Vacation rentals in Town of Olive, NY

121 available vacation rental offers

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Best vacation rentals and Airbnb offers in Town of Olive, NY

Fully Furnished 1BR Apt – Ideal for Traveling Professionals - Town of Olive, NY

Fully Furnished 1BR Apt – Ideal for Traveling Professionals

Apartment, Town of Olive

Fully Furnished 1BR Apt – Ideal for Traveling Professionals is a apartment in Town of Olive, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for…

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About Fully Furnished 1BR Apt – Ideal for Traveling Professionals

Fully Furnished 1BR Apt – Ideal for Traveling Professionals is a apartment in Town of Olive, with pet-friendly space 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, heating, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,105.

From$158/night
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Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi! - Town of Olive, NY

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

Apartment, Town of Olive

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi! is a apartment in Town of Olive, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi! is a apartment in Town of Olive, 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 $1,242.

From$177/night
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Mountain view, mid-century style, 1 mile to town! - Town of Olive, NY

Mountain view, mid-century style, 1 mile to town!

Cottage, Town of Olive

Mountain view, mid-century style, 1 mile to town! is a cottage in Town of Olive, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Mountain view, mid-century style, 1 mile to town!

Mountain view, mid-century style, 1 mile to town! is a cottage in Town of Olive, 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 $1,484.

From$212/night
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Quaint Cottage w/ Peloton & Sauna near Hiking - Town of Olive, NY

Quaint Cottage w/ Peloton & Sauna near Hiking

Holiday Home, Town of Olive

Quaint Cottage w/ Peloton & Sauna near Hiking is a holiday home in Town of Olive, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Quaint Cottage w/ Peloton & Sauna near Hiking

Quaint Cottage w/ Peloton & Sauna near Hiking is a holiday home in Town of Olive, 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 $1,496.

From$214/night
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Vacation rentals with a pool in Town of Olive, NY

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

Cold Spring Lodge - Cabin 2 - Town of Olive, NY

Cold Spring Lodge - Cabin 2

Cabin, Town of Olive

Cold Spring Lodge - Cabin 2 is a cabin in Town of Olive, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cold Spring Lodge - Cabin 2

Cold Spring Lodge - Cabin 2 is a cabin in Town of Olive, 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 $1,293.

From$185/night
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Cold Spring Lodge - Cabin 4 - Town of Olive, NY

Cold Spring Lodge - Cabin 4

Cabin, Town of Olive

Cold Spring Lodge - Cabin 4 is a cabin in Town of Olive, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cold Spring Lodge - Cabin 4

Cold Spring Lodge - Cabin 4 is a cabin in Town of Olive, 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 $1,614.

From$231/night
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Woodstock Paradise with Gardens / Private Heated Pool--& Cozy Winter Wonderland - Town of Olive, NY

Woodstock Paradise with Gardens / Private Heated Pool--& Cozy Winter Wonderland

Holiday Home, Town of Olive

Woodstock Paradise with Gardens / Private Heated Pool--& Cozy Winter Wonderland is a holiday home in Town of Olive, with pet-friendly space and pool access. This stay gives travelers a…

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About Woodstock Paradise with Gardens / Private Heated Pool--& Cozy Winter Wonderland

Woodstock Paradise with Gardens / Private Heated Pool--& Cozy Winter Wonderland is a holiday home in Town of Olive, 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,059.

From$294/night
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Spring Special:Relax, Save, Farmhouse 2hrs NYC - Town of Olive, NY

Spring Special:Relax, Save, Farmhouse 2hrs NYC

Holiday Home, Town of Olive

Spring Special:Relax, Save, Farmhouse 2hrs NYC is a holiday home in Town of Olive, with pet-friendly space, pool access, and a quieter setting. This stay gives travelers a comfortable base…

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About Spring Special:Relax, Save, Farmhouse 2hrs NYC

Spring Special:Relax, Save, Farmhouse 2hrs NYC is a holiday home in Town of Olive, 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,848.

From$550/night
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Vacation rentals with parking in Town of Olive, NY

Find vacation rentals that make arriving by car easier.

Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby - Town of Olive, NY

Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby

Apartment, Town of Olive

Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby is a apartment in Town of Olive, with pet-friendly space and parking. This stay gives travelers a comfortable…

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About Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby

Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby is a apartment in Town of Olive, 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, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,183.

From$169/night
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Morning Glory B n B Woodstock NY - Town of Olive, NY

Morning Glory B n B Woodstock NY

B & B, Town of Olive

Morning Glory B n B Woodstock NY is a b & b in Town of Olive, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY is a b & b in Town of Olive, 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 breakfast, free wifi, parking, paid parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,664.

From$216/night
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Morning Glory B n B Woodstock NY - Town of Olive, NY

Morning Glory B n B Woodstock NY

B & B, Town of Olive

Morning Glory B n B Woodstock NY is a b & b in Town of Olive, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY is a b & b in Town of Olive, 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 breakfast, parking, free parking, internet, and non smoking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,695.

From$216/night
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Coldbrook Bed and Breakfast - Town of Olive, NY

Coldbrook Bed and Breakfast

B & B, Town of Olive

Coldbrook Bed and Breakfast is a b & b in Town of Olive, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Coldbrook Bed and Breakfast

Coldbrook Bed and Breakfast is a b & b in Town of Olive, 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 breakfast, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,468.

