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Holiday Homes in Wingdale

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50 rentals in Wingdale.
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Welcome to The Lake: Your Private Paradise Awaits!, holiday rental in Wingdale

Welcome to The Lake: Your Private Paradise Awaits!

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Lake House Rental On Your Own Private Lake, holiday rental in Wingdale

Lake House Rental On Your Own Private Lake

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six., holiday rental in Wingdale

Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lakefront Escape with Gorgeous Views a Short Trip from New York City!, holiday rental in Wingdale

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

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

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 Wingdale

Peaceful Candlewood lake/woods retreat.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stylish and modern house in the quaint town of Millbrook., holiday rental in Wingdale

Stylish and modern house in the quaint town of Millbrook.

3 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 Wingdale

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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Historic Warren/Kent Home, holiday rental in Wingdale

Historic Warren/Kent Home

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Private Annex/Former Artist Studo, holiday rental in Wingdale

Private Annex/Former Artist Studo

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Direct Water Front Home, holiday rental in Wingdale

Direct Water Front Home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gorgeous Lake Adjacent Home - Pet Friendly and Fenced!, holiday rental in Wingdale

Gorgeous Lake Adjacent Home - Pet Friendly and Fenced!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront Luxury Retreat on Candlewood Lake, holiday rental in Wingdale

Lakefront Luxury Retreat on Candlewood Lake

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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The Lookout on Candlewood Lake, holiday rental in Wingdale

The Lookout on Candlewood Lake

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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TREEMENDOUS VIEWS COTTAGE, holiday rental in Wingdale

TREEMENDOUS VIEWS COTTAGE

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Modern cottage on the Housatonic River, holiday rental in Wingdale

Modern cottage on the Housatonic River

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Level, direct lakefront, expansive western views, beach on Candlewood Lake, holiday rental in Wingdale

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

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Warren country retreat, holiday rental in Wingdale

Warren country retreat

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Secluded country cabin upstate New York, near  metro north train, holiday rental in Wingdale

Secluded country cabin upstate New York, near metro north train

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Waterfront House on Lake Waramaug!, holiday rental in Wingdale

Waterfront House on Lake Waramaug!

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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The Hilltop - Stunning, holiday rental in Wingdale

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 Wingdale

Private Kent Getaway With Views, Pond & Pool

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Direct Waterfront on Candlewood Lake with/ boat slip & expansive outdoor kitchen, holiday rental in Wingdale

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

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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SUN HILL FARM 1/4 MILE FROM LAKE WARAMAU, holiday rental in Wingdale

SUN HILL FARM 1/4 MILE FROM LAKE WARAMAU

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Immaculate 1780 Millbrook Classic, holiday rental in Wingdale

Immaculate 1780 Millbrook Classic

5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Serene, Peaceful Get-Away (Log Cabin by the Lake), holiday rental in Wingdale

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

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

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 Wingdale

Rustic Country Beach Cottage Candlewood Lake

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

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 Wingdale

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 Wingdale

Millbrook Country Dream! Tennis/Swim/Play

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

Beautiful mountaintop getaway for peace and quiet

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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100% WASHINGTON PoshPadsCT 'SOUTH ST' Mint 4 BR, Heated Pool, BBQ, Bikes, holiday rental in Wingdale

100% WASHINGTON PoshPadsCT 'SOUTH ST' Mint 4 BR, Heated Pool, BBQ, Bikes

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Exclusive Rental in Beautiful Amenia!, holiday rental in Wingdale

Exclusive Rental in Beautiful Amenia!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Dainty New Preston Cottage w/ Dock & Lake Views!, holiday rental in Wingdale

Dainty New Preston Cottage w/ Dock & Lake Views!

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Kent Victorian Room 1, holiday rental in Wingdale

Kent Victorian Room 1

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

Kent Victorian Room 4

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

Kent Victorian Room 5

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

Kent Victorian Room 3

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

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 Wingdale

Sherman Home w/Lakefront Deck & Swimming Dock

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lake Summer Home with a Dog (Monthly rental only), holiday rental in Wingdale

Lake Summer Home with a Dog (Monthly rental only)

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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New Listing!  Stunning Country Home 90 Minutes from NYC, holiday rental in Wingdale

New Listing! Stunning Country Home 90 Minutes from NYC

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Gorgeous 5 Bedroom Waterfront Property on Candlewood Lake (30+ day rental), holiday rental in Wingdale

Gorgeous 5 Bedroom Waterfront Property on Candlewood Lake (30+ day rental)

5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
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Charming country home in Roxbury, holiday rental in Wingdale

Charming country home in Roxbury

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

Family Getaway w/ Fireplace in Sherman on 4 Acres!

7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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NEW! Historic Sherman Home on Valley Pond w/ Pool!, holiday rental in Wingdale

NEW! Historic Sherman Home on Valley Pond w/ Pool!

7 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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NEWLY LISTED! Walk to Private Beach on Candlewood Lake, New Construction with Be, holiday rental in Wingdale

NEWLY LISTED! Walk to Private Beach on Candlewood Lake, New Construction with Be

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

NEW! Chic & Spacious Riverfront Reprieve w/ Dock!

6 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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The Lakeside Nook, holiday rental in Wingdale

The Lakeside Nook

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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