Vacation rentals in Stockbridge, MA

120 available vacation rental offers

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Best vacation rentals and Airbnb offers in Stockbridge, MA

Lenox in-law studio - Stockbridge, MA

Lenox in-law studio

Apartment, Stockbridge

Lenox in-law studio is a apartment in Stockbridge, 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 Lenox in-law studio

Lenox in-law studio is a apartment in Stockbridge, 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 $1,293.

From$185/night
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Cozy Stockbridge Cabin - Walk to Beach & Lake! - Stockbridge, MA

Cozy Stockbridge Cabin - Walk to Beach & Lake!

Holiday Home, Stockbridge

Cozy Stockbridge Cabin - Walk to Beach & Lake! is a holiday home in Stockbridge, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy Stockbridge Cabin - Walk to Beach & Lake!

Cozy Stockbridge Cabin - Walk to Beach & Lake! is a holiday home in Stockbridge, with 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, free wifi, parking, paid parking, and non smoking::room.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,020.

From$206/night
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Downtown Gateway to the Berkshires. Walk to Everything. - Stockbridge, MA

Downtown Gateway to the Berkshires. Walk to Everything.

Apartment, Stockbridge

Downtown Gateway to the Berkshires. Walk to Everything. is a apartment in Stockbridge, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Downtown Gateway to the Berkshires. Walk to Everything.

Downtown Gateway to the Berkshires. Walk to Everything. is a apartment in Stockbridge, 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, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,491.

From$213/night
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Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox) - Stockbridge, MA

Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)

Condo, Stockbridge

Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox) is a condo in Stockbridge, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)

Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox) is a condo in Stockbridge, 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 $1,564.

From$223/night
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Vacation rentals with a pool in Stockbridge, MA

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

Peaceful 1BR Condo with Pond View - Stockbridge, MA

Peaceful 1BR Condo with Pond View

Condo, Stockbridge

Peaceful 1BR Condo with Pond View is a condo in Stockbridge, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Peaceful 1BR Condo with Pond View

Peaceful 1BR Condo with Pond View is a condo in Stockbridge, with pool 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,937.

From$277/night
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Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee - Stockbridge, MA

Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee

Apartment, Stockbridge

Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee is a apartment in Stockbridge, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee

Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee is a apartment in Stockbridge, 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,040.

From$291/night
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Tranquil Lakeside Escape in the Berkshires - Stockbridge, MA

Tranquil Lakeside Escape in the Berkshires

Condo, Stockbridge

Tranquil Lakeside Escape in the Berkshires is a condo in Stockbridge, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires is a condo in Stockbridge, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,367.

From$338/night
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Spacious Villa with Access to Various Amenities! - Stockbridge, MA

Spacious Villa with Access to Various Amenities!

Villa, Stockbridge

Spacious Villa with Access to Various Amenities! is a villa in Stockbridge, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Spacious Villa with Access to Various Amenities!

Spacious Villa with Access to Various Amenities! is a villa in Stockbridge, 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 $2,421.

From$346/night
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Vacation rentals with parking in Stockbridge, MA

Find vacation rentals that make arriving by car easier.

The Berkshire Music Loft at Eastview Studio with Piano, Balcony & Mountain View - Stockbridge, MA

The Berkshire Music Loft at Eastview Studio with Piano, Balcony & Mountain View

Apartment, Stockbridge

The Berkshire Music Loft at Eastview Studio with Piano, Balcony & Mountain View is a apartment in Stockbridge, with outdoor space and parking. This stay gives travelers a comfortable base…

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About The Berkshire Music Loft at Eastview Studio with Piano, Balcony & Mountain View

The Berkshire Music Loft at Eastview Studio with Piano, Balcony & Mountain View is a apartment in Stockbridge, with 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,537.

From$220/night
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Shaker Mill Inn - Stockbridge, MA

Shaker Mill Inn

B & B, Stockbridge

Shaker Mill Inn is a b & b in Stockbridge, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Shaker Mill Inn

Shaker Mill Inn is a b & b in Stockbridge, 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 breakfast, parking, free parking, house keeping, and housekeeping.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,949.

From$254/night
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Whistler's Inn - Stockbridge, MA

Whistler's Inn

B & B, Stockbridge

Whistler's Inn is a b & b in Stockbridge, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Whistler's Inn

Whistler's Inn is a b & b in Stockbridge, 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 breakfast, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,279.

From$291/night
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Eastgate Inn B&B - Stockbridge, MA

Eastgate Inn B&B

B & B, Stockbridge

Eastgate Inn B&B is a b & b in Stockbridge, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Eastgate Inn B&B

Eastgate Inn B&B is a b & b in Stockbridge, 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 breakfast, free wifi, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,477.

