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Smallwood Holiday Rentals

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50 rentals in Smallwood.
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Modern Luxury Catskills Lakefront Home, holiday rental in Smallwood

Modern Luxury Catskills Lakefront Home

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful woodland cabin with all new furniture, linens, electronics, appliances, holiday rental in Smallwood

Beautiful woodland cabin with all new furniture, linens, electronics, appliances

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Swinging Bridge Sanctuary, holiday rental in Smallwood

Tentrr Signature Site - Swinging Bridge Sanctuary

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Cottage in the Hamlet of Smallwood, holiday rental in Smallwood

Cozy Cottage in the Hamlet of Smallwood

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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NEW! Smallwood Oasis w/ 2 Bikes & Private Hot Tub!, holiday rental in Smallwood

NEW! Smallwood Oasis w/ 2 Bikes & Private Hot Tub!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Family Home w/ Large Yard: 1 Mi to White Lake, holiday rental in Smallwood

NEW! Family Home w/ Large Yard: 1 Mi to White Lake

1 bedroom
2 bathrooms
Sleeps 9
Match: Sleeps
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Warm Comfortable Getaway for Family & Friends., holiday rental in Smallwood

Warm Comfortable Getaway for Family & Friends.

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Luxe Country Home in the Swinging Bridge Lake Community, holiday rental in Smallwood

Luxe Country Home in the Swinging Bridge Lake Community

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Home on White Lake in Bethel, NY, holiday rental in Smallwood

Waterfront Home on White Lake in Bethel, NY

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Perry Pond Paradise!, holiday rental in Smallwood

Perry Pond Paradise!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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“The Oasis’”  Beautiful private lake front home with In-ground pool and sauna., holiday rental in Smallwood

“The Oasis’” Beautiful private lake front home with In-ground pool and sauna.

4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Spacious Catskills Home Sleeps 12 in Swinging Bridge Lake Community, holiday rental in Smallwood

Spacious Catskills Home Sleeps 12 in Swinging Bridge Lake Community

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Bethel Woods Getaway/ Hunting Cabin, holiday rental in Smallwood

Bethel Woods Getaway/ Hunting Cabin

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Large Modern Cabin with Hot Tub Tucked in Woods, holiday rental in Smallwood

Large Modern Cabin with Hot Tub Tucked in Woods

5 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
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Enjoy the Magic of the Catskills in your Private Lakefront Home, holiday rental in Smallwood

Enjoy the Magic of the Catskills in your Private Lakefront Home

2 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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The Homestead: 14 bedroom lakehouse in scenic Catskills town by Red Cottage Inc., holiday rental in Smallwood

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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This beautiful location will warm your hearts and make your stay all the more pl, holiday rental in Smallwood

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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Indian Stone Property with 4 Bedroom House, holiday rental in Smallwood

Indian Stone Property with 4 Bedroom House

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Woodstock Way Vacation and Concert Rentals, holiday rental in Smallwood

Woodstock Way Vacation and Concert Rentals

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Floating Farmhouse: Stunning renovation in storybook setting, 2 hours from NYC, holiday rental in Smallwood

Floating Farmhouse: Stunning renovation in storybook setting, 2 hours from NYC

5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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NEW! Luxe Lakefront Family Cottage w/ Private Dock, holiday rental in Smallwood

NEW! Luxe Lakefront Family Cottage w/ Private Dock

9 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Private Catskills Retreat w/ Pond, Yard & More!, holiday rental in Smallwood

Private Catskills Retreat w/ Pond, Yard & More!

6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Catskills Vacation Estate, holiday rental in Smallwood

Catskills Vacation Estate

4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Catskills Luxury Lake House - New York, United States, holiday rental in Smallwood

Catskills Luxury Lake House - New York, United States

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Contemporary Lake Front - 5 Acres!, holiday rental in Smallwood

Contemporary Lake Front - 5 Acres!

