Vacation rentals in Wingdale, NY

Best vacation rentals and Airbnb offers in Wingdale, NY

10 ★ 127 reviews

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

Holiday Home, Wingdale

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing! is a holiday home in Wingdale, with pet-friendly space and room for a group. This stay gives travelers a…

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

Escape to your private lakeside estate! Family & dog friendly, wildlife viewing! is a holiday home in Wingdale, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $5,685.

From$812/night

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10 ★ 54 reviews

Private Annex/Former Artist Studio

Holiday Home, Wingdale

Private Annex/Former Artist Studio is a holiday home in Wingdale, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Private Annex/Former Artist Studio

Private Annex/Former Artist Studio is a holiday home in Wingdale, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,891.

From$270/night

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10 ★ 37 reviews

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Apartment, Wingdale

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake is a apartment in Wingdale, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake

Farmhouse apartment on beautiful grounds. 2 mi. to Candlewood Lake is a apartment in Wingdale, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,281.

From$326/night

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10 ★ 28 reviews

Lake Waramaug Cottage

Cottage, Wingdale

Lake Waramaug Cottage is a cottage in Wingdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Lake Waramaug Cottage

Lake Waramaug Cottage is a cottage in Wingdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,472.

From$210/night

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Family-friendly vacation rentals in Wingdale, NY

Plan a trip with stays that give families more room to spread out.

10 ★ 9 reviews

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

Cottage, Wingdale

Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC is a cottage in Wingdale, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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

Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC is a cottage in Wingdale, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,340.

From$477/night

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10 ★ 1 reviews

Cozy Lake Cottage with Hot Tub, Views, Kayaks

Cottage, Wingdale

Cozy Lake Cottage with Hot Tub, Views, Kayaks is a cottage in Wingdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cozy Lake Cottage with Hot Tub, Views, Kayaks

Cozy Lake Cottage with Hot Tub, Views, Kayaks is a cottage in Wingdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,718.

From$388/night

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10 ★ 1 reviews

Lake View Cottage in Candlewood Lake Community

Holiday Home, Wingdale

Lake View Cottage in Candlewood Lake Community is a holiday home in Wingdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Lake View Cottage in Candlewood Lake Community

Lake View Cottage in Candlewood Lake Community is a holiday home in Wingdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,247.

From$464/night

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Fabulous 2-bedroom Creekside cottage on the historic Collins Estate.

Cottage, Wingdale

Fabulous 2-bedroom Creekside cottage on the historic Collins Estate. is a cottage in Wingdale, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Fabulous 2-bedroom Creekside cottage on the historic Collins Estate.

Fabulous 2-bedroom Creekside cottage on the historic Collins Estate. is a cottage in Wingdale, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,032.

From$290/night

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Pet-friendly vacation rentals in Wingdale, NY

Bring your pet along with stays that welcome four-legged travelers.

10 ★ 8 reviews

Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball

Cabin, Wingdale

Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball is a cabin in Wingdale, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers…

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About Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball

Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball is a cabin in Wingdale, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,728.

From$390/night

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10 ★ 1 reviews

Unique Geodesic Dome Escape in Nature!

Holiday Home, Wingdale

Unique Geodesic Dome Escape in Nature! is a holiday home in Wingdale, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Unique Geodesic Dome Escape in Nature!

Unique Geodesic Dome Escape in Nature! is a holiday home in Wingdale, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,515.

From$359/night

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9.4 ★ 8 reviews

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cabin, Wingdale

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly. is a cabin in Wingdale, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a…

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About Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly. is a cabin in Wingdale, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,040.

From$291/night

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8.8 ★ 5 reviews

Perfect cabin getaway. 5mins from hiking trails & lake Waramaug

Cabin, Wingdale

Perfect cabin getaway. 5mins from hiking trails & lake Waramaug is a cabin in Wingdale, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Perfect cabin getaway. 5mins from hiking trails & lake Waramaug

Perfect cabin getaway. 5mins from hiking trails & lake Waramaug is a cabin in Wingdale, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,181.

From$312/night

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Vacation rentals with a pool in Wingdale, NY

Add a pool to the search when you want an easy place to cool off between outings.

10 ★ 1 reviews

Converted Barns, Estate Setting , & Pool in Hudson Valley near Millbrook

Holiday Home, Wingdale

Converted Barns, Estate Setting , & Pool in Hudson Valley near Millbrook is a holiday home in Wingdale, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About Converted Barns, Estate Setting , & Pool in Hudson Valley near Millbrook

Converted Barns, Estate Setting , & Pool in Hudson Valley near Millbrook is a holiday home in Wingdale, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $5,443.

