Vacation rentals in Middlebury, CT

70 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Middlebury, CT

1950s Charm In The Heart Of Waterbury - Middlebury, CT

1950s Charm In The Heart Of Waterbury

Homestay, Middlebury

1950s Charm In The Heart Of Waterbury is a homestay in Middlebury, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About 1950s Charm In The Heart Of Waterbury

1950s Charm In The Heart Of Waterbury is a homestay in Middlebury, 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, paid parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $426.

From$47/night
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1950s Charm In The Heart Of Waterbury - Middlebury, CT

1950s Charm In The Heart Of Waterbury

Homestay, Middlebury

1950s Charm In The Heart Of Waterbury is a homestay in Middlebury, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About 1950s Charm In The Heart Of Waterbury

1950s Charm In The Heart Of Waterbury is a homestay in Middlebury, 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 $426.

From$47/night
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Town Plot Waterbury - Middlebury, CT

Town Plot Waterbury

Homestay, Middlebury

Town Plot Waterbury is a homestay in Middlebury, 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 Town Plot Waterbury

Town Plot Waterbury is a homestay in Middlebury, 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 paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $426.

From$47/night
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Town Plot Waterbury - Middlebury, CT

Town Plot Waterbury

Homestay, Middlebury

Town Plot Waterbury is a homestay in Middlebury, 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 Town Plot Waterbury

Town Plot Waterbury is a homestay in Middlebury, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $426.

From$47/night
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Browse Vacation Rentals with a Pool in Middlebury, CT

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

Spacious Woodbury Home w/ Pool + Hot Tub! - Middlebury, CT

Spacious Woodbury Home w/ Pool + Hot Tub!

Holiday Home, Middlebury

Spacious Woodbury Home w/ Pool + Hot Tub! is a holiday home in Middlebury, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Spacious Woodbury Home w/ Pool + Hot Tub!

Spacious Woodbury Home w/ Pool + Hot Tub! is a holiday home in Middlebury, 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 $5,738.

From$571/night
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Charming 3-bedroom house with WiFi, AC, salt water pool, 35-mins from Mohawk Ski - Middlebury, CT

Charming 3-bedroom house with WiFi, AC, salt water pool, 35-mins from Mohawk Ski

Holiday Home, Middlebury

Charming 3-bedroom house with WiFi, AC, salt water pool, 35-mins from Mohawk Ski is a holiday home in Middlebury, with pool access, kitchen access, and room for a group. This stay gives…

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About Charming 3-bedroom house with WiFi, AC, salt water pool, 35-mins from Mohawk Ski

Charming 3-bedroom house with WiFi, AC, salt water pool, 35-mins from Mohawk Ski is a holiday home in Middlebury, with pool access, 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,612.

From$609/night
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Spacious Woodbury Home w/ Pool + Hot Tub! - Middlebury, CT

Spacious Woodbury Home w/ Pool + Hot Tub!

Holiday Home, Middlebury

Spacious Woodbury Home w/ Pool + Hot Tub! is a holiday home in Middlebury, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Spacious Woodbury Home w/ Pool + Hot Tub!

Spacious Woodbury Home w/ Pool + Hot Tub! is a holiday home in Middlebury, with 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, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,155.

From$682/night
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Spacious Woodbury Home w/ Pool + Hot Tub! - Middlebury, CT

Spacious Woodbury Home w/ Pool + Hot Tub!

Cottage, Middlebury

Spacious Woodbury Home w/ Pool + Hot Tub! is a cottage in Middlebury, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Spacious Woodbury Home w/ Pool + Hot Tub!

Spacious Woodbury Home w/ Pool + Hot Tub! is a cottage in Middlebury, with 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, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,389.

From$736/night
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Best Middlebury, CT vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Stylish, Relaxing & Comfy 3 BDR Home. 2 minutes to Lake Compounce - Middlebury, CT

Stylish, Relaxing & Comfy 3 BDR Home. 2 minutes to Lake Compounce

Holiday Home, Middlebury

Stylish, Relaxing & Comfy 3 BDR Home. 2 minutes to Lake Compounce is a holiday home in Middlebury, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About Stylish, Relaxing & Comfy 3 BDR Home. 2 minutes to Lake Compounce

Stylish, Relaxing & Comfy 3 BDR Home. 2 minutes to Lake Compounce is a holiday home in Middlebury, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,804.

From$184/night
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Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use - Middlebury, CT

Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use

Cottage, Middlebury

Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use is a cottage in Middlebury, with pet-friendly space, easy beach access, and parking. This stay gives travelers a…

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About Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use

Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use is a cottage in Middlebury, with pet-friendly space, easy beach access, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,862.

From$207/night
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Cozy 3-bedroom cabin in Woodbury. With Brook and mountain to enjoy. - Middlebury, CT

Cozy 3-bedroom cabin in Woodbury. With Brook and mountain to enjoy.

Cabin, Middlebury

Cozy 3-bedroom cabin in Woodbury. With Brook and mountain to enjoy. is a cabin in Middlebury, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Cozy 3-bedroom cabin in Woodbury. With Brook and mountain to enjoy.

Cozy 3-bedroom cabin in Woodbury. With Brook and mountain to enjoy. is a cabin in Middlebury, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,171.

From$226/night
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Steele Brook Manor Tranquil get away nestled in Litchfield County. - Middlebury, CT

Steele Brook Manor Tranquil get away nestled in Litchfield County.

Apartment, Middlebury

Steele Brook Manor Tranquil get away nestled in Litchfield County. is a apartment in Middlebury, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Steele Brook Manor Tranquil get away nestled in Litchfield County.