From$315/night
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Pet-friendly vacation rentals in Town of Olive, NY

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

Beautiful Barn on 7 Acres - Get Away from it All - Town of Olive, NY

Beautiful Barn on 7 Acres - Get Away from it All

Cabin, Town of Olive

Beautiful Barn on 7 Acres - Get Away from it All is a cabin in Town of Olive, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Beautiful Barn on 7 Acres - Get Away from it All

Beautiful Barn on 7 Acres - Get Away from it All is a cabin in Town of Olive, 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 $1,148.

From$164/night
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Catskills Hideaway w/ Sauna Minutes from Hiking - Town of Olive, NY

Catskills Hideaway w/ Sauna Minutes from Hiking

Guest House, Town of Olive

Catskills Hideaway w/ Sauna Minutes from Hiking is a guest house in Town of Olive, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Catskills Hideaway w/ Sauna Minutes from Hiking

Catskills Hideaway w/ Sauna Minutes from Hiking is a guest house in Town of Olive, 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 $1,701.

From$243/night
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A Romantic Escape, Woodstock Barn by A Stream with Hot Tub - Town of Olive, NY

A Romantic Escape, Woodstock Barn by A Stream with Hot Tub

Holiday Home, Town of Olive

A Romantic Escape, Woodstock Barn by A Stream with Hot Tub is a holiday home in Town of Olive, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About A Romantic Escape, Woodstock Barn by A Stream with Hot Tub

A Romantic Escape, Woodstock Barn by A Stream with Hot Tub is a holiday home in Town of Olive, 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: hot tub, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,120.

From$303/night
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Coldbrook Bed and Breakfast - Town of Olive, NY

Coldbrook Bed and Breakfast

B & B, Town of Olive

Coldbrook Bed and Breakfast is a b & b in Town of Olive, 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 Coldbrook Bed and Breakfast

Coldbrook Bed and Breakfast is a b & b in Town of Olive, 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 breakfast, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,550.

From$318/night
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Vacation rentals with a kitchen in Town of Olive, NY

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

Stone Ridge Stunner - Town of Olive, NY

Stone Ridge Stunner

Holiday Home, Town of Olive

Stone Ridge Stunner is a holiday home in Town of Olive, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Stone Ridge Stunner

Stone Ridge Stunner is a holiday home in Town of Olive, 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: kitchen, with kitchen, tv, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,508.

From$215/night
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NEW-Romantic Lake View Carriage House - Town of Olive, NY

NEW-Romantic Lake View Carriage House

Cabin, Town of Olive

NEW-Romantic Lake View Carriage House is a cabin in Town of Olive, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About NEW-Romantic Lake View Carriage House

NEW-Romantic Lake View Carriage House is a cabin in Town of Olive, 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 $1,689.

From$241/night
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Most Charming, Most quiet place in the Catskills--Willow-brook Cottage - Town of Olive, NY

Most Charming, Most quiet place in the Catskills--Willow-brook Cottage

Cabin, Town of Olive

Most Charming, Most quiet place in the Catskills--Willow-brook Cottage is a cabin in Town of Olive, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About Most Charming, Most quiet place in the Catskills--Willow-brook Cottage

Most Charming, Most quiet place in the Catskills--Willow-brook Cottage is a cabin in Town of Olive, 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, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,911.

From$273/night
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Modern Nature Escape w/Barrel Sauna & Yurt - Town of Olive, NY

Modern Nature Escape w/Barrel Sauna & Yurt

Guest House, Town of Olive

Modern Nature Escape w/Barrel Sauna & Yurt is a guest house in Town of Olive, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Modern Nature Escape w/Barrel Sauna & Yurt

Modern Nature Escape w/Barrel Sauna & Yurt is a guest house in Town of Olive, 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 $3,053.

From$436/night
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Family-friendly vacation rentals in Town of Olive, NY

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

The Cabin at Chichester in the Catskills Mountains - Town of Olive, NY

The Cabin at Chichester in the Catskills Mountains

Cottage, Town of Olive

The Cabin at Chichester in the Catskills Mountains is a cottage in Town of Olive, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About The Cabin at Chichester in the Catskills Mountains

The Cabin at Chichester in the Catskills Mountains is a cottage in Town of Olive, 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 $1,137.

From$162/night
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Lovely Cottage Getaway in the Mountains near Phoenicia, New York - Town of Olive, NY

Lovely Cottage Getaway in the Mountains near Phoenicia, New York

Holiday Home, Town of Olive

Lovely Cottage Getaway in the Mountains near Phoenicia, New York is a holiday home in Town of Olive, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base…

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About Lovely Cottage Getaway in the Mountains near Phoenicia, New York

Lovely Cottage Getaway in the Mountains near Phoenicia, New York is a holiday home in Town of Olive, 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: hot tub, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,302.

From$186/night
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The Hideout Catskills Cottage - Town of Olive, NY

The Hideout Catskills Cottage

Holiday Home, Town of Olive

The Hideout Catskills Cottage is a holiday home in Town of Olive, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About The Hideout Catskills Cottage

The Hideout Catskills Cottage is a holiday home in Town of Olive, 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 accessible.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,199.

From$247/night
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Cozy Cottage with Great Views Glenford New York - Town of Olive, NY

Cozy Cottage with Great Views Glenford New York

Holiday Home, Town of Olive

Cozy Cottage with Great Views Glenford New York is a holiday home in Town of Olive, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Cozy Cottage with Great Views Glenford New York

Cozy Cottage with Great Views Glenford New York is a holiday home in Town of Olive, 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 $2,003.

From$286/night
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