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Callicoon Holiday Rentals

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50 rentals in Callicoon.
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Western Sullivan country home, beautiful views, holiday rental in Callicoon

Western Sullivan country home, beautiful views

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Spacious Home w/ Deck, Grill & Delaware River View, holiday rental in Callicoon

Spacious Home w/ Deck, Grill & Delaware River View

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming House Secluded in a 4-Acre Parcel with View, holiday rental in Callicoon

Charming House Secluded in a 4-Acre Parcel with View

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Enjoy Charming & Private Delaware Riverfront Home near Callicoon NY, holiday rental in Callicoon

Enjoy Charming & Private Delaware Riverfront Home near Callicoon NY

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Secluded modern log cabin with charming private water fall on 12 acres!, holiday rental in Callicoon

Secluded modern log cabin with charming private water fall on 12 acres!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Roomy Lakeside Home With Great Views And Minutes From Trout Town USA (Roscoe), holiday rental in Callicoon

Roomy Lakeside Home With Great Views And Minutes From Trout Town USA (Roscoe)

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Majestic Farmland A-Frame with Sweeping Views, holiday rental in Callicoon

Majestic Farmland A-Frame with Sweeping Views

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Long Eddy Cabin w/ Fire Pit + Game Room!, holiday rental in Callicoon

Cozy Long Eddy Cabin w/ Fire Pit + Game Room!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Hilltop Lodge, a Modern Seasonal Retreat in the Poconos!, holiday rental in Callicoon

Hilltop Lodge, a Modern Seasonal Retreat in the Poconos!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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French Woods Farm near Callicoon NY welcomes you, holiday rental in Callicoon

French Woods Farm near Callicoon NY welcomes you

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Log Cabin On Paradise Pond, Spring Wonders, Summer Fun & Fall Foliage, holiday rental in Callicoon

The Log Cabin On Paradise Pond, Spring Wonders, Summer Fun & Fall Foliage

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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COZY COTTAGE LOCATED ON DELAWARE RIVER, holiday rental in Callicoon

COZY COTTAGE LOCATED ON DELAWARE RIVER

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Perry Pond Paradise!, holiday rental in Callicoon

Perry Pond Paradise!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Damascus Luxury Log Cabin, holiday rental in Callicoon

Damascus Luxury Log Cabin

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Mid Century Modern Ranch in Catskills Near River, holiday rental in Callicoon

Mid Century Modern Ranch in Catskills Near River

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Work remotely in fresh mountain air! Pet friendly!, holiday rental in Callicoon

Work remotely in fresh mountain air! Pet friendly!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Rustic Modern Catskills Cottage, holiday rental in Callicoon

Rustic Modern Catskills Cottage

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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The Homestead: 14 bedroom lakehouse in scenic Catskills town by Red Cottage Inc., holiday rental in Callicoon

The Homestead: 14 bedroom lakehouse in scenic Catskills town by Red Cottage Inc.

14 bedrooms
11 bathrooms
Sleeps 28
Match: Sleeps
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The Blue Hill House!, holiday rental in Callicoon

The Blue Hill House!

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Nana’s house is the perfect country getaway., holiday rental in Callicoon

Nana’s house is the perfect country getaway.

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Bethel Woods Getaway/ Hunting Cabin, holiday rental in Callicoon

Bethel Woods Getaway/ Hunting Cabin

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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This beautiful location will warm your hearts and make your stay all the more pl, holiday rental in Callicoon

This beautiful location will warm your hearts and make your stay all the more pl

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Get away! Work remotely strong WiFi, pets okay!, holiday rental in Callicoon

Get away! Work remotely strong WiFi, pets okay!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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*Log Cabin * Hot Tub * Sauna * Private Pond * 23 acres * 4.6 mi Bethel Woods, holiday rental in Callicoon

*Log Cabin * Hot Tub * Sauna * Private Pond * 23 acres * 4.6 mi Bethel Woods

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Lenapehoking Farm, holiday rental in Callicoon

