Vacation rentals in The Berkshires, MA

Best vacation rentals and Airbnb offers in The Berkshires, MA

10 ★ 1 reviews

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Cottage, The Berkshires

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns is a cottage in The Berkshires, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns is a cottage in The Berkshires, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,263.

From$237/night

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Berkshire Riverfront Ski Cabin: Close to Hiking!

Holiday Home, The Berkshires

Berkshire Riverfront Ski Cabin: Close to Hiking! is a holiday home in The Berkshires, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the…

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About Berkshire Riverfront Ski Cabin: Close to Hiking!

Berkshire Riverfront Ski Cabin: Close to Hiking! is a holiday home in The Berkshires, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,667.

From$295/night

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Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Holiday Home, The Berkshires

Rustic Berkshires Cottage at Lake Buel w/ Kayaks! is a holiday home in The Berkshires, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the…

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About Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

Rustic Berkshires Cottage at Lake Buel w/ Kayaks! is a holiday home in The Berkshires, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,734.

From$177/night

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Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Holiday Home, The Berkshires

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns is a holiday home in The Berkshires, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns is a holiday home in The Berkshires, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,186.

From$202/night

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Family-friendly vacation rentals in The Berkshires, MA

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

The Cottage

B & B, The Berkshires

The Cottage is a b & b in The Berkshires, with pet-friendly space and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About The Cottage

The Cottage is a b & b in The Berkshires, with pet-friendly space and easy beach 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 breakfast, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,396.

From$312/night

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Water-view Home in the Berkshires

Cottage, The Berkshires

Water-view Home in the Berkshires is a cottage in The Berkshires, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Water-view Home in the Berkshires

Water-view Home in the Berkshires is a cottage in The Berkshires, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,782.

From$321/night

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Lakefront Otis Home w/ Stunning Views & Boats!

Cottage, The Berkshires

Lakefront Otis Home w/ Stunning Views & Boats! is a cottage in The Berkshires, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Lakefront Otis Home w/ Stunning Views & Boats!

Lakefront Otis Home w/ Stunning Views & Boats! is a cottage in The Berkshires, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,439.

From$517/night

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Family Lake Retreat Sauna, Deck & Games

Chalet, The Berkshires

Family Lake Retreat Sauna, Deck & Games is a chalet in The Berkshires, with outdoor space, room for a group, and a quieter setting. This stay gives travelers a comfortable base for…

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About Family Lake Retreat Sauna, Deck & Games

Family Lake Retreat Sauna, Deck & Games is a chalet in The Berkshires, with outdoor space, room for a group, 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, ac, air conditioning, heating, and bbq facilities.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,558.

From$572/night

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Pet-friendly vacation rentals in The Berkshires, MA

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

Summer and Fall in Sheffield with Monthly Special Pricing Available

Holiday Home, The Berkshires

Summer and Fall in Sheffield with Monthly Special Pricing Available is a holiday home in The Berkshires, with pet-friendly space and pool access. This stay gives travelers a comfortable…

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About Summer and Fall in Sheffield with Monthly Special Pricing Available

Summer and Fall in Sheffield with Monthly Special Pricing Available is a holiday home in The Berkshires, 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: pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,939.

From$344/night

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Massachusetts Lake House w/ Dock - Pets Welcome!

Holiday Home, The Berkshires

Massachusetts Lake House w/ Dock - Pets Welcome! is a holiday home in The Berkshires, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Massachusetts Lake House w/ Dock - Pets Welcome!

Massachusetts Lake House w/ Dock - Pets Welcome! is a holiday home in The Berkshires, 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, free wifi, pet friendly, pets friendly, and gym.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $5,054.

From$589/night

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Renovated Lakefront House w/ Dock: Pets Welcome!

Cottage, The Berkshires

Renovated Lakefront House w/ Dock: Pets Welcome! is a cottage in The Berkshires, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Renovated Lakefront House w/ Dock: Pets Welcome!

Renovated Lakefront House w/ Dock: Pets Welcome! is a cottage in The Berkshires, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $5,250.

From$640/night

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Vacation rentals with parking in The Berkshires, MA

Find vacation rentals that make arriving by car easier.

Lakefront Otis Home w/ Stunning Views & Boats!

Holiday Home, The Berkshires

Lakefront Otis Home w/ Stunning Views & Boats! is a holiday home in The Berkshires, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Lakefront Otis Home w/ Stunning Views & Boats!

Lakefront Otis Home w/ Stunning Views & Boats! is a holiday home in The Berkshires, 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: hot tub, free wifi, parking, and paid parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,276.

From$471/night

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Water-View Home in the Berkshires

Holiday Home, The Berkshires

Water-View Home in the Berkshires is a holiday home in The Berkshires, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Water-View Home in the Berkshires

Water-View Home in the Berkshires is a holiday home in The Berkshires, 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, free wifi, parking, paid parking, and heating.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,681.

From$282/night

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Chambery Inn

B & B, The Berkshires

Chambery Inn is a b & b in The Berkshires, 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 Chambery Inn

Chambery Inn is a b & b in The Berkshires, 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, free wifi, for couples, wine or champagne, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,096.

From$396/night

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