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Holiday Homes in Samsonville

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50 rentals in Samsonville.
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Tentrr Signature Site - Tabasco Woods (Two tent site), holiday rental in Samsonville

Tentrr Signature Site - Tabasco Woods (Two tent site)

2 bedrooms
1 bathroom
Sleeps 8
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Enjoy the beauty of spring in the Catskills near New Paltz, holiday rental in Samsonville

Enjoy the beauty of spring in the Catskills near New Paltz

2 bedrooms
1 bathroom
Sleeps 4
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Tentrr Signature Site - Tabasco Woods II (Two tent site), holiday rental in Samsonville

Tentrr Signature Site - Tabasco Woods II (Two tent site)

2 bedrooms
1 bathroom
Sleeps 8
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Tentrr Signature Site - Osa Trail, holiday rental in Samsonville

Tentrr Signature Site - Osa Trail

1 bedroom
1 bathroom
Sleeps 6
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Tentrr Signature Site - Sundown, holiday rental in Samsonville

Tentrr Signature Site - Sundown

1 bedroom
1 bathroom
Sleeps 4
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Modern Catskills Mountain Retreat Filled With Natural Light, holiday rental in Samsonville

Modern Catskills Mountain Retreat Filled With Natural Light

3 bedrooms
3 bathrooms
Sleeps 6
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Best view  of a 1,000 acre forest.  Two hundred plus  five star reviews!, holiday rental in Samsonville

Best view of a 1,000 acre forest. Two hundred plus five star reviews!

2 bedrooms
1 bathroom
Sleeps 4
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Charming, Tranquil Catskills Log Home., holiday rental in Samsonville

Charming, Tranquil Catskills Log Home.

2 bedrooms
1 bathroom
Sleeps 4
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Secluded Catskill Mountain Log Cabin, Breathtaking Vista, Private, Relaxing, holiday rental in Samsonville

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

4 bedrooms
3 bathrooms
Sleeps 15
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Blue Springs; secluded paradise bordering Minnewaska State Park, holiday rental in Samsonville

Blue Springs; secluded paradise bordering Minnewaska State Park

3 bedrooms
3 bathrooms
Sleeps 8
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Leggett Cottage, High Falls, NY., holiday rental in Samsonville

Leggett Cottage, High Falls, NY.

1 bedroom
1 bathroom
Sleeps 2
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Hilltop Treehouse Woodstock Retreat, holiday rental in Samsonville

Hilltop Treehouse Woodstock Retreat

3 bedrooms
2 bathrooms
Sleeps 8
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Private 6 Acre Catskills Retreat Between Mohonk and Woodstock - Sleeps 8, holiday rental in Samsonville

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

3 bedrooms
3 bathrooms
Sleeps 8
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Spacious/Secluded Home w/Pool, Chefs Kitchen, Neighboring Farm Pastoral Views., holiday rental in Samsonville

Spacious/Secluded Home w/Pool, Chefs Kitchen, Neighboring Farm Pastoral Views.

5 bedrooms
3 bathrooms
Sleeps 10
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Relaxing Catskill Mountain Cottage. Light filled. Central to Hiking and skiing., holiday rental in Samsonville

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

2 bedrooms
1 bathroom
Sleeps 4
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Romantic Country Barn By the Stream, holiday rental in Samsonville

Romantic Country Barn By the Stream

2 bedrooms
1 bathroom
Sleeps 4
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NEW! Architect-designed luxury “Tree House” on ridge w/mtn + reservoir views, holiday rental in Samsonville

NEW! Architect-designed luxury “Tree House” on ridge w/mtn + reservoir views

4 bedrooms
3 bathrooms
Sleeps 8
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A Tranquil & Relaxing Space, holiday rental in Samsonville

A Tranquil & Relaxing Space

1 bedroom
1 bathroom
Sleeps 4
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Secluded, Zen, Luxurious Stone Ridge Country Home, holiday rental in Samsonville

Secluded, Zen, Luxurious Stone Ridge Country Home

3 bedrooms
3 bathrooms
Sleeps 12
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Mid century modern catskill home set in the south of catskill park., holiday rental in Samsonville

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 Samsonville

with mountain views, minutes from Woodstock, NY

4 bedrooms
4 bathrooms
Sleeps 6
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Architect-designed Modern Cabin retreat, holiday rental in Samsonville

Architect-designed Modern Cabin retreat

3 bedrooms
3 bathrooms
Sleeps 6
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Ashokan Reservior Barn Style home, holiday rental in Samsonville

Ashokan Reservior Barn Style home

2 bedrooms
1 bathroom
Sleeps 5
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Woodstock Stone Cottage Swim Lake 3 ski resorts fishing hiking biking music arts, holiday rental in Samsonville

