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Pawling Holiday Rentals

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50 rentals in Pawling.
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Serene, Peaceful Get-Away (Log Cabin by the Lake), holiday rental in Pawling

Serene, Peaceful Get-Away (Log Cabin by the Lake)

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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House on Appalachian Trail, walking distance from NYC trains. 3bd/1ba, 3 acres, holiday rental in Pawling

House on Appalachian Trail, walking distance from NYC trains. 3bd/1ba, 3 acres

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Secluded country cabin upstate New York, near  metro north train, holiday rental in Pawling

Secluded country cabin upstate New York, near metro north train

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Welcome to The Lake: Your Private Paradise Awaits!, holiday rental in Pawling

Welcome to The Lake: Your Private Paradise Awaits!

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Lakefront Escape with Gorgeous Views a Short Trip from New York City!, holiday rental in Pawling

Lakefront Escape with Gorgeous Views a Short Trip from New York City!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stylish and modern house in the quaint town of Millbrook., holiday rental in Pawling

Stylish and modern house in the quaint town of Millbrook.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular Short Term Vacation Rental in Kent, holiday rental in Pawling

Spectacular Short Term Vacation Rental in Kent

3 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Peaceful Candlewood  lake/woods retreat., holiday rental in Pawling

Peaceful Candlewood lake/woods retreat.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Exceptional Beauty On The Water!! Candlewood Lake - Danbury, CT, holiday rental in Pawling

Exceptional Beauty On The Water!! Candlewood Lake - Danbury, CT

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Direct Water Front Home, holiday rental in Pawling

Direct Water Front Home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lakefront Luxury Retreat on Candlewood Lake, holiday rental in Pawling

Lakefront Luxury Retreat on Candlewood Lake

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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1905 Remodeled New England Cape Quintessential Connecticut Countryside Getaway, holiday rental in Pawling

1905 Remodeled New England Cape Quintessential Connecticut Countryside Getaway

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Lookout on Candlewood Lake, holiday rental in Pawling

The Lookout on Candlewood Lake

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Modern cottage on the Housatonic River, holiday rental in Pawling

Modern cottage on the Housatonic River

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Gorgeous Lake Adjacent Home - Pet Friendly and Fenced!, holiday rental in Pawling

Gorgeous Lake Adjacent Home - Pet Friendly and Fenced!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront home with private dock, kayaks,  and paddleboard.  Boat rentals nearby, holiday rental in Pawling

Lakefront home with private dock, kayaks, and paddleboard. Boat rentals nearby

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Level, direct lakefront, expansive western views, beach on Candlewood Lake, holiday rental in Pawling

Level, direct lakefront, expansive western views, beach on Candlewood Lake

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Direct Waterfront on Candlewood Lake with/ boat slip & expansive outdoor kitchen, holiday rental in Pawling

Direct Waterfront on Candlewood Lake with/ boat slip & expansive outdoor kitchen

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Waterfront Lake House with Amazing Views, holiday rental in Pawling

Stunning Waterfront Lake House with Amazing Views

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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The Hilltop - Stunning, holiday rental in Pawling

The Hilltop - Stunning

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private Kent Getaway With Views, Pond & Pool, holiday rental in Pawling

Private Kent Getaway With Views, Pond & Pool

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Immaculate 1780 Millbrook Classic, holiday rental in Pawling

Immaculate 1780 Millbrook Classic

5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful mountaintop getaway for peace and quiet, holiday rental in Pawling

Beautiful mountaintop getaway for peace and quiet

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3 BR Cabin in Private Candlewood Lake Community, holiday rental in Pawling

3 BR Cabin in Private Candlewood Lake Community

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Rustic Country Beach Cottage Candlewood Lake, holiday rental in Pawling

Rustic Country Beach Cottage Candlewood Lake

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stately 1792 retreat on 23 acres, chic modern renovation with gunite pool, holiday rental in Pawling

Stately 1792 retreat on 23 acres, chic modern renovation with gunite pool

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Charming country home in Roxbury, holiday rental in Pawling

Charming country home in Roxbury

3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Mabels Hollow Farm, En suite bedroom farm stay,, holiday rental in Pawling

Mabels Hollow Farm, En suite bedroom farm stay,

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Stunning Lakefront Home w/ Private Dock for Swimming (and Kayaks For Use)., holiday rental in Pawling

Stunning Lakefront Home w/ Private Dock for Swimming (and Kayaks For Use).

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Millbrook Country Dream! Tennis/Swim/Play, holiday rental in Pawling

Millbrook Country Dream! Tennis/Swim/Play

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Lake House Rental On Your Own Private Lake, holiday rental in Pawling

Lake House Rental On Your Own Private Lake

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Kent Victorian Room 1, holiday rental in Pawling

Kent Victorian Room 1

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Kent Victorian Room 4, holiday rental in Pawling

Kent Victorian Room 4

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Kent Victorian Room 5, holiday rental in Pawling

Kent Victorian Room 5

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Kent Victorian Room 3, holiday rental in Pawling

Kent Victorian Room 3

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Kent Victorian Room 2, holiday rental in Pawling

Kent Victorian Room 2

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sherman Home w/Lakefront Deck & Swimming Dock, holiday rental in Pawling

Sherman Home w/Lakefront Deck & Swimming Dock

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Tentrr - Cooke's Creek, holiday rental in Pawling

Tentrr - Cooke's Creek

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Holmestead Woods, holiday rental in Pawling

Tentrr Signature Site - Holmestead Woods

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Lake Summer Home with a Dog (Monthly rental only), holiday rental in Pawling

Lake Summer Home with a Dog (Monthly rental only)

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Country Condo ( 3 Months mimimun ), holiday rental in Pawling

Country Condo ( 3 Months mimimun )

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Private Getaway <2 Mi to Croton Falls Station, holiday rental in Pawling

NEW! Private Getaway <2 Mi to Croton Falls Station

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Midcentury Modern House with Stunning Views, holiday rental in Pawling

Midcentury Modern House with Stunning Views

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Family Getaway w/ Fireplace in Sherman on 4 Acres!, holiday rental in Pawling

Family Getaway w/ Fireplace in Sherman on 4 Acres!

7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Sunset Manor, holiday rental in Pawling

Sunset Manor

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Newly Listed Lake House! Private Beach on Candlewood Lake, New Construction Beau, holiday rental in Pawling

Newly Listed Lake House! Private Beach on Candlewood Lake, New Construction Beau

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Modern NY Home w/ Views By Hudson Valley Hiking!, holiday rental in Pawling

Modern NY Home w/ Views By Hudson Valley Hiking!

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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NEW! Chic & Spacious Riverfront Reprieve w/ Dock!, holiday rental in Pawling

NEW! Chic & Spacious Riverfront Reprieve w/ Dock!

6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Tentrr Signature Site - Maybrook Farm - The Ridge, holiday rental in Pawling

Tentrr Signature Site - Maybrook Farm - The Ridge

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Night Light Lake House, holiday rental in Pawling

Night Light Lake House

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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