Vacation rentals in Pleasant Valley, NY

50 available vacation rental offers

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Best vacation rentals and Airbnb offers in Pleasant Valley, NY

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

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

Holiday Home, Pleasant Valley

Beautiful 1-bedroom apartment overlooking a pond on a 10 acre farm. is a holiday home in Pleasant Valley, 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 Pleasant Valley, 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 $1,161.

From$166/night
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Tranquil 1-bedroom apartment with AC in charming Poughkeepsie - Pleasant Valley, NY

Tranquil 1-bedroom apartment with AC in charming Poughkeepsie

Apartment, Pleasant Valley

Tranquil 1-bedroom apartment with AC in charming Poughkeepsie is a apartment in Pleasant Valley, with room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Tranquil 1-bedroom apartment with AC in charming Poughkeepsie

Tranquil 1-bedroom apartment with AC in charming Poughkeepsie is a apartment in Pleasant Valley, 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, washer, ac, air conditioning, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,608.

From$230/night
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Romantic Log Cabin on Privately-Owned Lake with Fireplace - Pleasant Valley, NY

Romantic Log Cabin on Privately-Owned Lake with Fireplace

Cabin, Pleasant Valley

Romantic Log Cabin on Privately-Owned Lake with Fireplace is a cabin in Pleasant Valley, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Romantic Log Cabin on Privately-Owned Lake with Fireplace

Romantic Log Cabin on Privately-Owned Lake with Fireplace is a cabin in Pleasant Valley, 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 $1,865.

From$266/night
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1850s Barn Studio on 4.5 Hudson Valley Acres! - Pleasant Valley, NY

1850s Barn Studio on 4.5 Hudson Valley Acres!

Apartment, Pleasant Valley

1850s Barn Studio on 4.5 Hudson Valley Acres! is a apartment in Pleasant Valley, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 1850s Barn Studio on 4.5 Hudson Valley Acres!

1850s Barn Studio on 4.5 Hudson Valley Acres! is a apartment in Pleasant Valley, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,004.

From$286/night
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Vacation rentals with a pool in Pleasant Valley, NY

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

Private and Tranquil Country Retreat - Pleasant Valley, NY

Private and Tranquil Country Retreat

Holiday Home, Pleasant Valley

Private and Tranquil Country Retreat is a holiday home in Pleasant Valley, with pet-friendly space, pool access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Private and Tranquil Country Retreat

Private and Tranquil Country Retreat is a holiday home in Pleasant Valley, with pet-friendly space, pool 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, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,954.

From$565/night
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Enjoy pool time at our spacious home; minutes from the village of Millbrook! - Pleasant Valley, NY

Enjoy pool time at our spacious home; minutes from the village of Millbrook!

Holiday Home, Pleasant Valley

Enjoy pool time at our spacious home; minutes from the village of Millbrook! is a holiday home in Pleasant Valley, with pet-friendly space, pool access, and kitchen access. This stay gives…

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About Enjoy pool time at our spacious home; minutes from the village of Millbrook!

Enjoy pool time at our spacious home; minutes from the village of Millbrook! is a holiday home in Pleasant Valley, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,749.

From$678/night
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Historic Barn Retreat w/ Pool & Pond Views | Longview Pond Lodge by AvantStay - Pleasant Valley, NY

Historic Barn Retreat w/ Pool & Pond Views | Longview Pond Lodge by AvantStay

Holiday Home, Pleasant Valley

Historic Barn Retreat w/ Pool & Pond Views · Longview Pond Lodge by AvantStay is a holiday home in Pleasant Valley, with pool access, kitchen access, and a quieter setting. This stay gives…

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About Historic Barn Retreat w/ Pool & Pond Views | Longview Pond Lodge by AvantStay

Historic Barn Retreat w/ Pool & Pond Views · Longview Pond Lodge by AvantStay is a holiday home in Pleasant Valley, 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 $5,604.

From$801/night
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Historic Barn Retreat w/ Pool & Pond Views Longview Pond Lodge by Avantstay - Pleasant Valley, NY

Historic Barn Retreat w/ Pool & Pond Views Longview Pond Lodge by Avantstay

Cottage, Pleasant Valley

Historic Barn Retreat w/ Pool & Pond Views Longview Pond Lodge by Avantstay is a cottage in Pleasant Valley, with pool access and a quieter setting. This stay gives travelers a comfortable…

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About Historic Barn Retreat w/ Pool & Pond Views Longview Pond Lodge by Avantstay

Historic Barn Retreat w/ Pool & Pond Views Longview Pond Lodge by Avantstay is a cottage in Pleasant Valley, with pool 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,203.