From$778/night

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9.4 ★ 3 reviews

BEST Town, Restaurants, 1.5 Hrs NYC! PoshPadsCT HEATED SPA-POOL, Bike, Hike, Ski

Holiday Home, Wingdale

BEST Town, Restaurants, 1.5 Hrs NYC! PoshPadsCT HEATED SPA-POOL, Bike, Hike, Ski is a holiday home in Wingdale, with pet-friendly space and pool access. This stay gives travelers a…

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About BEST Town, Restaurants, 1.5 Hrs NYC! PoshPadsCT HEATED SPA-POOL, Bike, Hike, Ski

BEST Town, Restaurants, 1.5 Hrs NYC! PoshPadsCT HEATED SPA-POOL, Bike, Hike, Ski is a holiday home in Wingdale, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $5,698.

From$814/night

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8 ★ 3 reviews

Warren-Washington NYC 2Hrs, 5BR Mint, Heated Pool, Tennis, PoshPadsCT \"MELIUS\"

Holiday Home, Wingdale

Warren-Washington NYC 2Hrs, 5BR Mint, Heated Pool, Tennis, PoshPadsCT \"MELIUS\" is a holiday home in Wingdale, with pet-friendly space, pool access, and room for a group. This stay gives…

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About Warren-Washington NYC 2Hrs, 5BR Mint, Heated Pool, Tennis, PoshPadsCT \"MELIUS\"

Warren-Washington NYC 2Hrs, 5BR Mint, Heated Pool, Tennis, PoshPadsCT \"MELIUS\" is a holiday home in Wingdale, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $5,403.

From$772/night

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ESKape Manor: Great Views, Hot Tub & Fun Amenities

Cabin, Wingdale

ESKape Manor: Great Views, Hot Tub & Fun Amenities is a cabin in Wingdale, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About ESKape Manor: Great Views, Hot Tub & Fun Amenities

ESKape Manor: Great Views, Hot Tub & Fun Amenities is a cabin in Wingdale, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,876.

From$554/night

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Vacation rentals with parking in Wingdale, NY

Find vacation rentals that make arriving by car easier.

10 ★ 7 reviews

A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley

Holiday Home, Wingdale

A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley is a holiday home in Wingdale, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley

A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley is a holiday home in Wingdale, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,717.

From$388/night

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9.4 ★ 6 reviews

3 BR Lake House in Gated Candlewood Lake Community

Holiday Home, Wingdale

3 BR Lake House in Gated Candlewood Lake Community is a holiday home in Wingdale, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About 3 BR Lake House in Gated Candlewood Lake Community

3 BR Lake House in Gated Candlewood Lake Community is a holiday home in Wingdale, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,532.

From$362/night

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8 ★ 1 reviews

Ann Inn - Downtown Milford Apartment

Apartment, Wingdale

Ann Inn - Downtown Milford Apartment is a apartment in Wingdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Ann Inn - Downtown Milford Apartment

Ann Inn - Downtown Milford Apartment is a apartment in Wingdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,171.

From$310/night

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10 ★ 2 reviews

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Chalet, Wingdale

Enchanting Lake front chalet with backyard and fire pit. Dog friendly. is a chalet in Wingdale, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable…

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About Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Enchanting Lake front chalet with backyard and fire pit. Dog friendly. is a chalet in Wingdale, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,672.

From$382/night

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Vacation rentals with a kitchen in Wingdale, NY

Compare stays with kitchen access for longer trips and easier meals.

10 ★ 19 reviews

Beautiful lake view home on Whaley Lake in Holmes, NY.

Holiday Home, Wingdale

Beautiful lake view home on Whaley Lake in Holmes, NY. is a holiday home in Wingdale, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Beautiful lake view home on Whaley Lake in Holmes, NY.

Beautiful lake view home on Whaley Lake in Holmes, NY. is a holiday home in Wingdale, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,339.

From$620/night

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10 ★ 17 reviews

Beautiful Lake View House Overlooking Peaceful Whaley Lake

Holiday Home, Wingdale

Beautiful Lake View House Overlooking Peaceful Whaley Lake is a holiday home in Wingdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Beautiful Lake View House Overlooking Peaceful Whaley Lake

Beautiful Lake View House Overlooking Peaceful Whaley Lake is a holiday home in Wingdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, gym, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,339.

From$620/night

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10 ★ 2 reviews

New Milford Home: 29 Mi to Lime Rock Park!

Holiday Home, Wingdale

New Milford Home: 29 Mi to Lime Rock Park! is a holiday home in Wingdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About New Milford Home: 29 Mi to Lime Rock Park!

New Milford Home: 29 Mi to Lime Rock Park! is a holiday home in Wingdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,056.

From$437/night

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10 ★ 1 reviews

The Little Lake Cabin with hot tub

Cabin, Wingdale

The Little Lake Cabin with hot tub is a cabin in Wingdale, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub is a cabin in Wingdale, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,826.

From$547/night

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