Vacation rentals in Montgomery, NY

69 available vacation rental offers

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Best vacation rentals and Airbnb offers in Montgomery, NY

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail - Montgomery, NY

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

Holiday Home, Montgomery

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail is a holiday home in Montgomery, with pet-friendly space, pool access, and parking. This stay gives…

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About A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail is a holiday home in Montgomery, 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 $665.

From$95/night
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Cozy studio with WiFi and AC in charming New Windsor - Montgomery, NY

Cozy studio with WiFi and AC in charming New Windsor

Apartment, Montgomery

Cozy studio with WiFi and AC in charming New Windsor is a apartment in Montgomery, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy studio with WiFi and AC in charming New Windsor

Cozy studio with WiFi and AC in charming New Windsor is a apartment in Montgomery, with 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, parking, free parking, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $794.

From$113/night
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Buck's Homestead B&B - Montgomery, NY

Buck's Homestead B&B

B & B, Montgomery

Buck's Homestead B&B is a b & b in Montgomery, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Buck's Homestead B&B

Buck's Homestead B&B is a b & b in Montgomery, with 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 breakfast, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,584.

From$200/night
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The Borland House Inn - Montgomery, NY

The Borland House Inn

B & B, Montgomery

The Borland House Inn is a b & b in Montgomery, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About The Borland House Inn

The Borland House Inn is a b & b in Montgomery, 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 wifi, pet friendly, pets friendly, for couples, and wine or champagne.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,760.

From$211/night
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Vacation rentals with a pool in Montgomery, NY

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

Charming studio with Amazing hot tub a swimming pool,pool table. - Montgomery, NY

Charming studio with Amazing hot tub a swimming pool,pool table.

Apartment, Montgomery

Charming studio with Amazing hot tub a swimming pool,pool table. is a apartment in Montgomery, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About Charming studio with Amazing hot tub a swimming pool,pool table.

Charming studio with Amazing hot tub a swimming pool,pool table. is a apartment in Montgomery, 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,230.

From$176/night
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The 5-Star Peaceful Pool Retreat Only 5 mins from Legoland - Montgomery, NY

The 5-Star Peaceful Pool Retreat Only 5 mins from Legoland

Apartment, Montgomery

The 5-Star Peaceful Pool Retreat Only 5 mins from Legoland is a apartment in Montgomery, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable…

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About The 5-Star Peaceful Pool Retreat Only 5 mins from Legoland

The 5-Star Peaceful Pool Retreat Only 5 mins from Legoland is a apartment in Montgomery, with pool access, 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,573.

From$225/night
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HIKE, SWIM, STARGAZE IN FOREST BY THE MINNEWASKA STATE PARK SHAWANGUNK MOUNTAINS - Montgomery, NY

HIKE, SWIM, STARGAZE IN FOREST BY THE MINNEWASKA STATE PARK SHAWANGUNK MOUNTAINS

Cottage, Montgomery

HIKE, SWIM, STARGAZE IN FOREST BY THE MINNEWASKA STATE PARK SHAWANGUNK MOUNTAINS is a cottage in Montgomery, with pet-friendly space and pool access. This stay gives travelers a comfortable…

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About HIKE, SWIM, STARGAZE IN FOREST BY THE MINNEWASKA STATE PARK SHAWANGUNK MOUNTAINS

HIKE, SWIM, STARGAZE IN FOREST BY THE MINNEWASKA STATE PARK SHAWANGUNK MOUNTAINS is a cottage in Montgomery, with pet-friendly space and 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, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,759.

From$394/night
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Relax & Reconnect. Historic Farmhouse with Pool Near Mohonk & New Paltz - Montgomery, NY

Relax & Reconnect. Historic Farmhouse with Pool Near Mohonk & New Paltz

Holiday Home, Montgomery

Relax & Reconnect. Historic Farmhouse with Pool Near Mohonk & New Paltz is a holiday home in Montgomery, with pool access, kitchen access, and a quieter setting. This stay gives travelers a…

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About Relax & Reconnect. Historic Farmhouse with Pool Near Mohonk & New Paltz

Relax & Reconnect. Historic Farmhouse with Pool Near Mohonk & New Paltz is a holiday home in Montgomery, with pool access, 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,977.