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

4 bedrooms
2 bathrooms
Sleeps 8
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1972 Airtream in the beautiful Hudson Valley Serene - weekly and motnhly rates, holiday rental in Samsonville

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

1 bedroom
1 bathroom
Sleeps 2
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Tranquil Retreat Stunning Views+Hot Tub, Woodstock Area-Glenford House, holiday rental in Samsonville

Tranquil Retreat Stunning Views+Hot Tub, Woodstock Area-Glenford House

3 bedrooms
2 bathrooms
Sleeps 6
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Blue Stone Creek Side Cottage, holiday rental in Samsonville

Blue Stone Creek Side Cottage

3 bedrooms
2 bathrooms
Sleeps 5
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country retreat with a modern edge, holiday rental in Samsonville

country retreat with a modern edge

3 bedrooms
1 bathroom
Sleeps 6
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Updated/Pet-Friendly Cabin By Hikes and Woodstock!, holiday rental in Samsonville

Updated/Pet-Friendly Cabin By Hikes and Woodstock!

2 bedrooms
1 bathroom
Sleeps 3
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Tentrr Signature Site - Dogwood Tree Camp, holiday rental in Samsonville

Tentrr Signature Site - Dogwood Tree Camp

1 bedroom
1 bathroom
Sleeps 4
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Tentrr Signature Site - Newtown Pippin, holiday rental in Samsonville

Tentrr Signature Site - Newtown Pippin

1 bedroom
1 bathroom
Sleeps 6
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Tentrr Signature Site - Starlight Starbright, holiday rental in Samsonville

Tentrr Signature Site - Starlight Starbright

1 bedroom
1 bathroom
Sleeps 4
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Tentrr Signature Site - Yankeetown Pond Peace of Mind, holiday rental in Samsonville

Tentrr Signature Site - Yankeetown Pond Peace of Mind

1 bedroom
1 bathroom
Sleeps 8
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Tentrr Signature Site - Mini Yosemite in the Hudson Valley, holiday rental in Samsonville

Tentrr Signature Site - Mini Yosemite in the Hudson Valley

1 bedroom
1 bathroom
Sleeps 4
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The Blue House, holiday rental in Samsonville

The Blue House

3 bedrooms
2 bathrooms
Sleeps 6
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Historic stone house in the heart of the Gunks. Modern luxury getaway., holiday rental in Samsonville

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

3 bedrooms
2 bathrooms
Sleeps 6
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NEW! Family Home w/Deck Near Minnewaska State Park, holiday rental in Samsonville

NEW! Family Home w/Deck Near Minnewaska State Park

3 bedrooms
3 bathrooms
Sleeps 9
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NEW! Spacious Stone Ridge Home on 6 Private Acres!, holiday rental in Samsonville

NEW! Spacious Stone Ridge Home on 6 Private Acres!

8 bedrooms
3 bathrooms
Sleeps 10
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*ASHTON HILLS Estate -7B/4Ba Luxury Woodstock NY*, holiday rental in Samsonville

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

7 bedrooms
4 bathrooms
Sleeps 16
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Work from home, in our home. Mid-century cottage in the heart of the Catskills, holiday rental in Samsonville

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

2 bedrooms
1 bathroom
Sleeps 4
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Catskills farmhouse with wraparound porch, pool and views., holiday rental in Samsonville

Catskills farmhouse with wraparound porch, pool and views.

5 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Tentrr Signature Site - Reservoir Retreat, holiday rental in Samsonville

Tentrr Signature Site - Reservoir Retreat

1 bedroom
1 bathroom
Sleeps 4
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Tentrr Signature Site - Ashokan Reservoir Retreat, holiday rental in Samsonville

Tentrr Signature Site - Ashokan Reservoir Retreat

1 bedroom
1 bathroom
Sleeps 4
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Tentrr Signature Site - Orchard Tent Overlooking Mohonk   Golden Russet, holiday rental in Samsonville

Tentrr Signature Site - Orchard Tent Overlooking Mohonk Golden Russet

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

Tentrr Signature Site - Ancient Oak in Historic Orchard Northern Spy

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

Tentrr Signature Site - Orchard Tent Esopus

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

Tentrr Signature Site - Lakeside Tents in Historic Orchard

2 bedrooms
1 bathroom
Sleeps 10
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Tentrr Signature Site - Sunrise Meadow, holiday rental in Samsonville

Tentrr Signature Site - Sunrise Meadow

1 bedroom
1 bathroom
Sleeps 4
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Mountain View Victorian with Convenient Location and  Lots of Space to Play, holiday rental in Samsonville

Mountain View Victorian with Convenient Location and Lots of Space to Play

5 bedrooms
2 bathrooms
Sleeps 8
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Tentrr Signature Site - Lower Pond Tent, holiday rental in Samsonville

Tentrr Signature Site - Lower Pond Tent

1 bedroom
1 bathroom
Sleeps 6
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