Vacation rentals in Pine Plains, NY

56 available vacation rental offers

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Best vacation rentals and Airbnb offers in Pine Plains, NY

MABEL: Michelle and Basquali's Enchanted Loveshack - Pine Plains, NY

MABEL: Michelle and Basquali's Enchanted Loveshack

Holiday Home, Pine Plains

MABEL: Michelle and Basquali's Enchanted Loveshack is a holiday home in Pine Plains, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the…

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About MABEL: Michelle and Basquali's Enchanted Loveshack

MABEL: Michelle and Basquali's Enchanted Loveshack is a holiday home in Pine Plains, 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: pool, pet friendly, pets friendly, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $907.

From$130/night
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Charming studio w/WiFi & AC in welcoming Amenia w/seasonal heated pool - Pine Plains, NY

Charming studio w/WiFi & AC in welcoming Amenia w/seasonal heated pool

Apartment, Pine Plains

Charming studio w/WiFi & AC in welcoming Amenia w/seasonal heated pool is a apartment in Pine Plains, with pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Charming studio w/WiFi & AC in welcoming Amenia w/seasonal heated pool

Charming studio w/WiFi & AC in welcoming Amenia w/seasonal heated pool is a apartment in Pine Plains, 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,369.

From$196/night
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the suite @ barn & bike - private, bucolic, serene setting - Pine Plains, NY

the suite @ barn & bike - private, bucolic, serene setting

Country House, Pine Plains

the suite @ barn & bike - private, bucolic, serene setting is a country house in Pine Plains, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About the suite @ barn & bike - private, bucolic, serene setting

the suite @ barn & bike - private, bucolic, serene setting is a country house in Pine Plains, 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 $1,601.

From$229/night
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Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats' - Pine Plains, NY

Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'

Cabin, Pine Plains

Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats' is a cabin in Pine Plains, with pet-friendly space, kitchen access, and a quieter setting. This stay gives…

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About Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'

Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats' is a cabin in Pine Plains, 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 $1,770.

From$253/night
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Vacation rentals with a pool in Pine Plains, NY

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

75 Acre Summer Retreat with Private Swimming Pond, Trails, and Cedar Hot Tub - Pine Plains, NY

75 Acre Summer Retreat with Private Swimming Pond, Trails, and Cedar Hot Tub

Holiday Home, Pine Plains

75 Acre Summer Retreat with Private Swimming Pond, Trails, and Cedar Hot Tub is a holiday home in Pine Plains, with pool access, kitchen access, and a quieter setting. This stay gives…

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About 75 Acre Summer Retreat with Private Swimming Pond, Trails, and Cedar Hot Tub

75 Acre Summer Retreat with Private Swimming Pond, Trails, and Cedar Hot Tub is a holiday home in Pine Plains, 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, kitchen, with kitchen, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,021.

From$289/night
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The Carriage House -2-bedroom house w/ Seasonal Heated Pool, WiFi, AC in Amenia - Pine Plains, NY

The Carriage House -2-bedroom house w/ Seasonal Heated Pool, WiFi, AC in Amenia

Holiday Home, Pine Plains

The Carriage House -2-bedroom house w/ Seasonal Heated Pool, WiFi, AC in Amenia is a holiday home in Pine Plains, with pet-friendly space, pool access, and kitchen access. This stay gives…

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About The Carriage House -2-bedroom house w/ Seasonal Heated Pool, WiFi, AC in Amenia

The Carriage House -2-bedroom house w/ Seasonal Heated Pool, WiFi, AC in Amenia is a holiday home in Pine Plains, 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 $2,730.

From$390/night
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Private and Tranquil Country Retreat - Pine Plains, NY

Private and Tranquil Country Retreat

Holiday Home, Pine Plains

Private and Tranquil Country Retreat is a holiday home in Pine Plains, 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 Pine Plains, 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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Modern Retreat - Private Pool & Lake Access - Pine Plains, NY

Modern Retreat - Private Pool & Lake Access

Holiday Home, Pine Plains

Modern Retreat - Private Pool & Lake Access is a holiday home in Pine Plains, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About Modern Retreat - Private Pool & Lake Access

Modern Retreat - Private Pool & Lake Access is a holiday home in Pine Plains, 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: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,595.

From$799/night
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Vacation rentals with parking in Pine Plains, NY

Find vacation rentals that make arriving by car easier.

Cozy Guest Suite At The Blue Ranch - Pine Plains, NY

Cozy Guest Suite At The Blue Ranch

Apartment, Pine Plains

Cozy Guest Suite At The Blue Ranch is a apartment in Pine Plains, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Cozy Guest Suite At The Blue Ranch

Cozy Guest Suite At The Blue Ranch is a apartment in Pine Plains, 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 $1,609.

From$230/night
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The Harlow House - Pine Plains, NY

The Harlow House

Guest House, Pine Plains

The Harlow House is a guest house in Pine Plains, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family…

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About The Harlow House

The Harlow House is a guest house in Pine Plains, 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 wifi, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,117.

From$267/night
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Copake Lake home near cultural attractions Of The Berkshires - Pine Plains, NY

Copake Lake home near cultural attractions Of The Berkshires

Holiday Home, Pine Plains

Copake Lake home near cultural attractions Of The Berkshires is a holiday home in Pine Plains, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Copake Lake home near cultural attractions Of The Berkshires

Copake Lake home near cultural attractions Of The Berkshires is a holiday home in Pine Plains, 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 $2,138.

From$305/night
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Nature Lover’s Mountaintop Retreat, 60 mile view...Privacy and tranquility - Pine Plains, NY

Nature Lover’s Mountaintop Retreat, 60 mile view...Privacy and tranquility

Guest House, Pine Plains

Nature Lover’s Mountaintop Retreat, 60 mile view...Privacy and tranquility is a guest house in Pine Plains, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About Nature Lover’s Mountaintop Retreat, 60 mile view...Privacy and tranquility

Nature Lover’s Mountaintop Retreat, 60 mile view...Privacy and tranquility is a guest house in Pine Plains, 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: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,585.

