Vacation rentals in Lewisboro, NY

Best vacation rentals and Airbnb offers in Lewisboro, NY

10 ★ 89 reviews

Enjoy our 3-story, family-friendly Carriage House Fireplace and outdoor fire pit

Guest House, Lewisboro

Enjoy our 3-story, family-friendly Carriage House Fireplace and outdoor fire pit is a guest house in Lewisboro, with kitchen access and room for a group. This stay gives travelers a…

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About Enjoy our 3-story, family-friendly Carriage House Fireplace and outdoor fire pit

Enjoy our 3-story, family-friendly Carriage House Fireplace and outdoor fire pit is a guest house in Lewisboro, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,256.

From$608/night

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10 ★ 21 reviews

Charming Cottage located on Historic Estate 1 Hour from NYC!

Guest House, Lewisboro

Charming Cottage located on Historic Estate 1 Hour from NYC! is a guest house in Lewisboro, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Charming Cottage located on Historic Estate 1 Hour from NYC!

Charming Cottage located on Historic Estate 1 Hour from NYC! is a guest house in Lewisboro, 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, gym, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,926.

From$418/night

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10 ★ 11 reviews

Modern & Serene 3 Bedroom Townhouse in SoNo

Holiday Home, Lewisboro

Modern & Serene 3 Bedroom Townhouse in SoNo is a holiday home in Lewisboro, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Modern & Serene 3 Bedroom Townhouse in SoNo

Modern & Serene 3 Bedroom Townhouse in SoNo is a holiday home in Lewisboro, 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 washer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,456.

From$351/night

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10 ★ 3 reviews

Pound Ridge Retreat: Private Trails, Fire Pit, Yoga + Fast Wi-Fi

Holiday Home, Lewisboro

Pound Ridge Retreat: Private Trails, Fire Pit, Yoga + Fast Wi-Fi is a holiday home in Lewisboro, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a…

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About Pound Ridge Retreat: Private Trails, Fire Pit, Yoga + Fast Wi-Fi

Pound Ridge Retreat: Private Trails, Fire Pit, Yoga + Fast Wi-Fi is a holiday home in Lewisboro, 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 cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $5,889.

From$841/night

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Family-friendly vacation rentals in Lewisboro, NY

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

10 ★ 1 reviews

Cozy 1-bedroom lakefront cottage on beautiful Lake Mahopac. Come enjoy!

Cottage, Lewisboro

Cozy 1-bedroom lakefront cottage on beautiful Lake Mahopac. Come enjoy! is a cottage in Lewisboro, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Cozy 1-bedroom lakefront cottage on beautiful Lake Mahopac. Come enjoy!

Cozy 1-bedroom lakefront cottage on beautiful Lake Mahopac. Come enjoy! is a cottage in Lewisboro, 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, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,398.

From$343/night

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Compo Beach access gated private house in Westport

Holiday Home, Lewisboro

Compo Beach access gated private house in Westport is a holiday home in Lewisboro, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable…

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About Compo Beach access gated private house in Westport

Compo Beach access gated private house in Westport is a holiday home in Lewisboro, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,961.

From$709/night

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Newly Renovated Charming Greenwich Guest Cottage

Cottage, Lewisboro

Newly Renovated Charming Greenwich Guest Cottage is a cottage in Lewisboro. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Newly Renovated Charming Greenwich Guest Cottage

Newly Renovated Charming Greenwich Guest Cottage is a cottage in Lewisboro. 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, washer, dryer, ac, and air conditioning.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $5,163.

From$738/night

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Sophisticated Country Living

Holiday Home, Lewisboro

Sophisticated Country Living is a holiday home in Lewisboro, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Sophisticated Country Living

Sophisticated Country Living is a holiday home in Lewisboro, 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, gym, and kids friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $10,032.