From$425/night
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Vacation rentals with parking in Montgomery, NY

Find vacation rentals that make arriving by car easier.

Hudson River Retreat - Montgomery, NY

Hudson River Retreat

Apartment, Montgomery

Hudson River Retreat is a apartment in Montgomery, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Hudson River Retreat

Hudson River Retreat is a apartment in Montgomery, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,340.

From$191/night
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Shawangunk Getaway - brand new cozy 1-bedroom apartment in charming Wallkill. - Montgomery, NY

Shawangunk Getaway - brand new cozy 1-bedroom apartment in charming Wallkill.

Apartment, Montgomery

Shawangunk Getaway - brand new cozy 1-bedroom apartment in charming Wallkill. is a apartment in Montgomery, with parking and room for a group. This stay gives travelers a comfortable base…

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About Shawangunk Getaway - brand new cozy 1-bedroom apartment in charming Wallkill.

Shawangunk Getaway - brand new cozy 1-bedroom apartment in charming Wallkill. is a apartment in Montgomery, with 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: free cancellation, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,811.

From$259/night
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Cozy Lakeside Retreat - Montgomery, NY

Cozy Lakeside Retreat

Holiday Home, Montgomery

Cozy Lakeside Retreat is a holiday home in Montgomery, with pet-friendly space, parking, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cozy Lakeside Retreat

Cozy Lakeside Retreat is a holiday home in Montgomery, with pet-friendly space, parking, 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,500.

From$357/night
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Columbus Hotel - Montgomery, NY

Columbus Hotel

B & B, Montgomery

Columbus Hotel is a b & b in Montgomery, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Columbus Hotel

Columbus Hotel is a b & b in Montgomery, 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 $1,260.

From$150/night
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Pet-friendly vacation rentals in Montgomery, NY

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

Beautiful 1-bedroom apartment overlooking a pond on a 10 acre farm. - Montgomery, NY

Beautiful 1-bedroom apartment overlooking a pond on a 10 acre farm.

Holiday Home, Montgomery

Beautiful 1-bedroom apartment overlooking a pond on a 10 acre farm. is a holiday home in Montgomery, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Beautiful 1-bedroom apartment overlooking a pond on a 10 acre farm.

Beautiful 1-bedroom apartment overlooking a pond on a 10 acre farm. is a holiday home in Montgomery, 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 $1,233.

From$176/night
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Modern Home in Gardiner NY - Hudson Valley - Montgomery, NY

Modern Home in Gardiner NY - Hudson Valley

Apartment, Montgomery

Modern Home in Gardiner NY - Hudson Valley is a apartment in Montgomery, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Modern Home in Gardiner NY - Hudson Valley

Modern Home in Gardiner NY - Hudson Valley is a apartment in Montgomery, 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 $1,236.

From$177/night
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Woodsie - best glamping experience Middletown ny - Montgomery, NY

Woodsie - best glamping experience Middletown ny

Holiday Home, Montgomery

Woodsie - best glamping experience Middletown ny is a holiday home in Montgomery, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Woodsie - best glamping experience Middletown ny

Woodsie - best glamping experience Middletown ny is a holiday home in Montgomery, 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, pet friendly, pets friendly, tv, and bbq facilities.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,402.

From$200/night
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Pool house on a park-like estate, Pet friendly, 7 min to LegoLand. - Montgomery, NY

Pool house on a park-like estate, Pet friendly, 7 min to LegoLand.

Holiday Home, Montgomery

Pool house on a park-like estate, Pet friendly, 7 min to LegoLand. is a holiday home in Montgomery, with pet-friendly space and pool access. This stay gives travelers a comfortable base for…

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About Pool house on a park-like estate, Pet friendly, 7 min to LegoLand.