From$369/night
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Pet-friendly vacation rentals in Pine Plains, NY

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

Charming Columbia County Farm House - Pine Plains, NY

Charming Columbia County Farm House

Holiday Home, Pine Plains

Charming Columbia County Farm House is a holiday home in Pine Plains, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Charming Columbia County Farm House

Charming Columbia County Farm House is a holiday home in Pine Plains, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,726.

From$247/night
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Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County - Pine Plains, NY

Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County

Holiday Home, Pine Plains

Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County is a holiday home in Pine Plains, with pet-friendly space. This stay gives travelers a comfortable base for…

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About Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County

Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County is a holiday home in Pine Plains, 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, dryer, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,036.

From$291/night
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Luxurious & Modern 3 BR 1.5 Bath Log Cabin - Pine Plains, NY

Luxurious & Modern 3 BR 1.5 Bath Log Cabin

Cabin, Pine Plains

Luxurious & Modern 3 BR 1.5 Bath Log Cabin is a cabin in Pine Plains, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Luxurious & Modern 3 BR 1.5 Bath Log Cabin

Luxurious & Modern 3 BR 1.5 Bath Log Cabin is a cabin in Pine Plains, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,224.

From$318/night
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NEW: Chic Modern Barn Style Home in Fun Area - Pine Plains, NY

NEW: Chic Modern Barn Style Home in Fun Area

Holiday Home, Pine Plains

NEW: Chic Modern Barn Style Home in Fun Area is a holiday home in Pine Plains, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area is a holiday home in Pine Plains, 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 $4,640.

From$663/night
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Vacation rentals with a kitchen in Pine Plains, NY

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

Fall/Winter Mountain Spa Nature Retreat with 15 Acre Trail System - Pine Plains, NY

Fall/Winter Mountain Spa Nature Retreat with 15 Acre Trail System

Apartment, Pine Plains

Fall/Winter Mountain Spa Nature Retreat with 15 Acre Trail System is a apartment in Pine Plains, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for…

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About Fall/Winter Mountain Spa Nature Retreat with 15 Acre Trail System

Fall/Winter Mountain Spa Nature Retreat with 15 Acre Trail System is a apartment in Pine Plains, 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 $2,244.

From$321/night
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Cozy, spacious, New England Farmhouse close to Hotchkiss School & Lime Rock - Pine Plains, NY

Cozy, spacious, New England Farmhouse close to Hotchkiss School & Lime Rock

Holiday Home, Pine Plains

Cozy, spacious, New England Farmhouse close to Hotchkiss School & Lime Rock is a holiday home in Pine Plains, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Cozy, spacious, New England Farmhouse close to Hotchkiss School & Lime Rock

Cozy, spacious, New England Farmhouse close to Hotchkiss School & Lime Rock is a holiday home in Pine Plains, 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 $2,477.

From$354/night
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Perfect Hudson Valley Getaway with HOT TUB! - Pine Plains, NY

Perfect Hudson Valley Getaway with HOT TUB!

Holiday Home, Pine Plains

Perfect Hudson Valley Getaway with HOT TUB! is a holiday home in Pine Plains, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Perfect Hudson Valley Getaway with HOT TUB!

Perfect Hudson Valley Getaway with HOT TUB! is a holiday home in Pine Plains, 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,730.

From$390/night
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Copake Lakes Hidden Treasure - Pine Plains, NY

Copake Lakes Hidden Treasure

Holiday Home, Pine Plains

Copake Lakes Hidden Treasure is a holiday home in Pine Plains, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Copake Lakes Hidden Treasure

Copake Lakes Hidden Treasure is a holiday home in Pine Plains, 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 $2,860.

From$409/night
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Family-friendly vacation rentals in Pine Plains, NY

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

Beautiful Getaway - Right on the Lake-Close to Skiing - Pine Plains, NY

Beautiful Getaway - Right on the Lake-Close to Skiing

Holiday Home, Pine Plains

Beautiful Getaway - Right on the Lake-Close to Skiing is a holiday home in Pine Plains, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Beautiful Getaway - Right on the Lake-Close to Skiing

Beautiful Getaway - Right on the Lake-Close to Skiing is a holiday home in Pine Plains, with 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: kitchen, with kitchen, kids friendly, kids friendly videos or books, and beachfront.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,029.

From$290/night
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Stylish 3 Bedroom Cottage located in a Picturesque Lake community - Pine Plains, NY

Stylish 3 Bedroom Cottage located in a Picturesque Lake community

Cottage, Pine Plains

Stylish 3 Bedroom Cottage located in a Picturesque Lake community is a cottage in Pine Plains, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About Stylish 3 Bedroom Cottage located in a Picturesque Lake community

Stylish 3 Bedroom Cottage located in a Picturesque Lake community is a cottage in Pine Plains, 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 fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,265.

From$466/night
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Dog-friendly Copake Home w/ Sauna! - Pine Plains, NY

Dog-friendly Copake Home w/ Sauna!

Cottage, Pine Plains

Dog-friendly Copake Home w/ Sauna! is a cottage in Pine Plains, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Dog-friendly Copake Home w/ Sauna!

Dog-friendly Copake Home w/ Sauna! is a cottage in Pine Plains, 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 $4,956.

From$555/night
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Historic Barn Retreat w/ Pool & Pond Views Longview Pond Lodge by Avantstay - Pine Plains, NY

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

Cottage, Pine Plains

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

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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 Pine Plains, 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 $7,255.

From$817/night
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