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Holiday Rentals in Wingdale

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5 km
47 rentals in Wingdale.
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!, holiday rental in Wingdale
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!, holiday rental in Wingdale
Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!, holiday rental in Wingdale

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Adorable 3BR-cape near skiing and sledding, holiday rental in Wingdale
Adorable 3BR-cape near skiing and sledding, holiday rental in Wingdale
Adorable 3BR-cape near skiing and sledding, holiday rental in Wingdale

Adorable 3BR-cape near skiing and sledding

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Country House, holiday rental in Wingdale
Country House, holiday rental in Wingdale
Country House, holiday rental in Wingdale

Country House

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautifully restored 1822 Farmhouse, as seen in Better Homes & Gardens Magazine, holiday rental in Wingdale
Beautifully restored 1822 Farmhouse, as seen in Better Homes & Gardens Magazine, holiday rental in Wingdale
Beautifully restored 1822 Farmhouse, as seen in Better Homes & Gardens Magazine, holiday rental in Wingdale

Beautifully restored 1822 Farmhouse, as seen in Better Homes & Gardens Magazine

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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The following properties within 32 kms of Wingdale match all your filters:
Charming Cottage with Fireplace, Great Kitchen & Pool on Private 5 Acres, holiday rental in Wingdale
Charming Cottage with Fireplace, Great Kitchen & Pool on Private 5 Acres, holiday rental in Wingdale
Charming Cottage with Fireplace, Great Kitchen & Pool on Private 5 Acres, holiday rental in Wingdale

Charming Cottage with Fireplace, Great Kitchen & Pool on Private 5 Acres

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Candlewood Lake! Private Pool! Bring your boat!, holiday rental in Wingdale
Candlewood Lake! Private Pool! Bring your boat!, holiday rental in Wingdale
Candlewood Lake! Private Pool! Bring your boat!, holiday rental in Wingdale

Candlewood Lake! Private Pool! Bring your boat!

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 10
Match: Sleeps
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Glamping, family fun, pet friendly, holiday rental in Wingdale
Glamping, family fun, pet friendly, holiday rental in Wingdale
Glamping, family fun, pet friendly, holiday rental in Wingdale

Glamping, family fun, pet friendly

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly, holiday rental in Wingdale
Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly, holiday rental in Wingdale
Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly, holiday rental in Wingdale

Campers Paradise, cozy tents, hot tub, free EV charger. Pet friendly

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Rare, peaceful glamping, hot shower, mini golf near appalachian trail, holiday rental in Wingdale
Rare, peaceful glamping, hot shower, mini golf near appalachian trail, holiday rental in Wingdale
Rare, peaceful glamping, hot shower, mini golf near appalachian trail, holiday rental in Wingdale

Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Club Getaway Pine Grove 3, holiday rental in Wingdale
Club Getaway Pine Grove 3, holiday rental in Wingdale
Club Getaway Pine Grove 3, holiday rental in Wingdale

Club Getaway Pine Grove 3

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Club Getaway Pine Grove 2, holiday rental in Wingdale
Club Getaway Pine Grove 2, holiday rental in Wingdale
Club Getaway Pine Grove 2, holiday rental in Wingdale

Club Getaway Pine Grove 2

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Club Getaway Valley View 2, holiday rental in Wingdale
Club Getaway Valley View 2, holiday rental in Wingdale
Club Getaway Valley View 2, holiday rental in Wingdale

Club Getaway Valley View 2

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Club Getaway Lake View 2, holiday rental in Wingdale
Club Getaway Lake View 2, holiday rental in Wingdale
Club Getaway Lake View 2, holiday rental in Wingdale

Club Getaway Lake View 2

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Victorian Guest Suite in heart of the Village, holiday rental in Wingdale
Victorian Guest Suite in heart of the Village, holiday rental in Wingdale
Victorian Guest Suite in heart of the Village, holiday rental in Wingdale

Victorian Guest Suite in heart of the Village

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Club Getaway Valley View 3, holiday rental in Wingdale
Club Getaway Valley View 3, holiday rental in Wingdale
Club Getaway Valley View 3, holiday rental in Wingdale

Club Getaway Valley View 3

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Club Getaway Lake View 3, holiday rental in Wingdale
Club Getaway Lake View 3, holiday rental in Wingdale
Club Getaway Lake View 3, holiday rental in Wingdale