Steele Brook Manor Tranquil get away nestled in Litchfield County. is a apartment in Middlebury, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,438.

From$258/night
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Best Pet-Friendly Vacation Rentals in Middlebury, CT

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

Modern cozy home, pet friendly - Middlebury, CT

Modern cozy home, pet friendly

Holiday Home, Middlebury

Modern cozy home, pet friendly is a holiday home in Middlebury, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Modern cozy home, pet friendly

Modern cozy home, pet friendly is a holiday home in Middlebury, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,082.

From$106/night
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Cozy quite private location that makes you feel like home - Middlebury, CT

Cozy quite private location that makes you feel like home

Apartment, Middlebury

Cozy quite private location that makes you feel like home is a apartment in Middlebury, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy quite private location that makes you feel like home

Cozy quite private location that makes you feel like home is a apartment in Middlebury, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,038.

From$113/night
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Private Apartment in Southbury 101 - Middlebury, CT

Private Apartment in Southbury 101

Apartment, Middlebury

Private Apartment in Southbury 101 is a apartment in Middlebury, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Private Apartment in Southbury 101

Private Apartment in Southbury 101 is a apartment in Middlebury, 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 $1,532.

From$162/night
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Private Apartment in Southbury 101 - Middlebury, CT

Private Apartment in Southbury 101

Apartment, Middlebury

Private Apartment in Southbury 101 is a apartment in Middlebury, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Private Apartment in Southbury 101

Private Apartment in Southbury 101 is a apartment in Middlebury, 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 wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,617.

From$190/night
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Best Middlebury, CT vacation rentals with a kitchen

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

Coming Soon! #32- Sleeps 10! - Middlebury, CT

Coming Soon! #32- Sleeps 10!

Apartment, Middlebury

Coming Soon! #32- Sleeps 10! is a apartment in Middlebury, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Coming Soon! #32- Sleeps 10!

Coming Soon! #32- Sleeps 10! is a apartment in Middlebury, 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 $2,060.

From$211/night
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Upscale Waterbury Retreat w/ Indoor Hot Tub! - Middlebury, CT

Upscale Waterbury Retreat w/ Indoor Hot Tub!

Holiday Home, Middlebury

Upscale Waterbury Retreat w/ Indoor Hot Tub! is a holiday home in Middlebury, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base…

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About Upscale Waterbury Retreat w/ Indoor Hot Tub!

Upscale Waterbury Retreat w/ Indoor Hot Tub! is a holiday home in Middlebury, with pet-friendly space, 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, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,631.

From$242/night
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Upscale Waterbury Retreat w/ Indoor Hot Tub! - Middlebury, CT

Upscale Waterbury Retreat w/ Indoor Hot Tub!

Cottage, Middlebury

Upscale Waterbury Retreat w/ Indoor Hot Tub! is a cottage in Middlebury, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Upscale Waterbury Retreat w/ Indoor Hot Tub!

Upscale Waterbury Retreat w/ Indoor Hot Tub! is a cottage in Middlebury, with pet-friendly space, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,922.

From$328/night
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Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area - Middlebury, CT

Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area

Cabin, Middlebury

Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area is a cabin in Middlebury, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area

Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area is a cabin in Middlebury, 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, kitchen, with kitchen, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,022.

From$335/night
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Our Favorite Family-Friendly Vacation Rentals in Middlebury, CT

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

Sunny/Cozy Home w/ Garage and Deck. Minutes from Everything, Family-friendly - Middlebury, CT

Sunny/Cozy Home w/ Garage and Deck. Minutes from Everything, Family-friendly

Holiday Home, Middlebury

Sunny/Cozy Home w/ Garage and Deck. Minutes from Everything, Family-friendly is a holiday home in Middlebury, with outdoor space, parking, and kitchen access. This stay gives travelers a…

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About Sunny/Cozy Home w/ Garage and Deck. Minutes from Everything, Family-friendly

Sunny/Cozy Home w/ Garage and Deck. Minutes from Everything, Family-friendly is a holiday home in Middlebury, with outdoor 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,217.

From$117/night
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Modern Terryville Cottage w/ Deck & Lake View! - Middlebury, CT

Modern Terryville Cottage w/ Deck & Lake View!

Cottage, Middlebury

Modern Terryville Cottage w/ Deck & Lake View! is a cottage in Middlebury, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Modern Terryville Cottage w/ Deck & Lake View!

Modern Terryville Cottage w/ Deck & Lake View! is a cottage in Middlebury, with outdoor 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,921.

From$173/night
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Pleasant 3-bedroom apartment family friendly with WiFi in Waterbury ct - Middlebury, CT

Pleasant 3-bedroom apartment family friendly with WiFi in Waterbury ct

Apartment, Middlebury

Pleasant 3-bedroom apartment family friendly with WiFi in Waterbury ct is a apartment in Middlebury, with pet-friendly space and room for a group. This stay gives travelers a comfortable…

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About Pleasant 3-bedroom apartment family friendly with WiFi in Waterbury ct

Pleasant 3-bedroom apartment family friendly with WiFi in Waterbury ct is a apartment in Middlebury, 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,830.

From$177/night
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Guest Cottage on Country Estate - Middlebury, CT

Guest Cottage on Country Estate

Cottage, Middlebury

Guest Cottage on Country Estate is a cottage in Middlebury, 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 Guest Cottage on Country Estate

Guest Cottage on Country Estate is a cottage in Middlebury, 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 $2,065.

From$211/night
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