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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3 bedrooms,  2.5 baths  fully furnished and equipped, dog-friendly, on 15 acres, holiday rental in Smallwood

3 bedrooms, 2.5 baths fully furnished and equipped, dog-friendly, on 15 acres

3 bedrooms
3 bathrooms
Sleeps 1
Match: Sleeps
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Tentrr Signature Site - Fields of Dreams at Callicoon, holiday rental in Smallwood

Tentrr Signature Site - Fields of Dreams at Callicoon

1 bedroom
1 bathroom
Sleeps 14
Match: Sleeps
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Tentrr Signature Site - Hemlock Ridge, holiday rental in Smallwood

Tentrr Signature Site - Hemlock Ridge

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Beautiful Country Home, holiday rental in Smallwood

Beautiful Country Home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Hemlock Ridge, holiday rental in Smallwood

Tentrr Signature Site - Hemlock Ridge

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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In the clouds your cozy- lake house ( 2 hrs from NYC), holiday rental in Smallwood

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Quiet 4 Bedroom House with Lake Views on large field - perfect for family breaks, holiday rental in Smallwood

Quiet 4 Bedroom House with Lake Views on large field - perfect for family breaks

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Catskill mountain getaway, holiday rental in Smallwood

Catskill mountain getaway

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cozy Lakeside Cottage with Spacious Deck & Grill!, holiday rental in Smallwood

Cozy Lakeside Cottage with Spacious Deck & Grill!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Fall Fun!  Lake Home on private Highland Lake across the road., holiday rental in Smallwood

Fall Fun! Lake Home on private Highland Lake across the road.

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Pond View, holiday rental in Smallwood

Tentrr Signature Site - Pond View

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Bright Swan Lake Getaway w/ Canoe & Hot Tub!, holiday rental in Smallwood

NEW! Bright Swan Lake Getaway w/ Canoe & Hot Tub!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Modern Monticello Home w/ Hot Tub on 17 Acres, holiday rental in Smallwood

NEW! Modern Monticello Home w/ Hot Tub on 17 Acres

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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NEW! Cozy Swan Lake Apt w/ Grill + Private Hot Tub, holiday rental in Smallwood

NEW! Cozy Swan Lake Apt w/ Grill + Private Hot Tub

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NEW! Charming Swan Lake Apt w/ Deck + Game Room!, holiday rental in Smallwood

NEW! Charming Swan Lake Apt w/ Deck + Game Room!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Spacious Sullivan County House w/ Fire Pit, holiday rental in Smallwood

NEW! Spacious Sullivan County House w/ Fire Pit

1 bedroom
2 bathrooms
Sleeps 10
Match: Sleeps
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Tentrr Signature Site - Say Hello 2 Heaven at the Tentrr Catskill Retreat, holiday rental in Smallwood

Tentrr Signature Site - Say Hello 2 Heaven at the Tentrr Catskill Retreat

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Come As You Are at the Tentrr Catskill Retreat - Single, holiday rental in Smallwood

Tentrr Signature Site - Come As You Are at the Tentrr Catskill Retreat - Single

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Ramble On at the Tentrr Catskill Retreat - Single Camp, holiday rental in Smallwood

Tentrr Signature Site - Ramble On at the Tentrr Catskill Retreat - Single Camp

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Wildflowers at the Tentrr Catskill Retreat - Single Camp, holiday rental in Smallwood

Tentrr Signature Site - Wildflowers at the Tentrr Catskill Retreat - Single Camp

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Go Your Own Way at the Tentrr Catskill Retreat - Single, holiday rental in Smallwood

Tentrr Signature Site - Go Your Own Way at the Tentrr Catskill Retreat - Single

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - R2 at the Tentrr Catskill Retreat - Double Camp with, holiday rental in Smallwood

Tentrr Signature Site - R2 at the Tentrr Catskill Retreat - Double Camp with

2 bedrooms
1 bathroom
Sleeps 16
Match: Sleeps
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Tentrr Signature Site - Purple Haze at the Tentrr Catskill Retreat - Single Camp, holiday rental in Smallwood

Tentrr Signature Site - Purple Haze at the Tentrr Catskill Retreat - Single Camp

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Twin Creeks Campsite, holiday rental in Smallwood

Tentrr Signature Site - Twin Creeks Campsite

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Unique Catskills Hideaway - Walk to Lake Jeff, holiday rental in Smallwood

NEW! Unique Catskills Hideaway - Walk to Lake Jeff

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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