From$811/night
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Vacation rentals with parking in Pleasant Valley, NY

Find vacation rentals that make arriving by car easier.

The Gables of Rhinebeck Inn - Pleasant Valley, NY

The Gables of Rhinebeck Inn

Guest House, Pleasant Valley

The Gables of Rhinebeck Inn is a guest house in Pleasant Valley, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About The Gables of Rhinebeck Inn

The Gables of Rhinebeck Inn is a guest house in Pleasant Valley, 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 wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,101.

From$363/night
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Staatsburg Parsonage - A tranquil 4-bedroom house with AC - Pleasant Valley, NY

Staatsburg Parsonage - A tranquil 4-bedroom house with AC

Holiday Home, Pleasant Valley

Staatsburg Parsonage - A tranquil 4-bedroom house with AC is a holiday home in Pleasant Valley, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Staatsburg Parsonage - A tranquil 4-bedroom house with AC

Staatsburg Parsonage - A tranquil 4-bedroom house with AC is a holiday home in Pleasant Valley, 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 $2,782.

From$397/night
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Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY - Pleasant Valley, NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Holiday Home, Pleasant Valley

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY is a holiday home in Pleasant Valley, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY is a holiday home in Pleasant Valley, 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 $3,531.

From$504/night
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Forest retreat& Gathering Space- NEW!!! - Pleasant Valley, NY

Forest retreat& Gathering Space- NEW!!!

Holiday Home, Pleasant Valley

Forest retreat& Gathering Space- NEW!!! is a holiday home in Pleasant Valley, with parking and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Forest retreat& Gathering Space- NEW!!!

Forest retreat& Gathering Space- NEW!!! is a holiday home in Pleasant Valley, with 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, parking, free parking, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,732.

From$533/night
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Pet-friendly vacation rentals in Pleasant Valley, NY

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

VACATION Mod Cottage, Idyllic Setting & Every Amenity - Pleasant Valley, NY

VACATION Mod Cottage, Idyllic Setting & Every Amenity

Cottage, Pleasant Valley

VACATION Mod Cottage, Idyllic Setting & Every Amenity is a cottage in Pleasant Valley, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About VACATION Mod Cottage, Idyllic Setting & Every Amenity

VACATION Mod Cottage, Idyllic Setting & Every Amenity is a cottage in Pleasant Valley, 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 $2,298.

From$328/night
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for the creative spirit, swimming dock on pond, horses to pet, Fire pit - Pleasant Valley, NY

for the creative spirit, swimming dock on pond, horses to pet, Fire pit

Holiday Home, Pleasant Valley

for the creative spirit, swimming dock on pond, horses to pet, Fire pit is a holiday home in Pleasant Valley, with pet-friendly space, pool access, and kitchen access. This stay gives…

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About for the creative spirit, swimming dock on pond, horses to pet, Fire pit

for the creative spirit, swimming dock on pond, horses to pet, Fire pit is a holiday home in Pleasant Valley, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,373.

From$339/night
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Fire Pit + On-Site Pond: Hudson Valley Home! - Pleasant Valley, NY

Fire Pit + On-Site Pond: Hudson Valley Home!

Holiday Home, Pleasant Valley

Fire Pit + On-Site Pond: Hudson Valley Home! is a holiday home in Pleasant Valley, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Fire Pit + On-Site Pond: Hudson Valley Home!

Fire Pit + On-Site Pond: Hudson Valley Home! is a holiday home in Pleasant Valley, 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 $2,576.

From$368/night
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Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway - Pleasant Valley, NY

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Holiday Home, Pleasant Valley

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway is a holiday home in Pleasant Valley, with pet-friendly space, kitchen access, and room for a group. This stay gives…

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About Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway is a holiday home in Pleasant Valley, 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 $3,361.

From$480/night
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Vacation rentals with a kitchen in Pleasant Valley, NY

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

Charming former church near the Hudson w/ hot tub. A tranquil retreat. - Pleasant Valley, NY

Charming former church near the Hudson w/ hot tub. A tranquil retreat.

Holiday Home, Pleasant Valley

Charming former church near the Hudson w/ hot tub. A tranquil retreat. is a holiday home in Pleasant Valley, with kitchen access and a quieter setting. This stay gives travelers a…

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About Charming former church near the Hudson w/ hot tub. A tranquil retreat.