Pool house on a park-like estate, Pet friendly, 7 min to LegoLand. is a holiday home in Montgomery, with pet-friendly space and 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, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,620.

From$231/night
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Vacation rentals with a kitchen in Montgomery, NY

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

Spacious Suite (1 hr to Manhattan) - Montgomery, NY

Spacious Suite (1 hr to Manhattan)

Holiday Home, Montgomery

Spacious Suite (1 hr to Manhattan) is a holiday home in Montgomery, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Spacious Suite (1 hr to Manhattan)

Spacious Suite (1 hr to Manhattan) is a holiday home in Montgomery, 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 $1,393.

From$199/night
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3-bedroom new house b/w New Paltz and Newburgh. Quiet wooded area - Montgomery, NY

3-bedroom new house b/w New Paltz and Newburgh. Quiet wooded area

Holiday Home, Montgomery

3-bedroom new house b/w New Paltz and Newburgh. Quiet wooded area is a holiday home in Montgomery, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About 3-bedroom new house b/w New Paltz and Newburgh. Quiet wooded area

3-bedroom new house b/w New Paltz and Newburgh. Quiet wooded area is a holiday home in Montgomery, 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 $1,848.

From$264/night
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New for 2025 smart/whisper silent Heat and AC HVAC System. Temperature Control. - Montgomery, NY

New for 2025 smart/whisper silent Heat and AC HVAC System. Temperature Control.

Holiday Home, Montgomery

New for 2025 smart/whisper silent Heat and AC HVAC System. Temperature Control. is a holiday home in Montgomery, with pet-friendly space and kitchen access. This stay gives travelers a…

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About New for 2025 smart/whisper silent Heat and AC HVAC System. Temperature Control.

New for 2025 smart/whisper silent Heat and AC HVAC System. Temperature Control. is a holiday home in Montgomery, 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 $2,085.

From$298/night
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Pond Paradise: Marvelous 4-bedroom house with AC in charming Campbell Hall - Montgomery, NY

Pond Paradise: Marvelous 4-bedroom house with AC in charming Campbell Hall

Holiday Home, Montgomery

Pond Paradise: Marvelous 4-bedroom house with AC in charming Campbell Hall is a holiday home in Montgomery, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Pond Paradise: Marvelous 4-bedroom house with AC in charming Campbell Hall

Pond Paradise: Marvelous 4-bedroom house with AC in charming Campbell Hall is a holiday home in Montgomery, 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 $2,619.

From$374/night
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Family-friendly vacation rentals in Montgomery, NY

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

Cottage Suites - Montgomery, NY

Cottage Suites

Apartment, Montgomery

Cottage Suites is a apartment in Montgomery, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Cottage Suites

Cottage Suites is a apartment in Montgomery, 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 $1,169.

From$138/night
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Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro - Montgomery, NY

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Cottage, Montgomery

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro is a cottage in Montgomery, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro is a cottage in Montgomery, 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 $1,068.

From$153/night
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Cozy Cottage Getaway in Clintondale Near New Paltz - Montgomery, NY

Cozy Cottage Getaway in Clintondale Near New Paltz

Holiday Home, Montgomery

Cozy Cottage Getaway in Clintondale Near New Paltz is a holiday home in Montgomery, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy Cottage Getaway in Clintondale Near New Paltz

Cozy Cottage Getaway in Clintondale Near New Paltz is a holiday home in Montgomery, 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 $1,085.

From$155/night
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Cozy Haven: A Romantic Retreat in our Tiny House! - Montgomery, NY

Cozy Haven: A Romantic Retreat in our Tiny House!

Cottage, Montgomery

Cozy Haven: A Romantic Retreat in our Tiny House! is a cottage in Montgomery, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy Haven: A Romantic Retreat in our Tiny House!

Cozy Haven: A Romantic Retreat in our Tiny House! is a cottage in Montgomery, with 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, hot tub, kitchen, with kitchen, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,106.

From$158/night
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