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Preston Hollow Holiday Rentals

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50 rentals in Preston Hollow.
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Great 5 BR House !!!!, holiday rental in Preston Hollow

Great 5 BR House !!!!

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Tentrr Signature Site - Creekside Zen in Catskills, holiday rental in Preston Hollow

Tentrr Signature Site - Creekside Zen in Catskills

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub, holiday rental in Preston Hollow

Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dancing Horse Farm - Ski Lodge and Farm 3 Miles from Windham Mountain, holiday rental in Preston Hollow

Dancing Horse Farm - Ski Lodge and Farm 3 Miles from Windham Mountain

9 bedrooms
5 bathrooms
Sleeps 30
Match: Sleeps
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*4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw, holiday rental in Preston Hollow

*4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Windham Family Getaway (Brand New!), holiday rental in Preston Hollow

Windham Family Getaway (Brand New!)

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Relax!! Escape the city!! Updated condo w Mtn views from deck w/ turbo internet, holiday rental in Preston Hollow

Relax!! Escape the city!! Updated condo w Mtn views from deck w/ turbo internet

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The perfect mountain getaway nestled in the woods 2 min from downtown Windham., holiday rental in Preston Hollow

The perfect mountain getaway nestled in the woods 2 min from downtown Windham.

4 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Spacious Retreat with Luxurious View, holiday rental in Preston Hollow

Spacious Retreat with Luxurious View

5 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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'New Home' Idyllic  Mt Views ,Pond & Horse farm views 2 min to Town, holiday rental in Preston Hollow

'New Home' Idyllic Mt Views ,Pond & Horse farm views 2 min to Town

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Year-Round Relaxing Mountain Escape, holiday rental in Preston Hollow

Year-Round Relaxing Mountain Escape

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Cozy Log Cabin, holiday rental in Preston Hollow

Cozy Log Cabin

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Mountain House Retreat, holiday rental in Preston Hollow

Mountain House Retreat

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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FAB FUN GREEN BUILT FARMHOUSE ON 17 ACRES, holiday rental in Preston Hollow

FAB FUN GREEN BUILT FARMHOUSE ON 17 ACRES

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Charming Water Front Log Home, holiday rental in Preston Hollow

Secluded Charming Water Front Log Home

4 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***, holiday rental in Preston Hollow

***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Spacious Mountain Escape - Minutes to Windham/Hunter, holiday rental in Preston Hollow

Spacious Mountain Escape - Minutes to Windham/Hunter

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Windham Skiers Book Now! Cottage North Catskills, holiday rental in Preston Hollow

Windham Skiers Book Now! Cottage North Catskills

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Historic Catskill Mountain House close to Windham, holiday rental in Preston Hollow

Historic Catskill Mountain House close to Windham

7 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Windham Mountain Ski House with Great Views, holiday rental in Preston Hollow

Windham Mountain Ski House with Great Views

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Mountain House: The Perfect 4 Season Retreat, holiday rental in Preston Hollow

The Mountain House: The Perfect 4 Season Retreat

8 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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Lakefront Windham Area Home w/ Pool, Boat & Dock!, holiday rental in Preston Hollow

Lakefront Windham Area Home w/ Pool, Boat & Dock!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Meadows, Birdsong, Peace and Quiet, holiday rental in Preston Hollow

Meadows, Birdsong, Peace and Quiet

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Spacious House - 1 Mi. to Windham Ski Resort!, holiday rental in Preston Hollow

Spacious House - 1 Mi. to Windham Ski Resort!

5 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Tentrr Signature Site - Bearkill Brook, holiday rental in Preston Hollow

Tentrr Signature Site - Bearkill Brook

1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
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Tentrr Signature Site - Creekside Thyme, holiday rental in Preston Hollow

Tentrr Signature Site - Creekside Thyme

1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
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Tentrr Signature Site - Renew Yourself Renew the Earth, holiday rental in Preston Hollow

Tentrr Signature Site - Renew Yourself Renew the Earth

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Catskills Home, 5 Mins to Windham Mtn Resort!, holiday rental in Preston Hollow

Catskills Home, 5 Mins to Windham Mtn Resort!

