Vacation rentals in Lewisboro, NY

47 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Lewisboro, NY

Fully Furnished in-law suite. Patio, Yard. Washer drier all private.Per friendly - Lewisboro, NY

Fully Furnished in-law suite. Patio, Yard. Washer drier all private.Per friendly

Apartment, Lewisboro

Fully Furnished in-law suite. Patio, Yard. Washer drier all private.Per friendly is a apartment in Lewisboro, with pet-friendly space and outdoor space. This stay gives travelers a…

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About Fully Furnished in-law suite. Patio, Yard. Washer drier all private.Per friendly

Fully Furnished in-law suite. Patio, Yard. Washer drier all private.Per friendly is a apartment in Lewisboro, with pet-friendly space and outdoor 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, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $612.

From$65/night
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Charming 1-bedroom apartment in Carmel with WiFi, AC - Lewisboro, NY

Charming 1-bedroom apartment in Carmel with WiFi, AC

Apartment, Lewisboro

Charming 1-bedroom apartment in Carmel with WiFi, AC is a apartment in Lewisboro, with pool access, parking, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC is a apartment in Lewisboro, with pool access, 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: pool, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,189.

From$128/night
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Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility. - Lewisboro, NY

Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility.

Apartment, Lewisboro

Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility. is a apartment in Lewisboro, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility.

Cozy ground floor suite ideal for a relaxing stay. Enjoy peace and tranquility. is a apartment in Lewisboro, with parking, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,299.

From$147/night
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Studio Flat Above Historic Cider Mill - Lewisboro, NY

Studio Flat Above Historic Cider Mill

Apartment, Lewisboro

Studio Flat Above Historic Cider Mill is a apartment in Lewisboro, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Studio Flat Above Historic Cider Mill

Studio Flat Above Historic Cider Mill is a apartment 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: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,630.

From$160/night
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Browse 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.

Serene 2-bedroom spacious apartment - Lewisboro, NY

Serene 2-bedroom spacious apartment

Apartment, Lewisboro

Serene 2-bedroom spacious apartment is a apartment in Lewisboro, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Serene 2-bedroom spacious apartment

Serene 2-bedroom spacious apartment is a apartment in Lewisboro, 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 $1,527.

From$166/night
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Guest House at Norwalk Inn - Lewisboro, NY

Guest House at Norwalk Inn

Guest House, Lewisboro

Guest House at Norwalk Inn is a guest house in Lewisboro, 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 Guest House at Norwalk Inn

Guest House at Norwalk Inn is a guest house 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, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,292.

From$409/night
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Modern 4 bed 4.5 bath w hot tub & heated pool close to beach - Lewisboro, NY

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $11,578.

From$1,250/night
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6 Bedroom Elegant and Comfy Upstate Oasis SANITIZED - Lewisboro, NY

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $12,120.

From$1,346/night
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Best Lewisboro, NY vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Welcome to Hat City Danbury | A Suburban Retreat Close to It All - Lewisboro, NY

Welcome to Hat City Danbury | A Suburban Retreat Close to It All

Apartment, Lewisboro

Welcome to Hat City Danbury · A Suburban Retreat Close to It All is a apartment in Lewisboro, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable…

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About Welcome to Hat City Danbury | A Suburban Retreat Close to It All

Welcome to Hat City Danbury · A Suburban Retreat Close to It All is a apartment in Lewisboro, with parking, 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, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,808.

From$188/night
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Summer by the Shore, Washington Street nightlife, MetroNorth 60 minutes to GCT - Lewisboro, NY

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,407.

From$240/night
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Designer Treehouse with Spa Bath - Lewisboro, NY

Designer Treehouse with Spa Bath

Apartment, Lewisboro

Designer Treehouse with Spa Bath is a apartment in Lewisboro, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Designer Treehouse with Spa Bath

Designer Treehouse with Spa Bath is a apartment 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,932.

From$415/night
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Darien family home on a Cul de Sac with pond. - Lewisboro, NY

Darien family home on a Cul de Sac with pond.

Holiday Home, Lewisboro

Darien family home on a Cul de Sac with pond. 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 Darien family home on a Cul de Sac with pond.

Darien family home on a Cul de Sac with pond. 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: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,547.

From$675/night
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Best Pet-Friendly Vacation Rentals in Lewisboro, NY

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

Bright and cheery summer retreat. Close to Compo, Saugatuck dining, and town. - Lewisboro, NY

Bright and cheery summer retreat. Close to Compo, Saugatuck dining, and town.

Holiday Home, Lewisboro

Bright and cheery summer retreat. Close to Compo, Saugatuck dining, and town. is a holiday home in Lewisboro, with pet-friendly space, kitchen access, and a quieter setting. This stay gives…

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About Bright and cheery summer retreat. Close to Compo, Saugatuck dining, and town.

Bright and cheery summer retreat. Close to Compo, Saugatuck dining, and town. 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: hot tub, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,116.

From$425/night
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Westport: Walk to Town, Private Natural Setting, Lovely Neighborhood - Lewisboro, NY

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,359.

From$663/night
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Lakefront House Rental for Summer - Lewisboro, NY

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,114.

From$749/night
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Pound Ridge Retreat: Private Trails, Fire Pit, Yoga + Fast Wi-Fi - Lewisboro, NY

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,228.

From$789/night
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Best Lewisboro, NY vacation rentals with a kitchen

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

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

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,756.

From$399/night
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Tranquil Country Contemporary - Lewisboro, NY

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,293.

From$571/night
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Private Country Getaway - Lewisboro, NY

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,158.

From$1,004/night
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Sophisticated Country Living - Lewisboro, NY

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $11,117.

From$1,249/night
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Our Favorite Family-Friendly Vacation Rentals in Lewisboro, NY

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

The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!. - Lewisboro, NY

The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!.

Guest House, Lewisboro

The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!. is a guest house in Lewisboro, with pet-friendly space, pool access, and kitchen access. This stay gives…

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About The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!.

The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!. is a guest house in Lewisboro, with pet-friendly space, 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, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,693.

From$185/night
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Seaside Serenity: 2B 1B, Patio,Near Beach - Lewisboro, NY

Seaside Serenity: 2B 1B, Patio,Near Beach

Cottage, Lewisboro

Seaside Serenity: 2B 1B, Patio,Near Beach is a cottage in Lewisboro, with pet-friendly space, easy beach access, and outdoor space. This stay gives travelers a comfortable base for…

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About Seaside Serenity: 2B 1B, Patio,Near Beach

Seaside Serenity: 2B 1B, Patio,Near Beach is a cottage in Lewisboro, with pet-friendly space, easy beach access, and outdoor 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 wifi, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,993.

From$271/night
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Cozy 1-bedroom lakefront cottage on beautiful Lake Mahopac. Come enjoy! - Lewisboro, NY

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,821.

From$315/night
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Newly Renovated Charming Greenwich Guest Cottage - Lewisboro, NY

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,962.

From$650/night
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