Vacation rentals in Sheffield, MA

Best Vacation rentals and Airbnb offers in Sheffield, MA

Cozy 1-bedroom studio in serene Great Barrington with AC

Apartment, Sheffield

Cozy 1-bedroom studio in serene Great Barrington with AC is a apartment in Sheffield, 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 Sheffield, 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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Restored Historic 1850s Barn \"Carriage House\" Studio @ Hillsdale Town Center

Holiday Home, Sheffield

Restored Historic 1850s Barn \"Carriage House\" Studio @ Hillsdale Town Center is a holiday home in Sheffield, with pet-friendly space and parking. This stay gives travelers a comfortable…

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About Restored Historic 1850s Barn \"Carriage House\" Studio @ Hillsdale Town Center

Restored Historic 1850s Barn \"Carriage House\" Studio @ Hillsdale Town Center 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 cancellation, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,051.

From$150/night

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

Apartment, Sheffield

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

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

Apartment, Sheffield

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

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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 Sheffield, 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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Browse Vacation Rentals with a Pool in Sheffield, MA

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

Villa with Access to Various Amenities

Villa, Sheffield

Villa with Access to Various Amenities is a villa in Sheffield, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Villa with Access to Various Amenities

Villa with Access to Various Amenities is a villa in Sheffield, 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 $1,877.

From$268/night

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

Apartment, Sheffield

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

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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 Sheffield, 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, AC in welcoming Lee

Apartment, Sheffield

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

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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 Sheffield, 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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A Fun Farmhouse Near Ski Butternut

Holiday Home, Sheffield

A Fun Farmhouse Near Ski Butternut is a holiday home in Sheffield, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About A Fun Farmhouse Near Ski Butternut

A Fun Farmhouse Near Ski Butternut is a holiday home in Sheffield, 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, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,331.

From$619/night

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Best Sheffield, MA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Nature Retreat Near Prospect Lake

Holiday Home, Sheffield

Nature Retreat Near Prospect Lake is a holiday home in Sheffield, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About Nature Retreat Near Prospect Lake

Nature Retreat Near Prospect Lake is a holiday home in Sheffield, with parking, 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: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,705.

From$386/night

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Steepletop: Nature Lover’s Paradise w/Rec Room

Holiday Home, Sheffield

Steepletop: Nature Lover’s Paradise w/Rec Room is a holiday home in Sheffield, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Steepletop: Nature Lover’s Paradise w/Rec Room

Steepletop: Nature Lover’s Paradise w/Rec Room is a holiday home 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,797.

From$400/night

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Hilltop Escape with Views & Hot Tub

Holiday Home, Sheffield

Hilltop Escape with Views & Hot Tub is a holiday home in Sheffield, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Hilltop Escape with Views & Hot Tub

Hilltop Escape with Views & Hot Tub is a holiday home 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: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,113.

From$445/night

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Bellhaven- Charming 4-bedroom house in Canaan, CT

Holiday Home, Sheffield

Bellhaven- Charming 4-bedroom house in Canaan, CT is a holiday home in Sheffield, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Bellhaven- Charming 4-bedroom house in Canaan, CT

Bellhaven- Charming 4-bedroom house in Canaan, CT is a holiday home in Sheffield, 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,203.

From$458/night

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Best Pet-Friendly Vacation Rentals in Sheffield, MA

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

Cozy Cabin in the Berkshires

Cabin, Sheffield

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

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About Cozy Cabin in the Berkshires

Cozy Cabin in the Berkshires is a cabin 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,761.

From$252/night

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Luxurious & Modern 3 BR 1.5 Bath Log Cabin

Cabin, Sheffield

Luxurious & Modern 3 BR 1.5 Bath Log Cabin is a cabin in Sheffield, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Luxurious & Modern 3 BR 1.5 Bath Log Cabin

Luxurious & Modern 3 BR 1.5 Bath Log Cabin is a cabin in Sheffield, 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: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,224.

From$318/night

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Best of the Berkshires + Hot Tub by Evergreen Home

Holiday Home, Sheffield

Best of the Berkshires + Hot Tub by Evergreen Home is a holiday home in Sheffield, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Best of the Berkshires + Hot Tub by Evergreen Home

Best of the Berkshires + Hot Tub by Evergreen Home is a holiday home in Sheffield, 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,949.

From$421/night

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Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Holiday Home, Sheffield

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions is a holiday home in Sheffield, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions is a holiday home in Sheffield, 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 $4,007.

From$572/night

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Best Sheffield, MA vacation rentals with a kitchen

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

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

Apartment, Sheffield

Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee is a apartment in Sheffield, 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 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 Sheffield, 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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Charming 3-bedroom house with AC, WiFi in quaint Hillsdale

Holiday Home, Sheffield

Charming 3-bedroom house with AC, WiFi in quaint Hillsdale is a holiday home in Sheffield, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Charming 3-bedroom house with AC, WiFi in quaint Hillsdale

Charming 3-bedroom house with AC, WiFi in quaint Hillsdale is a holiday home in Sheffield, 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, kids friendly, kids friendly videos or books, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,096.

From$299/night

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Scoville Estate Millhouse w Bubbling Brook + Screened Porch on 5 Private Acres

Holiday Home, Sheffield

Scoville Estate Millhouse w Bubbling Brook + Screened Porch on 5 Private Acres is a holiday home in Sheffield, with kitchen access. This stay gives travelers a comfortable base for…

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About Scoville Estate Millhouse w Bubbling Brook + Screened Porch on 5 Private Acres

Scoville Estate Millhouse w Bubbling Brook + Screened Porch on 5 Private Acres is a holiday home in Sheffield, 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,928.

From$418/night

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Private Berkshires Getaway Minutes to Ski Butternut

Holiday Home, Sheffield

Private Berkshires Getaway Minutes to Ski Butternut is a holiday home in Sheffield, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Private Berkshires Getaway Minutes to Ski Butternut

Private Berkshires Getaway Minutes to Ski Butternut is a holiday home 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,253.

From$465/night

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Our Favorite Family-Friendly Vacation Rentals in Sheffield, MA

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

Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires

Cottage, Sheffield

Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires is a cottage in Sheffield, 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 Sheffield, 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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Cottage is currently rented for the year, and not available until further notice

Cottage, Sheffield

Cottage is currently rented for the year, and not available until further notice is a cottage in Sheffield, with pet-friendly space. This stay gives travelers a comfortable base for…

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About Cottage is currently rented for the year, and not available until further notice

Cottage is currently rented for the year, and not available until further notice is a cottage in Sheffield, 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, pet friendly, pets friendly, heating, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,995.

From$285/night

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Scribe`s Stable | A/C • Screened in Porch • Sleeps 6

Country House, Sheffield

Scribe`s Stable · A/C · Screened in Porch · Sleeps 6 is a country house in Sheffield, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Scribe`s Stable | A/C • Screened in Porch • Sleeps 6

Scribe`s Stable · A/C · Screened in Porch · Sleeps 6 is a country house in Sheffield, with parking 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, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,996.

From$285/night

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Family vacation home in Great Barrington

Holiday Home, Sheffield

Family vacation home in Great Barrington is a holiday home in Sheffield, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Family vacation home in Great Barrington

Family vacation home in Great Barrington is a holiday home in Sheffield, 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: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,077.

From$440/night

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