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Olivebridge Vacation Rentals

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

Tentrr Signature Site - Ashokan Reservoir Retreat

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

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

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

Freshly Renovated Home in Catskills Sweet Spot!!!

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

Leggett Cottage, High Falls, NY.

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

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

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

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Romantic Country Barn By the Stream, vacation 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, vacation 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, vacation 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, vacation 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, vacation 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., vacation rental in Olivebridge

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

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

with mountain views, minutes from Woodstock, NY

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

Mid Century Ranch-Hot Tub-Minutes to Center ofTown

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Woodstock Mediterranean Retreat, vacation rental in Olivebridge

Woodstock Mediterranean Retreat

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

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Teahouse Cottage, vacation 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, vacation 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, vacation 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), vacation 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, vacation 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, vacation 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, vacation 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, vacation rental in Olivebridge

Tentrr Signature Site - Osa Trail

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Sundown, vacation rental in Olivebridge

Tentrr Signature Site - Sundown

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

5 Bedroom Rustic Country Home

5 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Tentrr Signature Site - Orchard Tent Overlooking Mohonk   Golden Russet, vacation 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, vacation 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, vacation 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, vacation rental in Olivebridge

Tentrr Signature Site - Lakeside Tents in Historic Orchard

2 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Catskills home overlooking the High Peaks, vacation rental in Olivebridge

Catskills home overlooking the High Peaks

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Cliff Haven In The Catskills, vacation 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, vacation 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, vacation rental in Olivebridge

Sioux Tipi on the waterfall

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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