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Olivebridge Holiday Rentals

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50 rentals in Olivebridge.
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Charming, Tranquil Catskills Log Home., holiday rental in Olivebridge

Charming, Tranquil Catskills Log Home.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Ashokan Reservoir Retreat, holiday rental in Olivebridge

Tentrr Signature Site - Ashokan Reservoir Retreat

1 bedroom
1 bathroom
Sleeps 4
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It's Fall in the Hudson Valley!  Enjoy your private cottage, fireplace & hot tub, holiday rental in Olivebridge

It's Fall in the Hudson Valley! Enjoy your private cottage, fireplace & hot tub

0 bedrooms
1 bathroom
Sleeps 4
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SECLUDED POOL, SPA & STREAM on 7 Acres, JUST 5 MINUTES FROM TOWN, holiday rental in Olivebridge

SECLUDED POOL, SPA & STREAM on 7 Acres, JUST 5 MINUTES FROM TOWN

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Pristine Mountaintop Log Cabin in Pine Forest, 1.5 Miles to Town!, holiday rental in Olivebridge

Pristine Mountaintop Log Cabin in Pine Forest, 1.5 Miles to Town!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Secluded Catskill Mountain Log Cabin, Breathtaking Vista, Private, Relaxing, holiday rental in Olivebridge

Secluded Catskill Mountain Log Cabin, Breathtaking Vista, Private, Relaxing

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Freshly Renovated Home in Catskills Sweet Spot!!!, holiday rental in Olivebridge

Freshly Renovated Home in Catskills Sweet Spot!!!

3 bedrooms
2 bathrooms
Sleeps 6
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Big House!  Lots of space for your family.  Enjoy the outdoors in the Catskills, holiday rental in Olivebridge

Big House! Lots of space for your family. Enjoy the outdoors in the Catskills

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Private 6 Acre Catskills Retreat Between Mohonk and Woodstock - Sleeps 8, holiday rental in Olivebridge

Private 6 Acre Catskills Retreat Between Mohonk and Woodstock - Sleeps 8

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Leggett Cottage, High Falls, NY., holiday rental in Olivebridge

Leggett Cottage, High Falls, NY.

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Hilltop Treehouse Woodstock Retreat, holiday rental in Olivebridge

Hilltop Treehouse Woodstock Retreat

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Relaxing Catskill Mountain Cottage. Light filled. Central to Hiking and skiing., holiday rental in Olivebridge

Relaxing Catskill Mountain Cottage. Light filled. Central to Hiking and skiing.

2 bedrooms
1 bathroom
Sleeps 4
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COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!, holiday rental in Olivebridge

COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!

3 bedrooms
2 bathrooms
Sleeps 6
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Romantic Country Barn By the Stream, holiday rental in Olivebridge

Romantic Country Barn By the Stream

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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A Country Home in Hurley, New York, holiday rental in Olivebridge

A Country Home in Hurley, New York

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded, Zen, Luxurious Stone Ridge Country Home, holiday rental in Olivebridge

Secluded, Zen, Luxurious Stone Ridge Country Home

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace, holiday rental in Olivebridge

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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A Tranquil & Relaxing Space, holiday rental in Olivebridge

A Tranquil & Relaxing Space

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Mid century modern catskill home set in the south of catskill park., holiday rental in Olivebridge

Mid century modern catskill home set in the south of catskill park.

3 bedrooms
2 bathrooms
Sleeps 6
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with mountain views, minutes from Woodstock, NY, holiday rental in Olivebridge

with mountain views, minutes from Woodstock, NY

4 bedrooms
4 bathrooms
Sleeps 6
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New Hot Tub & Heated Pool in Prime Woodstock Gut Renovated Modern Home, holiday rental in Olivebridge

New Hot Tub & Heated Pool in Prime Woodstock Gut Renovated Modern Home

5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Gorgeous Villa w/ Mountain Views, pool, hot tub!, holiday rental in Olivebridge

Gorgeous Villa w/ Mountain Views, pool, hot tub!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Mid Century Ranch-Hot Tub-Minutes to Center ofTown, holiday rental in Olivebridge

