Vacation rentals in Woodbury, CT

71 available vacation rental offers

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Best vacation rentals and Airbnb offers in Woodbury, CT

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

1950s Charm In The Heart Of Waterbury

Homestay, Woodbury

1950s Charm In The Heart Of Waterbury is a homestay in Woodbury, 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 Woodbury, 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 - Woodbury, CT

1950s Charm In The Heart Of Waterbury

Homestay, Woodbury

1950s Charm In The Heart Of Waterbury is a homestay in Woodbury, 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 Woodbury, 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 - Woodbury, CT

Town Plot Waterbury

Homestay, Woodbury

Town Plot Waterbury is a homestay in Woodbury, 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 Woodbury, 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 - Woodbury, CT

Town Plot Waterbury

Homestay, Woodbury

Town Plot Waterbury is a homestay in Woodbury, 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 Woodbury, 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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Vacation rentals with a pool in Woodbury, 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! - Woodbury, CT

Spacious Woodbury Home w/ Pool + Hot Tub!

Holiday Home, Woodbury

Spacious Woodbury Home w/ Pool + Hot Tub! is a holiday home in Woodbury, 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 holiday home in Woodbury, 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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Charming 3-bedroom house with WiFi, AC, salt water pool, 35-mins from Mohawk Ski - Woodbury, CT

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

Holiday Home, Woodbury

Charming 3-bedroom house with WiFi, AC, salt water pool, 35-mins from Mohawk Ski is a holiday home in Woodbury, 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 Woodbury, 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 $4,987.

From$712/night
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Spacious Woodbury Home w/ Pool + Hot Tub! - Woodbury, CT

Spacious Woodbury Home w/ Pool + Hot Tub!

Holiday Home, Woodbury

Spacious Woodbury Home w/ Pool + Hot Tub! is a holiday home in Woodbury, 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 Woodbury, 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 $5,058.

From$723/night
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Spacious Woodbury Home w/ Pool + Hot Tub! - Woodbury, CT

Spacious Woodbury Home w/ Pool + Hot Tub!

Cottage, Woodbury

Spacious Woodbury Home w/ Pool + Hot Tub! is a cottage in Woodbury, 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 Woodbury, 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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Vacation rentals with parking in Woodbury, CT

Find vacation rentals that make arriving by car easier.

Cozy small sized apartment with WiFi in awesome Waterbury. - Woodbury, CT

Cozy small sized apartment with WiFi in awesome Waterbury.

Apartment, Woodbury

Cozy small sized apartment with WiFi in awesome Waterbury. is a apartment in Woodbury, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy small sized apartment with WiFi in awesome Waterbury.

Cozy small sized apartment with WiFi in awesome Waterbury. is a apartment in Woodbury, 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 cancellation, parking, free parking, tv, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $935.

From$134/night
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Barn Apartment Hideaway - Woodbury, CT

Barn Apartment Hideaway

Apartment, Woodbury

Barn Apartment Hideaway is a apartment in Woodbury, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Barn Apartment Hideaway

Barn Apartment Hideaway is a apartment in Woodbury, 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 $1,864.

From$266/night
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Cozy 3-bedroom cabin in Woodbury. With Brook and mountain to enjoy. - Woodbury, CT

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

Cabin, Woodbury

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

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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 Woodbury, 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 $1,967.

From$281/night
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Steele Brook Manor Tranquil get away nestled in Litchfield County. - Woodbury, CT

Steele Brook Manor Tranquil get away nestled in Litchfield County.

Apartment, Woodbury

Steele Brook Manor Tranquil get away nestled in Litchfield County. is a apartment in Woodbury, 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 Woodbury, 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 $2,149.

From$307/night
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Pet-friendly vacation rentals in Woodbury, CT

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

Dainty New Preston Cottage w/ Dock & Lake Views! - Woodbury, CT

Dainty New Preston Cottage w/ Dock & Lake Views!

