Vacation rentals in Shady, NY

200 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Shady, NY

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi! - Shady, NY

Groovy 1 Bedroom Apartment in Woodstock - AC & WiFi!

Apartment, Shady

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

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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 Shady, 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 $1,615.

From$167/night
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Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream - Shady, NY

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Cottage, Shady

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream is a cottage in Shady, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable…

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About Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream is a cottage in Shady, 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 $1,543.

From$168/night
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Mountain view, mid-century style, 1 mile to town! - Shady, NY

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

Cottage, Shady

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

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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 Shady, 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 $1,663.

From$176/night
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Beautiful Top Floor Unit in Downtown Woodstock! - Shady, NY

Beautiful Top Floor Unit in Downtown Woodstock!

Apartment, Shady

Beautiful Top Floor Unit in Downtown Woodstock! is a apartment in Shady. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Beautiful Top Floor Unit in Downtown Woodstock!

Beautiful Top Floor Unit in Downtown Woodstock! is a apartment in Shady. 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, ac, air conditioning, heating, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,812.

From$189/night
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Browse Vacation Rentals with a Pool in Shady, NY

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

Catskill Mountains Vacation Condo at Scribner Hollow with great mountain views - Shady, NY

Catskill Mountains Vacation Condo at Scribner Hollow with great mountain views

Condo, Shady

Catskill Mountains Vacation Condo at Scribner Hollow with great mountain views is a condo in Shady, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About Catskill Mountains Vacation Condo at Scribner Hollow with great mountain views

Catskill Mountains Vacation Condo at Scribner Hollow with great mountain views is a condo in Shady, 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, kitchen, with kitchen, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $995.

From$108/night
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Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Unwind! - Shady, NY

Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Unwind!

Apartment, Shady

Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Unwind! is a apartment in Shady, with pool access and kitchen access. This stay gives travelers a comfortable base…

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About Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Unwind!

Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Unwind! is a apartment in Shady, 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, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,463.

From$163/night
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Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch - Shady, NY

Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch

Cottage, Shady

Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch is a cottage in Shady, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch

Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch is a cottage in Shady, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,949.

From$320/night
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CATSKILLS SKIING : SO CLOSE TO Hunter, Wyndham, Belleayre area - Shady, NY

CATSKILLS SKIING : SO CLOSE TO Hunter, Wyndham, Belleayre area

Chalet, Shady

CATSKILLS SKIING : SO CLOSE TO Hunter, Wyndham, Belleayre area is a chalet in Shady, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About CATSKILLS SKIING : SO CLOSE TO Hunter, Wyndham, Belleayre area

CATSKILLS SKIING : SO CLOSE TO Hunter, Wyndham, Belleayre area is a chalet in Shady, 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, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,771.

From$174/night
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Best Shady, NY vacation rentals with parking

Find vacation rentals that make arriving by car easier.

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY - Shady, NY

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Cabin, Shady

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY is a cabin in Shady, with pet-friendly space and parking. This stay gives travelers a comfortable base for…

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About 'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY is a cabin in Shady, 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 $1,109.

From$128/night
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Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby - Shady, NY

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

Apartment, Shady

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

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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 Shady, 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 $1,325.

From$152/night
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Woodland Cozy Cabin Catskills - Shady, NY

Woodland Cozy Cabin Catskills

Cabin, Shady

Woodland Cozy Cabin Catskills is a cabin in Shady, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Woodland Cozy Cabin Catskills

Woodland Cozy Cabin Catskills is a cabin in Shady, 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 $1,773.

From$185/night
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Little red house just outside of Woodstock - Shady, NY

Little red house just outside of Woodstock

Cottage, Shady

Little red house just outside of Woodstock is a cottage in Shady, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Little red house just outside of Woodstock

Little red house just outside of Woodstock is a cottage in Shady, 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,577.

From$276/night
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Best Pet-Friendly Vacation Rentals in Shady, NY

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

Fully Furnished 1BR Apt – Ideal for Traveling Professionals - Shady, NY

Fully Furnished 1BR Apt – Ideal for Traveling Professionals

Apartment, Shady

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

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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 Shady, 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 $1,238.