Mid Century Ranch-Hot Tub-Minutes to Center ofTown

4 bedrooms
4 bathrooms
Sleeps 8
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Woodstock Mediterranean Retreat, holiday rental in Olivebridge

Woodstock Mediterranean Retreat

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Ashokan Reservior Barn Style home, holiday rental in Olivebridge

Ashokan Reservior Barn Style home

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Luxe Bohemian Cabin, Secluded, 6 min to Woodstock, holiday rental in Olivebridge

Luxe Bohemian Cabin, Secluded, 6 min to Woodstock

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Enjoy the beauty of spring in the Catskills near New Paltz, holiday rental in Olivebridge

Enjoy the beauty of spring in the Catskills near New Paltz

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Woodstock Stone Cottage Swim Lake 3 ski resorts fishing hiking biking music arts, holiday rental in Olivebridge

Woodstock Stone Cottage Swim Lake 3 ski resorts fishing hiking biking music arts

4 bedrooms
2 bathrooms
Sleeps 8
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Teahouse Cottage, holiday rental in Olivebridge

Teahouse Cottage

50 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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1972 Airtream in the beautiful Hudson Valley Serene - weekly and motnhly rates, holiday rental in Olivebridge

1972 Airtream in the beautiful Hudson Valley Serene - weekly and motnhly rates

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Kingston/Hurley woodland house, holiday rental in Olivebridge

Kingston/Hurley woodland house

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Glamping at Woodstock Meadows - Outdoor B&B (2 secluded tents w/amenities), holiday rental in Olivebridge

Glamping at Woodstock Meadows - Outdoor B&B (2 secluded tents w/amenities)

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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country retreat with a modern edge, holiday rental in Olivebridge

country retreat with a modern edge

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Camp AnuLyfe: Treat yourself with our extras for a, holiday rental in Olivebridge

Tentrr Signature Site - Camp AnuLyfe: Treat yourself with our extras for a

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Newtown Pippin, holiday rental in Olivebridge

Tentrr Signature Site - Newtown Pippin

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Osa Trail, holiday rental in Olivebridge

Tentrr Signature Site - Osa Trail

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Sundown for big game hunting, holiday rental in Olivebridge

Tentrr Signature Site - Sundown for big game hunting

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Stonecutters Ledge, holiday rental in Olivebridge

Tentrr Signature Site - Stonecutters Ledge

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Yankeetown Pond Peace of Mind, holiday rental in Olivebridge

Tentrr Signature Site - Yankeetown Pond Peace of Mind

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Historic stone house in the heart of the Gunks. Modern luxury getaway., holiday rental in Olivebridge

Historic stone house in the heart of the Gunks. Modern luxury getaway.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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*ASHTON HILLS Estate -7B/4Ba Luxury Woodstock NY*, holiday rental in Olivebridge

*ASHTON HILLS Estate -7B/4Ba Luxury Woodstock NY*

7 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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5 Bedroom Rustic Country Home, holiday rental in Olivebridge

5 Bedroom Rustic Country Home

5 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Work from home, in our home. Mid-century cottage in the heart of the Catskills, holiday rental in Olivebridge

Work from home, in our home. Mid-century cottage in the heart of the Catskills

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Orchard Tent Overlooking Mohonk   Golden Russet, holiday rental in Olivebridge

Tentrr Signature Site - Orchard Tent Overlooking Mohonk Golden Russet

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Ancient Oak in Historic Orchard   Northern Spy, holiday rental in Olivebridge

Tentrr Signature Site - Ancient Oak in Historic Orchard Northern Spy

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Orchard Tent Esopus, holiday rental in Olivebridge

Tentrr Signature Site - Orchard Tent Esopus

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Lakeside Tents in Historic Orchard, holiday rental in Olivebridge

Tentrr Signature Site - Lakeside Tents in Historic Orchard

2 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Cliff Haven In The Catskills, holiday rental in Olivebridge

Cliff Haven In The Catskills

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Tentrr Signature Site - Lower Pond Tent, holiday rental in Olivebridge

Tentrr Signature Site - Lower Pond Tent

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Sioux Tipi on the waterfall, holiday rental in Olivebridge

Sioux Tipi on the waterfall

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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