From$317/night
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Pet-friendly vacation rentals in Stockbridge, MA

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

Cozy 1-bedroom studio in serene Great Barrington with AC - Stockbridge, MA

Cozy 1-bedroom studio in serene Great Barrington with AC

Apartment, Stockbridge

Cozy 1-bedroom studio in serene Great Barrington with AC is a apartment in Stockbridge, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for…

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About Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC is a apartment in Stockbridge, 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, dryer, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $846.

From$121/night
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Whistler's Inn - Stockbridge, MA

Whistler's Inn

B & B, Stockbridge

Whistler's Inn is a b & b in Stockbridge, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Whistler's Inn

Whistler's Inn is a b & b in Stockbridge, 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 breakfast, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,051.

From$262/night
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Shaker Mill Inn - Stockbridge, MA

Shaker Mill Inn

B & B, Stockbridge

Shaker Mill Inn is a b & b in Stockbridge, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

Read more

About Shaker Mill Inn

Shaker Mill Inn is a b & b in Stockbridge, 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 breakfast, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,205.

From$282/night
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Shaker Mill Inn - Stockbridge, MA

Shaker Mill Inn

B & B, Stockbridge

Shaker Mill Inn is a b & b in Stockbridge, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

Read more

About Shaker Mill Inn

Shaker Mill Inn is a b & b in Stockbridge, 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 breakfast, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,205.

From$282/night
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Vacation rentals with a kitchen in Stockbridge, MA

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

Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires - Stockbridge, MA

Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires

Cottage, Stockbridge

Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires is a cottage in Stockbridge, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires

Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires is a cottage in Stockbridge, 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 $1,994.

From$285/night
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The Docent`s House - Honoring a Legacy - Stockbridge, MA

The Docent`s House - Honoring a Legacy

Holiday Home, Stockbridge

The Docent`s House - Honoring a Legacy is a holiday home in Stockbridge, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Docent`s House - Honoring a Legacy

The Docent`s House - Honoring a Legacy is a holiday home in Stockbridge, 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 $2,066.

From$295/night
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Lovely Lakefront Cottage, Peaceful Setting, Hiking And More - Stockbridge, MA

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More

Holiday Home, Stockbridge

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More is a holiday home in Stockbridge, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Lovely Lakefront Cottage, Peaceful Setting, Hiking And More

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More is a holiday home in Stockbridge, 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 $2,163.

From$309/night
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Spacious Comfortable Charming Family Farmhouse Great Location - Stockbridge, MA

Spacious Comfortable Charming Family Farmhouse Great Location

Country House, Stockbridge

Spacious Comfortable Charming Family Farmhouse Great Location is a country house in Stockbridge, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About Spacious Comfortable Charming Family Farmhouse Great Location

Spacious Comfortable Charming Family Farmhouse Great Location is a country house in Stockbridge, 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 wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,737.

From$391/night
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Family-friendly vacation rentals in Stockbridge, MA

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

Berkshire Mountain Cottage: in the Heart of the Berkshires - Stockbridge, MA

Berkshire Mountain Cottage: in the Heart of the Berkshires

Cottage, Stockbridge

Berkshire Mountain Cottage: in the Heart of the Berkshires is a cottage in Stockbridge, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Berkshire Mountain Cottage: in the Heart of the Berkshires

Berkshire Mountain Cottage: in the Heart of the Berkshires is a cottage in Stockbridge, 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 $1,876.

From$268/night
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Romantic Berkshires Cottage - Stunning Views, Pool - Stockbridge, MA

Romantic Berkshires Cottage - Stunning Views, Pool

Cottage, Stockbridge

Romantic Berkshires Cottage - Stunning Views, Pool is a cottage in Stockbridge, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Romantic Berkshires Cottage - Stunning Views, Pool

Romantic Berkshires Cottage - Stunning Views, Pool is a cottage in Stockbridge, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,065.

From$295/night
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Beachwood Cottage - Stockbridge, MA

Beachwood Cottage

Cottage, Stockbridge

Beachwood Cottage is a cottage in Stockbridge, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Beachwood Cottage

Beachwood Cottage is a cottage in Stockbridge, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,405.

From$344/night
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Whistler's Inn Bed & Breakfast - Stockbridge, MA

Whistler's Inn Bed & Breakfast

B & B, Stockbridge

Whistler's Inn Bed & Breakfast is a b & b in Stockbridge, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

Read more

About Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast is a b & b in Stockbridge, 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 breakfast, free wifi, kids friendly, kids friendly videos or books, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,678.

From$215/night
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