Vacation rentals in Wingdale, NY

47 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Wingdale, NY

Trailside Base w/ Gazebo & Kayaks - Wingdale, NY

Trailside Base w/ Gazebo & Kayaks

Apartment, Wingdale

Trailside Base w/ Gazebo & Kayaks is a apartment in Wingdale, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Trailside Base w/ Gazebo & Kayaks

Trailside Base w/ Gazebo & Kayaks 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: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,848.

From$207/night
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Station Inn Pawling - Wingdale, NY

Station Inn Pawling

Guest House, Wingdale

Station Inn Pawling is a guest house in Wingdale, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family…

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About Station Inn Pawling

Station Inn Pawling is a guest house in Wingdale, with parking. 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,741.

From$220/night
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Artistic barn: wood burning hottub, sauna and pizza oven - Wingdale, NY

Artistic barn: wood burning hottub, sauna and pizza oven

Holiday Home, Wingdale

Artistic barn: wood burning hottub, sauna and pizza oven is a holiday home in Wingdale, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area,…

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About Artistic barn: wood burning hottub, sauna and pizza oven

Artistic barn: wood burning hottub, sauna and pizza oven is a holiday home in Wingdale, with pet-friendly space. 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,110.

From$225/night
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Spacious 4-bedroom estate in adorable Carmel Hamlet with AC - Wingdale, NY

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Holiday Home, Wingdale

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC is a holiday home in Wingdale, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for…

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About Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC 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, pet friendly, pets friendly, gym, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,082.

From$243/night
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Browse 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.

Enjoy pool time at our spacious home; minutes from the village of Millbrook! - Wingdale, NY

Enjoy pool time at our spacious home; minutes from the village of Millbrook!

Holiday Home, Wingdale

Enjoy pool time at our spacious home; minutes from the village of Millbrook! is a holiday home in Wingdale, with pet-friendly space, pool access, and kitchen access. This stay gives…

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About Enjoy pool time at our spacious home; minutes from the village of Millbrook!

Enjoy pool time at our spacious home; minutes from the village of Millbrook! is a holiday home in Wingdale, with pet-friendly space, 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, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,372.

From$570/night
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Charming 2-bedroom villa in serene Holmes with AC, WiFi - Wingdale, NY

Charming 2-bedroom villa in serene Holmes with AC, WiFi

Villa, Wingdale

Charming 2-bedroom villa in serene Holmes with AC, WiFi is a villa in Wingdale, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Charming 2-bedroom villa in serene Holmes with AC, WiFi

Charming 2-bedroom villa in serene Holmes with AC, WiFi is a villa in Wingdale, with 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, ac, air conditioning, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,229.

From$575/night
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Converted Barns, Estate Setting , & Pool in Hudson Valley near Millbrook - Wingdale, NY

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,454.

From$665/night
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Fabulous 4 Season Resort Home on the Ten Mile River - Wingdale, NY

Fabulous 4 Season Resort Home on the Ten Mile River

Holiday Home, Wingdale

Fabulous 4 Season Resort Home on the Ten Mile River is a holiday home in Wingdale, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Fabulous 4 Season Resort Home on the Ten Mile River

Fabulous 4 Season Resort Home on the Ten Mile River 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: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,542.

From$675/night
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Best Wingdale, NY vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village - Wingdale, NY

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Apartment, Wingdale

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village is a apartment in Wingdale, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village is a apartment 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: kitchen, with kitchen, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,944.

From$320/night
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A Peaceful Bucolic Retreat by the Water at the Gateway of Hudson Valley - Wingdale, NY

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,888.

From$321/night
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Waterfront Lake Retreat Dock, Screened Porch, Fully Renovated Designer Interior - Wingdale, NY

Waterfront Lake Retreat Dock, Screened Porch, Fully Renovated Designer Interior

Holiday Home, Wingdale

Waterfront Lake Retreat Dock, Screened Porch, Fully Renovated Designer Interior is a holiday home in Wingdale, with easy beach access, parking, and kitchen access. This stay gives travelers…

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About Waterfront Lake Retreat Dock, Screened Porch, Fully Renovated Designer Interior

Waterfront Lake Retreat Dock, Screened Porch, Fully Renovated Designer Interior is a holiday home in Wingdale, with easy beach access, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,316.

From$460/night
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NYC-Area Escape • Game Room • Firepit • Chef's Kitchen • Near Boarding Schools - Wingdale, NY

NYC-Area Escape • Game Room • Firepit • Chef's Kitchen • Near Boarding Schools

Holiday Home, Wingdale

NYC-Area Escape · Game Room · Firepit · Chef's Kitchen · Near Boarding Schools is a holiday home in Wingdale, with parking and kitchen access. This stay gives travelers a comfortable base…

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About NYC-Area Escape • Game Room • Firepit • Chef's Kitchen • Near Boarding Schools

NYC-Area Escape · Game Room · Firepit · Chef's Kitchen · Near Boarding Schools 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,778.

