Vacation rentals in Stockbridge Bowl, MA

104 available vacation rental offers

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Best vacation rentals and Airbnb offers in Stockbridge Bowl, MA

Lenox in-law studio - Stockbridge Bowl, MA

Lenox in-law studio

Apartment, Stockbridge Bowl

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

Cozy Stockbridge Cabin - Walk to Beach & Lake!

Holiday Home, Stockbridge Bowl

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

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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 Bowl, 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 Bowl, MA

Downtown Gateway to the Berkshires. Walk to Everything.

Apartment, Stockbridge Bowl

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

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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 Bowl, 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 Bowl, MA

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

Condo, Stockbridge Bowl

Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox) is a condo in Stockbridge Bowl, 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 Bowl, 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 $1,578.

From$225/night
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Vacation rentals with a pool in Stockbridge Bowl, MA

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

Charming 2-bedroom apartment in Lee with fitness room, WiFi - Stockbridge Bowl, MA

Charming 2-bedroom apartment in Lee with fitness room, WiFi

Apartment, Stockbridge Bowl

Charming 2-bedroom apartment in Lee with fitness room, WiFi is a apartment in Stockbridge Bowl, with pool access, kitchen access, and room for a group. This stay gives travelers a…

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About Charming 2-bedroom apartment in Lee with fitness room, WiFi

Charming 2-bedroom apartment in Lee with fitness room, WiFi is a apartment in Stockbridge Bowl, 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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Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee - Stockbridge Bowl, MA

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

Apartment, Stockbridge Bowl

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

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

Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee is a apartment in Stockbridge Bowl, 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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Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee - Stockbridge Bowl, MA

Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee

Apartment, Stockbridge Bowl

Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee is a apartment in Stockbridge Bowl, with pool access, kitchen access, and room for a group. This stay gives travelers a…

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About Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee

Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee is a apartment in Stockbridge Bowl, 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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Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee - Stockbridge Bowl, MA

Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee

Apartment, Stockbridge Bowl

Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee is a apartment in Stockbridge Bowl, with pool access, kitchen access, and room for a group. This stay gives travelers a…

Read more

About Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee

Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee is a apartment in Stockbridge Bowl, 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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Vacation rentals with parking in Stockbridge Bowl, MA

Find vacation rentals that make arriving by car easier.

Chic corporate apartment in wonderful Pittsfield with AC, WiFi - Stockbridge Bowl, MA

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Apartment, Stockbridge Bowl

Chic corporate apartment in wonderful Pittsfield with AC, WiFi is a apartment in Stockbridge Bowl, with parking. This stay gives travelers a comfortable base for exploring the area,…

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About Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Chic corporate apartment in wonderful Pittsfield with AC, WiFi is a apartment in Stockbridge Bowl, 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: parking, free parking, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,085.

From$155/night
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2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness! - Stockbridge Bowl, MA

2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness!

Apartment, Stockbridge Bowl

2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness! is a apartment in Stockbridge Bowl, with parking, kitchen access, and room for a group. This stay gives…

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About 2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness!

2 bedroom Riverhouse in the Heart of the Berkshires! Summer & winter coziness! is a apartment in Stockbridge Bowl, 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 washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,737.

From$248/night
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Eastgate Inn B&B - Stockbridge Bowl, MA

Eastgate Inn B&B

B & B, Stockbridge Bowl

Eastgate Inn B&B is a b & b in Stockbridge Bowl, 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 Eastgate Inn B&B

Eastgate Inn B&B is a b & b in Stockbridge Bowl, 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 ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,565.

From$320/night
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Eastgate Inn B&B - Stockbridge Bowl, MA

Eastgate Inn B&B

B & B, Stockbridge Bowl

Eastgate Inn B&B is a b & b in Stockbridge Bowl, 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 Eastgate Inn B&B

Eastgate Inn B&B is a b & b in Stockbridge Bowl, 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, paid parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,565.

From$320/night
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Pet-friendly vacation rentals in Stockbridge Bowl, MA

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

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

Cozy 1-bedroom studio in serene Great Barrington with AC

Apartment, Stockbridge Bowl

Cozy 1-bedroom studio in serene Great Barrington with AC is a apartment in Stockbridge Bowl, 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 Bowl, 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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Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield - Stockbridge Bowl, MA

Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield

Apartment, Stockbridge Bowl

Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield is a apartment in Stockbridge Bowl, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers…

Read more

About Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield

Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield is a apartment in Stockbridge Bowl, 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: pet friendly, pets friendly, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,479.

From$211/night
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Lovely Lakefront Cottage, Peaceful Setting, Hiking And More - Stockbridge Bowl, MA

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More

Holiday Home, Stockbridge Bowl

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

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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 Bowl, 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 Bowl, MA

Spacious Comfortable Charming Family Farmhouse Great Location

Country House, Stockbridge Bowl

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

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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 Bowl, 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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Vacation rentals with a kitchen in Stockbridge Bowl, MA

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

NEW RENO - Historic Loft w/views of the Berkshires - Stockbridge Bowl, MA

NEW RENO - Historic Loft w/views of the Berkshires

Country House, Stockbridge Bowl

NEW RENO - Historic Loft w/views of the Berkshires is a country house in Stockbridge Bowl, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About NEW RENO - Historic Loft w/views of the Berkshires

NEW RENO - Historic Loft w/views of the Berkshires is a country house in Stockbridge Bowl, 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 $1,367.

From$195/night
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Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee - Stockbridge Bowl, MA

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

Apartment, Stockbridge Bowl

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

Read more

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 Bowl, 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 Bowl, MA

Tranquil Lakeside Escape in the Berkshires

Condo, Stockbridge Bowl

Tranquil Lakeside Escape in the Berkshires is a condo in Stockbridge Bowl, 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 Bowl, 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 Bowl, MA

Spacious Villa with Access to Various Amenities!

Villa, Stockbridge Bowl

Spacious Villa with Access to Various Amenities! is a villa in Stockbridge Bowl, 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 Bowl, 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 $2,411.

From$344/night
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Family-friendly vacation rentals in Stockbridge Bowl, MA

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

Mountain View Retreat in Hudson Valley near Berkshire Attractions - Stockbridge Bowl, MA

Mountain View Retreat in Hudson Valley near Berkshire Attractions

Cottage, Stockbridge Bowl

Mountain View Retreat in Hudson Valley near Berkshire Attractions is a cottage in Stockbridge Bowl, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Mountain View Retreat in Hudson Valley near Berkshire Attractions

Mountain View Retreat in Hudson Valley near Berkshire Attractions is a cottage in Stockbridge Bowl, 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 $1,785.

From$255/night
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Berkshire Mountain Cottage: in the Heart of the Berkshires - Stockbridge Bowl, MA

Berkshire Mountain Cottage: in the Heart of the Berkshires

Cottage, Stockbridge Bowl

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

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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 Bowl, 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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Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath - Stockbridge Bowl, MA

Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath

Holiday Home, Stockbridge Bowl

Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath is a holiday home in Stockbridge Bowl, with kitchen access and a quieter setting. This stay gives travelers…

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About Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath

Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath is a holiday home in Stockbridge Bowl, with 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 kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,045.

From$292/night
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Pine & Paddle | Pond Access • Kayaks - Stockbridge Bowl, MA

Pine & Paddle | Pond Access • Kayaks

Cottage, Stockbridge Bowl

Pine & Paddle · Pond Access · Kayaks is a cottage in Stockbridge Bowl, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Pine & Paddle | Pond Access • Kayaks

Pine & Paddle · Pond Access · Kayaks is a cottage in Stockbridge Bowl, 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 $2,311.

From$330/night
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