From$1,433/night

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Pet-friendly vacation rentals in Lewisboro, NY

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

9.8 ★ 14 reviews

Westport: Walk to Town, Private Natural Setting, Lovely Neighborhood

Holiday Home, Lewisboro

Westport: Walk to Town, Private Natural Setting, Lovely Neighborhood is a holiday home in Lewisboro, with pet-friendly space. This stay gives travelers a comfortable base for exploring the…

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About Westport: Walk to Town, Private Natural Setting, Lovely Neighborhood

Westport: Walk to Town, Private Natural Setting, Lovely Neighborhood is a holiday home in Lewisboro, with pet-friendly space. 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, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $5,513.

From$788/night

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9.6 ★ 4 reviews

Private Country Getaway

Holiday Home, Lewisboro

Private Country Getaway is a holiday home in Lewisboro, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Private Country Getaway

Private Country Getaway is a holiday home in Lewisboro, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $8,428.

From$1,204/night

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Lakefront House Rental for Summer

Holiday Home, Lewisboro

Lakefront House Rental for Summer is a holiday home in Lewisboro, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Lakefront House Rental for Summer

Lakefront House Rental for Summer is a holiday home in Lewisboro, 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 wifi, pet friendly, pets friendly, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $6,320.

From$903/night

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Amara Garden in New Canaan

Villa, Lewisboro

Amara Garden in New Canaan is a villa in Lewisboro, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Amara Garden in New Canaan

Amara Garden in New Canaan is a villa in Lewisboro, 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, hot tub, pet friendly, pets friendly, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $7,286.

From$1,041/night

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Vacation rentals with a pool in Lewisboro, NY

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

10 ★ 24 reviews

6 Bedroom Elegant and Comfy Upstate Oasis SANITIZED

Holiday Home, Lewisboro

6 Bedroom Elegant and Comfy Upstate Oasis SANITIZED is a holiday home in Lewisboro, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the…

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About 6 Bedroom Elegant and Comfy Upstate Oasis SANITIZED

6 Bedroom Elegant and Comfy Upstate Oasis SANITIZED is a holiday home in Lewisboro, with pool 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, pool, hot tub, and free wifi.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $13,006.

From$1,858/night

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10 ★ 7 reviews

MidCenturyMod spectacularly Renovated 1 LEVEL living paradise +EV charger

Holiday Home, Lewisboro

MidCenturyMod spectacularly Renovated 1 LEVEL living paradise +EV charger is a holiday home in Lewisboro, with pool access and kitchen access. This stay gives travelers a comfortable base…

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About MidCenturyMod spectacularly Renovated 1 LEVEL living paradise +EV charger

MidCenturyMod spectacularly Renovated 1 LEVEL living paradise +EV charger is a holiday home in Lewisboro, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,395.

From$628/night

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10 ★ 1 reviews

Gorgeous Westchester Home with Pool, Hot Tub, Steam Room & Tennis!

Holiday Home, Lewisboro

Gorgeous Westchester Home with Pool, Hot Tub, Steam Room & Tennis! is a holiday home in Lewisboro, with pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Gorgeous Westchester Home with Pool, Hot Tub, Steam Room & Tennis!

Gorgeous Westchester Home with Pool, Hot Tub, Steam Room & Tennis! is a holiday home in Lewisboro, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $23,254.

From$3,322/night

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9.8 ★ 6 reviews

Modern 4 bed 4.5 bath w hot tub & heated pool close to beach

Holiday Home, Lewisboro

Modern 4 bed 4.5 bath w hot tub & heated pool close to beach is a holiday home in Lewisboro, with pool access and easy beach access. This stay gives travelers a comfortable base for…

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About Modern 4 bed 4.5 bath w hot tub & heated pool close to beach

Modern 4 bed 4.5 bath w hot tub & heated pool close to beach is a holiday home in Lewisboro, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $9,646.

From$1,378/night

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Vacation rentals with parking in Lewisboro, NY

Find vacation rentals that make arriving by car easier.

10 ★ 12 reviews

Classic Rowayton Victorian, with a modern feel!