From$509/night
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Best Pet-Friendly Vacation Rentals in Wingdale, NY

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

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway - Wingdale, NY

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Holiday Home, Wingdale

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway is a holiday home in Wingdale, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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About Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway is a holiday home in Wingdale, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,802.

From$386/night
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YOIN: Whispers of Tranquility, a Zen Retreat - Wingdale, NY

YOIN: Whispers of Tranquility, a Zen Retreat

Holiday Home, Wingdale

YOIN: Whispers of Tranquility, a Zen Retreat is a holiday home in Wingdale, with pet-friendly space and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About YOIN: Whispers of Tranquility, a Zen Retreat

YOIN: Whispers of Tranquility, a Zen Retreat is a holiday home in Wingdale, with pet-friendly space 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, pet friendly, pets friendly, gym, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,073.

From$427/night
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Direct Water Front Home, Private Boat Dock, Kayaks - Wingdale, NY

Direct Water Front Home, Private Boat Dock, Kayaks

Holiday Home, Wingdale

Direct Water Front Home, Private Boat Dock, Kayaks is a holiday home in Wingdale, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Direct Water Front Home, Private Boat Dock, Kayaks

Direct Water Front Home, Private Boat Dock, Kayaks 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,465.

From$724/night
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Enchanting Lake front chalet with backyard and fire pit. Dog friendly. - Wingdale, NY

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,864.

From$325/night
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Best Wingdale, NY vacation rentals with a kitchen

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

Incredible spacious family friendly getaway - Wingdale, NY

Incredible spacious family friendly getaway

Holiday Home, Wingdale

Incredible spacious family friendly getaway is a holiday home in Wingdale, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Incredible spacious family friendly getaway

Incredible spacious family friendly getaway is a holiday home in Wingdale, with 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,257.

From$433/night
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Beautiful Lake View House Overlooking Peaceful Whaley Lake - Wingdale, NY

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,035.

From$518/night
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Beautiful lake view home on Whaley Lake in Holmes, NY. - Wingdale, NY

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, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,080.

From$530/night
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Quintessential Connecticut Living 5BRD/3 bath Home with Game Room and Fire Pit - Wingdale, NY

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

Holiday Home, Wingdale

Quintessential Connecticut Living 5BRD/3 bath Home with Game Room and Fire Pit is a holiday home in Wingdale, with kitchen access and room for a group. This stay gives travelers a…

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

Quintessential Connecticut Living 5BRD/3 bath Home with Game Room and Fire Pit is a holiday home in Wingdale, with 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 gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,987.

From$647/night
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Our Favorite Family-Friendly Vacation Rentals in Wingdale, NY

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

Dainty New Preston Cottage w/ Dock & Lake Views! - Wingdale, NY

Dainty New Preston Cottage w/ Dock & Lake Views!

Holiday Home, Wingdale

Dainty New Preston Cottage w/ Dock & Lake Views! is a holiday home in Wingdale, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Dainty New Preston Cottage w/ Dock & Lake Views!

Dainty New Preston Cottage w/ Dock & Lake Views! is a holiday home in Wingdale, with pet-friendly space and parking. 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 parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,727.

From$283/night
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Dainty New Preston Cottage w/ Dock & Lake Views! - Wingdale, NY

Dainty New Preston Cottage w/ Dock & Lake Views!

Cottage, Wingdale

Dainty New Preston Cottage w/ Dock & Lake Views! is a cottage in Wingdale, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Dainty New Preston Cottage w/ Dock & Lake Views!

Dainty New Preston Cottage w/ Dock & Lake Views! is a cottage 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,831.

From$322/night
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One of the Original Summer Cottages on Lake Warmaug - Wingdale, NY

One of the Original Summer Cottages on Lake Warmaug

Holiday Home, Wingdale

One of the Original Summer Cottages on Lake Warmaug is a holiday home in Wingdale, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About One of the Original Summer Cottages on Lake Warmaug

One of the Original Summer Cottages on Lake Warmaug 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,911.

From$350/night
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Millbrook Cottage Originally a 1927 Sears Kit House - Wingdale, NY

Millbrook Cottage Originally a 1927 Sears Kit House

Cottage, Wingdale

Millbrook Cottage Originally a 1927 Sears Kit House is a cottage in Wingdale. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Millbrook Cottage Originally a 1927 Sears Kit House

Millbrook Cottage Originally a 1927 Sears Kit House is a cottage in Wingdale. 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, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,599.

From$380/night
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