or business is a holiday home in Smithtown, with 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: hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,754.

From$1,108/night

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