Holiday Home, Lewisboro

Classic Rowayton Victorian, with a modern feel! is a holiday home in Lewisboro, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Classic Rowayton Victorian, with a modern feel!

Classic Rowayton Victorian, with a modern feel! is a holiday home in Lewisboro, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $13,987.

From$1,998/night

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10 ★ 2 reviews

Interior Designer's Enchanting Home with Private Beach 1.5hrs from Brooklyn

Holiday Home, Lewisboro

Interior Designer's Enchanting Home with Private Beach 1.5hrs from Brooklyn is a holiday home in Lewisboro, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Interior Designer's Enchanting Home with Private Beach 1.5hrs from Brooklyn

Interior Designer's Enchanting Home with Private Beach 1.5hrs from Brooklyn is a holiday home in Lewisboro, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $11,165.

From$1,595/night

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9.2 ★ 10 reviews

Lake Mahopac House with lakefront & pontoon boat

Holiday Home, Lewisboro

Lake Mahopac House with lakefront & pontoon boat is a holiday home in Lewisboro, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Lake Mahopac House with lakefront & pontoon boat

Lake Mahopac House with lakefront & pontoon boat is a holiday home in Lewisboro, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $7,789.

From$1,113/night

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Summer by the Shore, Washington Street nightlife, MetroNorth 60 minutes to GCT

Holiday Home, Lewisboro

Summer by the Shore, Washington Street nightlife, MetroNorth 60 minutes to GCT is a holiday home in Lewisboro, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Summer by the Shore, Washington Street nightlife, MetroNorth 60 minutes to GCT

Summer by the Shore, Washington Street nightlife, MetroNorth 60 minutes to GCT is a holiday home in Lewisboro, 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 fireplace.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,180.

From$311/night

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Vacation rentals with a kitchen in Lewisboro, NY

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

10 ★ 3 reviews

Chic, Impeccably Decorated 5000 sq ft Estate, Coveted Greens Farms, 5 bed, 6 bth

Holiday Home, Lewisboro

Chic, Impeccably Decorated 5000 sq ft Estate, Coveted Greens Farms, 5 bed, 6 bth is a holiday home in Lewisboro, with pool access and kitchen access. This stay gives travelers a comfortable…

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About Chic, Impeccably Decorated 5000 sq ft Estate, Coveted Greens Farms, 5 bed, 6 bth

Chic, Impeccably Decorated 5000 sq ft Estate, Coveted Greens Farms, 5 bed, 6 bth is a holiday home in Lewisboro, 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, hot tub, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $17,529.

From$2,504/night

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10 ★ 1 reviews

Charming 3-bedroom house with AC and WiFi lower label muvie theater ,

Holiday Home, Lewisboro

Charming 3-bedroom house with AC and WiFi lower label muvie theater , is a holiday home in Lewisboro, with kitchen access and room for a group. This stay gives travelers a comfortable base…

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About Charming 3-bedroom house with AC and WiFi lower label muvie theater ,

Charming 3-bedroom house with AC and WiFi lower label muvie theater , is a holiday home in Lewisboro, 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, washer, and dryer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,314.

From$473/night

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Pet-Friendly 1BR Apartment with/Laundry- Walk to Shops and Downtown

Apartment, Lewisboro

Pet-Friendly 1BR Apartment with/Laundry- Walk to Shops and Downtown is a apartment in Lewisboro, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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About Pet-Friendly 1BR Apartment with/Laundry- Walk to Shops and Downtown

Pet-Friendly 1BR Apartment with/Laundry- Walk to Shops and Downtown is a apartment in Lewisboro, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,192.

From$170/night

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Tranquil Country Contemporary

Holiday Home, Lewisboro

Tranquil Country Contemporary is a holiday home in Lewisboro, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Tranquil Country Contemporary

Tranquil Country Contemporary is a holiday home in Lewisboro, 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, and internet.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,741.

From$677/night

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