Charming former church near the Hudson w/ hot tub. A tranquil retreat. is a holiday home in Pleasant Valley, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,509.

From$358/night
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Artist's Retreat: Farm Stay with Gas Fireplace, Sauna, and Saltwater Hot Tub - Pleasant Valley, NY

Artist's Retreat: Farm Stay with Gas Fireplace, Sauna, and Saltwater Hot Tub

Holiday Home, Pleasant Valley

Artist's Retreat: Farm Stay with Gas Fireplace, Sauna, and Saltwater Hot Tub is a holiday home in Pleasant Valley, with pet-friendly space, kitchen access, and a quieter setting. This stay…

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About Artist's Retreat: Farm Stay with Gas Fireplace, Sauna, and Saltwater Hot Tub

Artist's Retreat: Farm Stay with Gas Fireplace, Sauna, and Saltwater Hot Tub is a holiday home in Pleasant Valley, 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, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,326.

From$475/night
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Incredible spacious family friendly getaway - Pleasant Valley, NY

Incredible spacious family friendly getaway

Holiday Home, Pleasant Valley

Incredible spacious family friendly getaway is a holiday home in Pleasant Valley, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Incredible spacious family friendly getaway

Incredible spacious family friendly getaway is a holiday home in Pleasant Valley, 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,763.

From$538/night
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Historic, Converted Mill w/Beautiful Waterfall & Stream, 2 hr drive from NYC - Pleasant Valley, NY

Historic, Converted Mill w/Beautiful Waterfall & Stream, 2 hr drive from NYC

Holiday Home, Pleasant Valley

Historic, Converted Mill w/Beautiful Waterfall & Stream, 2 hr drive from NYC is a holiday home in Pleasant Valley, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Historic, Converted Mill w/Beautiful Waterfall & Stream, 2 hr drive from NYC

Historic, Converted Mill w/Beautiful Waterfall & Stream, 2 hr drive from NYC is a holiday home in Pleasant Valley, 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 $6,027.

From$861/night
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Family-friendly vacation rentals in Pleasant Valley, NY

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

Scenic Hudson Valley Getaway • Farms & Vineyards - Pleasant Valley, NY

Scenic Hudson Valley Getaway • Farms & Vineyards

Cottage, Pleasant Valley

Scenic Hudson Valley Getaway · Farms & Vineyards is a cottage in Pleasant Valley, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Scenic Hudson Valley Getaway • Farms & Vineyards

Scenic Hudson Valley Getaway · Farms & Vineyards is a cottage in Pleasant Valley, 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 $2,111.

From$302/night
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Charming Rhinebeck Cottage, 5 min. from town, King Bed! - Pleasant Valley, NY

Charming Rhinebeck Cottage, 5 min. from town, King Bed!

Cottage, Pleasant Valley

Charming Rhinebeck Cottage, 5 min. from town, King Bed! is a cottage in Pleasant Valley, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Charming Rhinebeck Cottage, 5 min. from town, King Bed!

Charming Rhinebeck Cottage, 5 min. from town, King Bed! is a cottage in Pleasant Valley, 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,238.

From$320/night
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West Park/Esopus Victorian - 2 King and 1 Queen Bed - Pleasant Valley, NY

West Park/Esopus Victorian - 2 King and 1 Queen Bed

Cottage, Pleasant Valley

West Park/Esopus Victorian - 2 King and 1 Queen Bed is a cottage in Pleasant Valley, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About West Park/Esopus Victorian - 2 King and 1 Queen Bed

West Park/Esopus Victorian - 2 King and 1 Queen Bed is a cottage in Pleasant Valley, 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 $2,424.

From$346/night
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Converted Barns, Estate Setting , & Pool in Hudson Valley near Millbrook - Pleasant Valley, NY

Converted Barns, Estate Setting , & Pool in Hudson Valley near Millbrook

Holiday Home, Pleasant Valley

Converted Barns, Estate Setting , & Pool in Hudson Valley near Millbrook is a holiday home in Pleasant Valley, with pool access and kitchen access. This stay gives travelers a comfortable…

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About Converted Barns, Estate Setting , & Pool in Hudson Valley near Millbrook

Converted Barns, Estate Setting , & Pool in Hudson Valley near Millbrook is a holiday home in Pleasant Valley, 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, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,705.

From$815/night
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