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Wingdale Holiday Rentals

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Lake House Rental On Your Own Private Lake

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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1870s secluded Farmhouse on 10 acres 75 minutes to NYC or Metro North

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Log Cabin On A Lake With Private Dock

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Quiet Lakefront Retreat only 80 minutes from NYC- with Private Dock

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful contemporary house in Kent, CT, built in 2018.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Lakefront Escape with Gorgeous Views a Short Trip from New York City!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stylish and modern house in the quaint town of Millbrook.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular Short Term Vacation Rental in Kent

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Lake Home with Hot Tub, Pool Table, Ping Pong Table, Fishing, Boats, Fire Pit

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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House on Appalachian Trail, walking distance from NYC trains. 3bd/1ba, 3 acres

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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In town, walk to everything, close to Kent, South Kent and Marvelwood schools

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful Cottage and Waterfront Access

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Renovated, one level home in an excellent location. Walk to the beach!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Direct Water Front Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Country House

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sherman Home w/Lakefront Deck & Swimming Dock

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Log Home - Great Escape for the Holidays! Strong WIFI!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Modern cottage on the Housatonic River

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Direct Waterfront Cottage On Candlewood Lake - Sleeps 6

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Serene, Peaceful Get-Away (Log Cabin by the Lake)

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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THE WATERFALL HOUSE!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Secluded country cabin upstate New York, near metro north train

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Country Studio in private setting

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Family Getaway w/ Fireplace in Sherman on 4 Acres!

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Private Kent Getaway With Views, Pond & Pool

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful, All-Season, Rustic Family Getaway

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Modern Barn, NEW Luxurious Home

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Exclusive & Bucolic Spot in Ideal Area with Heated & Private Pool

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Hilltop - Stunning

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful mountaintop getaway for peace and quiet

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Immaculate 1780 Millbrook Classic

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Apartment in scenic Hudson Valley New York

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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New Listing-Best Location on Candlewood Lakefront Home -1 Acre w/ Dock

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Rustic Country Beach Cottage Candlewood Lake

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Mabels Hollow Farm, En suite bedroom farm stay,

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Millbrook Country Dream! Tennis/Swim/Play

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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STEPPING STONES, Candlewood Lake Cottage, 3BR 2BA w/ Hot Tub & Pool Table!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Still Waters Retreat

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Red Door Country Retreat

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Beautiful Lake House On Peaceful Whaley Lake

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful lake view home on Whaley Lake in Holmes, NY.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Mabels Hollow Farm, In the heart of Litchfield County

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 6
Match: Sleeps
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Stay on an Alpaca Farm

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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NEW LISTING! Waterfront Paradise on Candlewood Lake

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Summer Cottage - Bike to Lake Waramaug

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Maybrook Farm - The Ridge

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Night Light Lake House

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Horse Farm

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Tranquil, Private, Luxury Retreat

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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