From$135/night
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Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn - Shady, NY

Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn

Cottage, Shady

Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn is a cottage in Shady, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring the…

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About Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn

Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn is a cottage in Shady, with pet-friendly space, outdoor 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, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,178.

From$197/night
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Woodstock Paradise with Gardens / Private Heated Pool--& Cozy Winter Wonderland - Shady, NY

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

Holiday Home, Shady

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

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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 Shady, 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 $2,307.

From$252/night
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A pleasant space in a pleasant neighborhood in a beautiful part of the country! - Shady, NY

A pleasant space in a pleasant neighborhood in a beautiful part of the country!

Apartment, Shady

A pleasant space in a pleasant neighborhood in a beautiful part of the country! is a apartment in Shady, with pet-friendly space and kitchen access. This stay gives travelers a comfortable…

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About A pleasant space in a pleasant neighborhood in a beautiful part of the country!

A pleasant space in a pleasant neighborhood in a beautiful part of the country! is a apartment in Shady, 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 $2,442.

From$261/night
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Best Shady, NY vacation rentals with a kitchen

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

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna - Shady, NY

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Cabin, Shady

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna is a cabin in Shady, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna is a cabin in Shady, 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 $1,841.

From$201/night
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Cozy Cottage with Great Views Glenford New York - Shady, NY

Cozy Cottage with Great Views Glenford New York

Holiday Home, Shady

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

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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 Shady, 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 $2,243.

From$250/night
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HUGE KITCHEN 4 Private Acres, 7 Min to Town, AC, Fireplace - Opt. Studio addl. - Shady, NY

HUGE KITCHEN 4 Private Acres, 7 Min to Town, AC, Fireplace - Opt. Studio addl.

Holiday Home, Shady

HUGE KITCHEN 4 Private Acres, 7 Min to Town, AC, Fireplace - Opt. Studio addl. is a holiday home in Shady, with pet-friendly space and kitchen access. This stay gives travelers a…

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About HUGE KITCHEN 4 Private Acres, 7 Min to Town, AC, Fireplace - Opt. Studio addl.

HUGE KITCHEN 4 Private Acres, 7 Min to Town, AC, Fireplace - Opt. Studio addl. is a holiday home in Shady, 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 $2,460.

From$263/night
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Romantic Cottage -Amazing Views -Spa -Woodstock NY - Shady, NY

Romantic Cottage -Amazing Views -Spa -Woodstock NY

Holiday Home, Shady

Romantic Cottage -Amazing Views -Spa -Woodstock NY is a holiday home in Shady, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Romantic Cottage -Amazing Views -Spa -Woodstock NY

Romantic Cottage -Amazing Views -Spa -Woodstock NY is a holiday home in Shady, 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, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,499.

From$276/night
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Our Favorite Family-Friendly Vacation Rentals in Shady, NY

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

The Cabin at Chichester in the Catskills Mountains - Shady, NY

The Cabin at Chichester in the Catskills Mountains

Cottage, Shady

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

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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 Shady, 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 $1,273.

From$144/night
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Lovely cottage located on Plattekill Stream - Shady, NY

Lovely cottage located on Plattekill Stream

Cabin, Shady

Lovely cottage located on Plattekill Stream is a cabin in Shady, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Lovely cottage located on Plattekill Stream

Lovely cottage located on Plattekill Stream is a cabin in Shady, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,312.

From$145/night
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Lovely Cottage Getaway in the Mountains near Phoenicia, New York - Shady, NY

Lovely Cottage Getaway in the Mountains near Phoenicia, New York

Holiday Home, Shady

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

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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 Shady, 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 $1,400.

From$164/night
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Quaint Cottage w/ Peloton & Sauna near Hiking - Shady, NY

Quaint Cottage w/ Peloton & Sauna near Hiking

Holiday Home, Shady

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

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About Quaint Cottage w/ Peloton & Sauna near Hiking

Quaint Cottage w/ Peloton & Sauna near Hiking is a holiday home in Shady, 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 $1,702.

From$178/night
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