Vacation rentals in Sheffield, MA

Best vacation rentals and Airbnb offers in Sheffield, MA

10 ★ 1 reviews

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

Cottage, Sheffield

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns is a cottage in Sheffield, with pet-friendly space and kitchen access. 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 cottage in Sheffield, 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, Sheffield

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

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About Berkshire Riverfront Ski Cabin: Close to Hiking!

Berkshire Riverfront Ski Cabin: Close to Hiking! is a holiday home in Sheffield, 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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Downtown Great Barrington Enjoy Mountain Views

Holiday Home, Sheffield

Downtown Great Barrington Enjoy Mountain Views is a holiday home in Sheffield, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Downtown Great Barrington Enjoy Mountain Views

Downtown Great Barrington Enjoy Mountain Views is a holiday home in Sheffield, 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 ac.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $4,572.

From$534/night

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Water-View Home in the Berkshires

Holiday Home, Sheffield

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

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About Water-View Home in the Berkshires

Water-View Home in the Berkshires is a holiday home in Sheffield, 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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Family-friendly vacation rentals in Sheffield, MA

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

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

Cottage, Sheffield

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks is a cottage in Sheffield, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks

Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks is a cottage in Sheffield, 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 $3,396.

From$395/night

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Dog-friendly Copake Home w/ Sauna!

Cottage, Sheffield

Dog-friendly Copake Home w/ Sauna! is a cottage in Sheffield, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Dog-friendly Copake Home w/ Sauna!

Dog-friendly Copake Home w/ Sauna! is a cottage in Sheffield, 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 $4,546.

From$503/night

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Lakefront Otis Home w/ Stunning Views & Boats!

Cottage, Sheffield

Lakefront Otis Home w/ Stunning Views & Boats! is a cottage in Sheffield, 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 Sheffield, 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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Renovated Lakefront House w/ Dock: Pets Welcome!

Cottage, Sheffield

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

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About Renovated Lakefront House w/ Dock: Pets Welcome!

Renovated Lakefront House w/ Dock: Pets Welcome! is a cottage in Sheffield, 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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