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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The Country Place Resort Home of Zoom Flume Water park, holiday rental in Preston Hollow

The Country Place Resort Home of Zoom Flume Water park

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Chateau Tina Tiny Luxury Cabin Sleeps 6 Dog Friendly, holiday rental in Preston Hollow

Chateau Tina Tiny Luxury Cabin Sleeps 6 Dog Friendly

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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VILLA MARIE Luxury Cabin from our Tiny Cabin Collection Dogs ok, holiday rental in Preston Hollow

VILLA MARIE Luxury Cabin from our Tiny Cabin Collection Dogs ok

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Cabin  Sleeps 2  Dog Friendly, holiday rental in Preston Hollow

Cozy Cabin Sleeps 2 Dog Friendly

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Windham Mtn Home w/Deck & BBQ: ~3 Mi to Zoom Flume, holiday rental in Preston Hollow

Windham Mtn Home w/Deck & BBQ: ~3 Mi to Zoom Flume

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Moon Song Farm, holiday rental in Preston Hollow

Tentrr Signature Site - Moon Song Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! High Peak Heaven: Cozy Log Cabin on 1 Acre!, holiday rental in Preston Hollow

NEW! High Peak Heaven: Cozy Log Cabin on 1 Acre!

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Clean Condo w/ Loft 2 Mi to Windham Mountain Ski!, holiday rental in Preston Hollow

Clean Condo w/ Loft 2 Mi to Windham Mountain Ski!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Catskill Mtn Home w/ Deck ~ 1 Miles to Zoom Flume!, holiday rental in Preston Hollow

Catskill Mtn Home w/ Deck ~ 1 Miles to Zoom Flume!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Home w/ Sauna & Fire Pit: 13 Miles to Windham Mtn!, holiday rental in Preston Hollow

Home w/ Sauna & Fire Pit: 13 Miles to Windham Mtn!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Updated Catskills Mtn. Retreat w/ Panoramic Views!, holiday rental in Preston Hollow

Updated Catskills Mtn. Retreat w/ Panoramic Views!

3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Cozy Catskill Condo - 2 Mi to Windham Mountain Ski, holiday rental in Preston Hollow

Cozy Catskill Condo - 2 Mi to Windham Mountain Ski

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Peaceful Family Condo w/Deck + Mountain View!, holiday rental in Preston Hollow

NEW! Peaceful Family Condo w/Deck + Mountain View!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury Home w/ Deck: Explore the Catskill Mtns!, holiday rental in Preston Hollow

Luxury Home w/ Deck: Explore the Catskill Mtns!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Locust Grove, holiday rental in Preston Hollow

Tentrr Signature Site - Locust Grove

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Cozy Catskills Getaway w/ Yard & Mtn Views!, holiday rental in Preston Hollow

NEW! Cozy Catskills Getaway w/ Yard & Mtn Views!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Stylish Mtn Escape w/ Hot Tub, 3 Miles to Ski, holiday rental in Preston Hollow

NEW! Stylish Mtn Escape w/ Hot Tub, 3 Miles to Ski

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Modern & Cozy Windham Mountain Home: Hike & Tennis, holiday rental in Preston Hollow

Modern & Cozy Windham Mountain Home: Hike & Tennis

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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NEW! Catskills Home: Ponds, Tennis + Movie Theater, holiday rental in Preston Hollow

NEW! Catskills Home: Ponds, Tennis + Movie Theater

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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5 Min to Windham Mtn! Luxury Retreat w/Amazing Views! Natural Swimming Pond, holiday rental in Preston Hollow

5 Min to Windham Mtn! Luxury Retreat w/Amazing Views! Natural Swimming Pond

8 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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NEW! Quiet Upstate Escape < 10 Mi to Windham Mtn!, holiday rental in Preston Hollow

NEW! Quiet Upstate Escape < 10 Mi to Windham Mtn!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Spacious Durham Home w/ Separate Living Areas, holiday rental in Preston Hollow

NEW! Spacious Durham Home w/ Separate Living Areas

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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