Club Getaway Lake View 3

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Club Getaway Mountain View 2, holiday rental in Wingdale
Club Getaway Mountain View 2, holiday rental in Wingdale
Club Getaway Mountain View 2, holiday rental in Wingdale

Club Getaway Mountain View 2

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Club Getaway Mountain View 3, holiday rental in Wingdale
Club Getaway Mountain View 3, holiday rental in Wingdale
Club Getaway Mountain View 3, holiday rental in Wingdale

Club Getaway Mountain View 3

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Club Getaway Mountain View 1, holiday rental in Wingdale
Club Getaway Mountain View 1, holiday rental in Wingdale
Club Getaway Mountain View 1, holiday rental in Wingdale

Club Getaway Mountain View 1

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Club Getaway Valley View 1, holiday rental in Wingdale
Club Getaway Valley View 1, holiday rental in Wingdale
Club Getaway Valley View 1, holiday rental in Wingdale

Club Getaway Valley View 1

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Relaxing summer getaway with sunset views near lake, holiday rental in Wingdale
Relaxing summer getaway with sunset views near lake, holiday rental in Wingdale
Relaxing summer getaway with sunset views near lake, holiday rental in Wingdale

Relaxing summer getaway with sunset views near lake

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy Lakeside Home w/Private Beach, holiday rental in Wingdale
Cozy Lakeside Home w/Private Beach, holiday rental in Wingdale
Cozy Lakeside Home w/Private Beach, holiday rental in Wingdale

Cozy Lakeside Home w/Private Beach

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful mountaintop getaway for peace and quiet, holiday rental in Wingdale
Beautiful mountaintop getaway for peace and quiet, holiday rental in Wingdale
Beautiful mountaintop getaway for peace and quiet, holiday rental in Wingdale

Beautiful mountaintop getaway for peace and quiet

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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In town, walk to everything, close to Kent, South Kent and Marvelwood schools, holiday rental in Wingdale
In town, walk to everything, close to Kent, South Kent and Marvelwood schools, holiday rental in Wingdale
In town, walk to everything, close to Kent, South Kent and Marvelwood schools, holiday rental in Wingdale

In town, walk to everything, close to Kent, South Kent and Marvelwood schools

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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), holiday rental in Wingdale
Serene, Peaceful Get-Away (Log Cabin by the Lake), holiday rental in Wingdale

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Club Getaway Pine Grove 1, holiday rental in Wingdale
Club Getaway Pine Grove 1, holiday rental in Wingdale
Club Getaway Pine Grove 1, holiday rental in Wingdale

Club Getaway Pine Grove 1

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stay on an Alpaca Farm, holiday rental in Wingdale
Stay on an Alpaca Farm, holiday rental in Wingdale
Stay on an Alpaca Farm, holiday rental in Wingdale

Stay on an Alpaca Farm

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront House and Artist's Studio in the Woods, holiday rental in Wingdale
Waterfront House and Artist's Studio in the Woods, holiday rental in Wingdale
Waterfront House and Artist's Studio in the Woods, holiday rental in Wingdale

Waterfront House and Artist's Studio in the Woods

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Beekman Salt Box -- Historic Hudson Valley Home, holiday rental in Wingdale
The Beekman Salt Box -- Historic Hudson Valley Home, holiday rental in Wingdale
The Beekman Salt Box -- Historic Hudson Valley Home, holiday rental in Wingdale

The Beekman Salt Box -- Historic Hudson Valley Home

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Fabulous 4 Season Resort Home  on the Ten Mile River, holiday rental in Wingdale
Fabulous 4 Season Resort Home  on the Ten Mile River, holiday rental in Wingdale
Fabulous 4 Season Resort Home  on the Ten Mile River, holiday rental in Wingdale

Fabulous 4 Season Resort Home on the Ten Mile River

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Artistic concered barn, holiday rental in Wingdale
Artistic concered barn, holiday rental in Wingdale
Artistic concered barn, holiday rental in Wingdale

Artistic concered barn

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Near Lake Waramaug & Candlewood Lakes, holiday rental in Wingdale
Near Lake Waramaug & Candlewood Lakes, holiday rental in Wingdale
Near Lake Waramaug & Candlewood Lakes, holiday rental in Wingdale

Near Lake Waramaug & Candlewood Lakes

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub, holiday rental in Wingdale
Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub, holiday rental in Wingdale
Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub, holiday rental in Wingdale

Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful lake view home on Whaley Lake in Holmes, NY., holiday rental in Wingdale
Beautiful lake view home on Whaley Lake in Holmes, NY., holiday rental in Wingdale
Beautiful lake view home on Whaley Lake in Holmes, NY., holiday rental in Wingdale

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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Beautiful Horse Farm, holiday rental in Wingdale
Beautiful Horse Farm, holiday rental in Wingdale
Beautiful Horse Farm, holiday rental in Wingdale

Beautiful Horse Farm

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Lake View House Overlooking Peaceful Whaley Lake, holiday rental in Wingdale
Beautiful Lake View House Overlooking Peaceful Whaley Lake, holiday rental in Wingdale
Beautiful Lake View House Overlooking Peaceful Whaley Lake, holiday rental in Wingdale

Beautiful Lake View House Overlooking Peaceful Whaley Lake

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Quintessential Connecticut Living 5BRD/3 bath Home with Game Room and Fire Pit, holiday rental in Wingdale
Quintessential Connecticut Living 5BRD/3 bath Home with Game Room and Fire Pit, holiday rental in Wingdale
Quintessential Connecticut Living 5BRD/3 bath Home with Game Room and Fire Pit, holiday rental in Wingdale

Quintessential Connecticut Living 5BRD/3 bath Home with Game Room and Fire Pit

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Millbrook - Beautifully Restored 1840 Colonial - Dutchess Co. NY, holiday rental in Wingdale
Millbrook - Beautifully Restored 1840 Colonial - Dutchess Co. NY, holiday rental in Wingdale
Millbrook - Beautifully Restored 1840 Colonial - Dutchess Co. NY, holiday rental in Wingdale

Millbrook - Beautifully Restored 1840 Colonial - Dutchess Co. NY

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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COMPLIMENTARY BREAKFAST- 1 per week…AUTUMN IS GORGEOUS IN THE HUDSON VALLEY!!, holiday rental in Wingdale
COMPLIMENTARY BREAKFAST- 1 per week…AUTUMN IS GORGEOUS IN THE HUDSON VALLEY!!, holiday rental in Wingdale
COMPLIMENTARY BREAKFAST- 1 per week…AUTUMN IS GORGEOUS IN THE HUDSON VALLEY!!, holiday rental in Wingdale

COMPLIMENTARY BREAKFAST- 1 per week…AUTUMN IS GORGEOUS IN THE HUDSON VALLEY!!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC, holiday rental in Wingdale
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC, holiday rental in Wingdale
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC, holiday rental in Wingdale

Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Nature lover's cabin on over 60 acres., holiday rental in Wingdale
Nature lover's cabin on over 60 acres., holiday rental in Wingdale
Nature lover's cabin on over 60 acres., holiday rental in Wingdale

Nature lover's cabin on over 60 acres.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Cozy lake house retreat!, holiday rental in Wingdale
Cozy lake house retreat!, holiday rental in Wingdale
Cozy lake house retreat!, holiday rental in Wingdale

Cozy lake house retreat!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful and private modernist 3 bedroom home with gunite pool on 6 acres., holiday rental in Wingdale
Beautiful and private modernist 3 bedroom home with gunite pool on 6 acres., holiday rental in Wingdale
Beautiful and private modernist 3 bedroom home with gunite pool on 6 acres., holiday rental in Wingdale

Beautiful and private modernist 3 bedroom home with gunite pool on 6 acres.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Quiet Historic Retreat, holiday rental in Wingdale
Quiet Historic Retreat, holiday rental in Wingdale
Quiet Historic Retreat, holiday rental in Wingdale

Quiet Historic Retreat

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A-Frame Getaway with Pool, holiday rental in Wingdale
A-Frame Getaway with Pool, holiday rental in Wingdale
A-Frame Getaway with Pool, holiday rental in Wingdale

A-Frame Getaway with Pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Perfection in Litchfield County, holiday rental in Wingdale
Perfection in Litchfield County, holiday rental in Wingdale
Perfection in Litchfield County, holiday rental in Wingdale

Perfection in Litchfield County

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Creek Side Cabin with Wood Fired Hot Tub and Fire Pit, holiday rental in Wingdale
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit, holiday rental in Wingdale
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit, holiday rental in Wingdale

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Showing results 1-47 of 47
Frequently Asked Questions about Wingdale