Tentrr Signature Site - Lenapehoking Farm

1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
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NEW! Private Catskills Retreat w/Pond, Yard & More, holiday rental in Callicoon

NEW! Private Catskills Retreat w/Pond, Yard & More

6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Come Enjoy Sullivan County's Catskills, Lake Communirty Swiss Chalet Availablle for Fall and Winter Rentals, holiday rental in Callicoon

Come Enjoy Sullivan County's Catskills, Lake Communirty Swiss Chalet Availablle for Fall and Winter Rentals

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newly Built & Secluded Catskill Cottage w/ Views!, holiday rental in Callicoon

Newly Built & Secluded Catskill Cottage w/ Views!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2 bedroom duplex apartment walking distance to town, river, antiques, restaurant, holiday rental in Callicoon

2 bedroom duplex apartment walking distance to town, river, antiques, restaurant

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Modern Glass 3 Bedroom House on Delaware River for up to 6 Guests, holiday rental in Callicoon

Beautiful Modern Glass 3 Bedroom House on Delaware River for up to 6 Guests

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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'Hummingbird Farm' on 10 Acres near Hancock!, holiday rental in Callicoon

'Hummingbird Farm' on 10 Acres near Hancock!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Rustic Cabin w/Porch 15 Min to Delaware River, holiday rental in Callicoon

Rustic Cabin w/Porch 15 Min to Delaware River

2 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Livingston Manor Cabin w/Private Lake Access, holiday rental in Callicoon

Livingston Manor Cabin w/Private Lake Access

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Adams River Run, holiday rental in Callicoon

Tentrr Signature Site - Adams River Run

1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
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Tentrr Signature Site - Back 2 Nature Camp, holiday rental in Callicoon

Tentrr Signature Site - Back 2 Nature Camp

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Tentrr Signature Site - El Dorado Camp, holiday rental in Callicoon

Tentrr Signature Site - El Dorado Camp

1 bedroom
1 bathroom
Sleeps 16
Match: Sleeps
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Tentrr Signature Site - Fields of Dreams at Callicoon, holiday rental in Callicoon

Tentrr Signature Site - Fields of Dreams at Callicoon

1 bedroom
1 bathroom
Sleeps 14
Match: Sleeps
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Tentrr Signature Site - Poet's Skyrock Organic Farm, holiday rental in Callicoon

Tentrr Signature Site - Poet's Skyrock Organic Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Running W Retreat, holiday rental in Callicoon

Tentrr Signature Site - Running W Retreat

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Large 14 Bedroom Property, Great For Family Reunions!, holiday rental in Callicoon

Large 14 Bedroom Property, Great For Family Reunions!

14 bedrooms
9 bathrooms
Sleeps 32
Match: Sleeps
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Tentrr Signature Site - Adams River Run, holiday rental in Callicoon

Tentrr Signature Site - Adams River Run

2 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Tentrr Signature Site - Mountain Bliss Campsite, holiday rental in Callicoon

Tentrr Signature Site - Mountain Bliss Campsite

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Your private log home overlooking the Delaware River, holiday rental in Callicoon

Your private log home overlooking the Delaware River

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Ongdalsam healing village, holiday rental in Callicoon

Ongdalsam healing village

3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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In the clouds your cozy- lake house ( 2 hrs from NYC), holiday rental in Callicoon

In the clouds your cozy- lake house ( 2 hrs from NYC)

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic schoolhouse - disconnect from technology, holiday rental in Callicoon

Historic schoolhouse - disconnect from technology

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Pond View, holiday rental in Callicoon

Tentrr Signature Site - Pond View

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Major's Mountain Camp & Float, holiday rental in Callicoon

Tentrr Signature Site - Major's Mountain Camp & Float

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Pat's Perch Camp & Float, holiday rental in Callicoon

Tentrr Signature Site - Pat's Perch Camp & Float

1 bedroom
1 bathroom
Sleeps 7
Match: Sleeps
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Tentrr Signature Site - Paradise Falls, holiday rental in Callicoon

Tentrr Signature Site - Paradise Falls

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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