Holiday Home, Woodbury

Dainty New Preston Cottage w/ Dock & Lake Views! is a holiday home in Woodbury, 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 Woodbury, 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 $2,533.

From$259/night
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Roxbury Cabin Retreat - Woodbury, CT

Roxbury Cabin Retreat

Cabin, Woodbury

Roxbury Cabin Retreat is a cabin in Woodbury, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Roxbury Cabin Retreat

Roxbury Cabin Retreat is a cabin in Woodbury, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,835.

From$405/night
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1850's Storybook Colonial Farmhouse - Four Beds, 2.5 Baths, and Outdoor Patio. - Woodbury, CT

1850's Storybook Colonial Farmhouse - Four Beds, 2.5 Baths, and Outdoor Patio.

Holiday Home, Woodbury

1850's Storybook Colonial Farmhouse - Four Beds, 2.5 Baths, and Outdoor Patio. is a holiday home in Woodbury, with pet-friendly space, outdoor space, and parking. This stay gives travelers…

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About 1850's Storybook Colonial Farmhouse - Four Beds, 2.5 Baths, and Outdoor Patio.

1850's Storybook Colonial Farmhouse - Four Beds, 2.5 Baths, and Outdoor Patio. is a holiday home in Woodbury, with pet-friendly space, outdoor 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,212.

From$887/night
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Blackwoods Old Country Home 5 Bedroom Home by RedAwning - Woodbury, CT

Blackwoods Old Country Home 5 Bedroom Home by RedAwning

Holiday Home, Woodbury

Blackwoods Old Country Home 5 Bedroom Home by RedAwning is a holiday home in Woodbury, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable…

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About Blackwoods Old Country Home 5 Bedroom Home by RedAwning

Blackwoods Old Country Home 5 Bedroom Home by RedAwning is a holiday home in Woodbury, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,246.

From$958/night
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Vacation rentals with a kitchen in Woodbury, CT

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

Excellent Home Away From Home - Woodbury, CT

Excellent Home Away From Home

Holiday Home, Woodbury

Excellent Home Away From Home is a holiday home in Woodbury, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Excellent Home Away From Home

Excellent Home Away From Home is a holiday home in Woodbury, 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: kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,343.

From$192/night
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Modern Terryville Cottage w/ Deck & Lake View! - Woodbury, CT

Modern Terryville Cottage w/ Deck & Lake View!

Cottage, Woodbury

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

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,201.

From$242/night
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Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area - Woodbury, CT

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

Cabin, Woodbury

Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area is a cabin in Woodbury, 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 Woodbury, 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 $2,670.

From$381/night
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Charming country home in Roxbury - Woodbury, CT

Charming country home in Roxbury

Holiday Home, Woodbury

Charming country home in Roxbury is a holiday home in Woodbury, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Charming country home in Roxbury

Charming country home in Roxbury is a holiday home in Woodbury, 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, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,506.

From$501/night
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Family-friendly vacation rentals in Woodbury, 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 - Woodbury, CT

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

Holiday Home, Woodbury

Sunny/Cozy Home w/ Garage and Deck. Minutes from Everything, Family-friendly is a holiday home in Woodbury, 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 Woodbury, 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 $1,072.

From$153/night
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Pleasant 3-bedroom apartment family friendly with WiFi in Waterbury ct - Woodbury, CT

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

Apartment, Woodbury

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

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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 Woodbury, 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 $1,620.

From$231/night
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Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use - Woodbury, CT

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

Cottage, Woodbury

Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use is a cottage in Woodbury, 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 Woodbury, 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 $1,645.

From$235/night
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Modern Terryville Cottage w/ Deck & Lake View! - Woodbury, CT

Modern Terryville Cottage w/ Deck & Lake View!

Cottage, Woodbury

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

Read more

About Modern Terryville Cottage w/ Deck & Lake View!

Modern Terryville Cottage w/ Deck & Lake View! is a cottage in Woodbury, 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 $1,684.

From$241/night
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