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Oak Hill Holiday Rentals

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49 rentals in Oak Hill.
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NEW! Home w/Sauna & Fire Pit, 13 Mi to Windham Mtn, holiday rental in Oak Hill

NEW! Home w/Sauna & Fire Pit, 13 Mi to Windham Mtn

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub, holiday rental in Oak Hill

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 Oak Hill

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 Oak Hill

*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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Winsome Windham - Secluded Chalet with Ski Windham Views, holiday rental in Oak Hill

Winsome Windham - Secluded Chalet with Ski Windham Views

4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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The perfect mountain getaway nestled in the woods 2 min from downtown Windham., holiday rental in Oak Hill

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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'New Home' Idyllic  Mt Views ,Pond & Horse farm views 2 min to Town, holiday rental in Oak Hill

'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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Beautiful Home, Gorgeous View, Spacious Living, holiday rental in Oak Hill

Beautiful Home, Gorgeous View, Spacious Living

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Mountain House Retreat, holiday rental in Oak Hill

Mountain House Retreat

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Chalet with a Pond and Pool with  Spectacular views of the Catskill Mountains, holiday rental in Oak Hill

Chalet with a Pond and Pool with Spectacular views of the Catskill Mountains

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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FAB FUN GREEN BUILT FARMHOUSE ON 17 ACRES, holiday rental in Oak Hill

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 Oak Hill

Secluded Charming Water Front Log Home

4 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Year-Round Relaxing Mountain Escape, holiday rental in Oak Hill

Year-Round Relaxing Mountain Escape

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Mandeville Manor, “Beautiful Fall Foliage”!!!, holiday rental in Oak Hill

Mandeville Manor, “Beautiful Fall Foliage”!!!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Spacious Mountain Escape - Minutes to Windham/Hunter, holiday rental in Oak Hill

Spacious Mountain Escape - Minutes to Windham/Hunter

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Great 5 BR House !!!!, holiday rental in Oak Hill

Great 5 BR House !!!!

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Windham Skiers Book Now! Cottage North Catskills, holiday rental in Oak Hill

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 Oak Hill

Historic Catskill Mountain House close to Windham

7 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Armstrongs Elk Farm, holiday rental in Oak Hill

Armstrongs Elk Farm

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Windham Mountain Ski House with Great Views, holiday rental in Oak Hill

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 Oak Hill

The Mountain House: The Perfect 4 Season Retreat

8 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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Mountain views and seclusion in a rustic midcentury home on Catskill Creek., holiday rental in Oak Hill

Mountain views and seclusion in a rustic midcentury home on Catskill Creek.

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Brand new 4-bedroom ski chalet with bucolic mountain, lake and meadow views., holiday rental in Oak Hill

Brand new 4-bedroom ski chalet with bucolic mountain, lake and meadow views.

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lakefront Windham Area Home w/ Pool, Boat & Dock!, holiday rental in Oak Hill

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 Oak Hill

Meadows, Birdsong, Peace and Quiet

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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The Xenia, holiday rental in Oak Hill

The Xenia

4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Tentrr Signature Site - Camp Creekside, holiday rental in Oak Hill

Tentrr Signature Site - Camp Creekside

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Creekside Thyme, holiday rental in Oak Hill

Tentrr Signature Site - Creekside Thyme

1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
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Tentrr Signature Site - Creekside Zen in Catskills, holiday rental in Oak Hill

Tentrr Signature Site - Creekside Zen in Catskills

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Catskills Home, 5 Mins to Windham Mtn Resort!, holiday rental in Oak Hill

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 Oak Hill

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 Oak Hill

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 Oak Hill

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 Oak Hill

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 Oak Hill

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 Oak Hill

Tentrr Signature Site - Moon Song Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Garden Room Suite at the Van Winkle Inn, holiday rental in Oak Hill

Garden Room Suite at the Van Winkle Inn

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Turner Suite, holiday rental in Oak Hill

Turner Suite

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Peggy Madeline Suite at the Van Winkle Inn, holiday rental in Oak Hill

The Peggy Madeline Suite at the Van Winkle Inn

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Castle Family Suite, holiday rental in Oak Hill

The Castle Family Suite

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Hannah Suite at the Van Winkle Inn, holiday rental in Oak Hill

The Hannah Suite at the Van Winkle Inn

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NEW! High Peak Heaven: Cozy Log Cabin on 1 Acre!, holiday rental in Oak Hill

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

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Catskill Mtn Home w/ Deck ~ 1 Miles to Zoom Flume!, holiday rental in Oak Hill

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Updated Catskills Mtn. Retreat w/ Panoramic Views!, holiday rental in Oak Hill

Updated Catskills Mtn. Retreat w/ Panoramic Views!

3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Luxury Home w/ Deck: Explore the Catskill Mtns!, holiday rental in Oak Hill

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 Oak Hill

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 Oak Hill

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 Oak Hill

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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Modern & Cozy Windham Mtn House - Hike & Ski!, holiday rental in Oak Hill

NEW! Modern & Cozy Windham Mtn House - Hike & Ski!

6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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