Vacation rentals in Great Barrington, MA

Best Vacation rentals and Airbnb offers in Great Barrington, MA

Cozy 1-bedroom studio in serene Great Barrington with AC

Apartment, Great Barrington

Cozy 1-bedroom studio in serene Great Barrington with AC is a apartment in Great Barrington, 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 Great Barrington, 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 $944.

From$104/night

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

Holiday Home, Great Barrington

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

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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 Great Barrington, 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 $1,173.

From$116/night

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

Apartment, Great Barrington

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

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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 Great Barrington, 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 $1,716.

From$190/night

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5 Minutes from The Appalachian Trail and Mount Washington. In the Berkshires!

Holiday Home, Great Barrington

5 Minutes from The Appalachian Trail and Mount Washington. In the Berkshires! is a holiday home in Great Barrington, with pet-friendly space and kitchen access. This stay gives travelers a…

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About 5 Minutes from The Appalachian Trail and Mount Washington. In the Berkshires!

5 Minutes from The Appalachian Trail and Mount Washington. In the Berkshires! is a holiday home in Great Barrington, 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, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,016.

From$197/night

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Browse Vacation Rentals with a Pool in Great Barrington, 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, Great Barrington

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

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About Villa with Access to Various Amenities

Villa with Access to Various Amenities is a villa in Great Barrington, 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 $1,959.

From$220/night

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

Apartment, Great Barrington

Charming 2-bedroom apartment in Lee with fitness room, WiFi is a apartment in Great Barrington, 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 Great Barrington, 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 $2,278.

From$261/night

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

Apartment, Great Barrington

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

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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 Great Barrington, 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 $2,278.

From$261/night

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A Fun Farmhouse Near Ski Butternut

Holiday Home, Great Barrington

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

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About A Fun Farmhouse Near Ski Butternut

A Fun Farmhouse Near Ski Butternut is a holiday home in Great Barrington, 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 $4,841.

From$502/night

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Best Great Barrington, MA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Lenox in-law studio

Apartment, Great Barrington

Lenox in-law studio is a apartment in Great Barrington, 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 Great Barrington, 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 $1,443.

From$150/night

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Cozy Stockbridge Cabin - Walk to Beach & Lake!

Cabin, Great Barrington

Cozy Stockbridge Cabin - Walk to Beach & Lake! is a cabin in Great Barrington, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Cozy Stockbridge Cabin - Walk to Beach & Lake!

Cozy Stockbridge Cabin - Walk to Beach & Lake! is a cabin in Great Barrington, with easy beach 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,969.

From$173/night

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Cozy Stockbridge Cabin - Walk to Beach & Lake!

Holiday Home, Great Barrington

Cozy Stockbridge Cabin - Walk to Beach & Lake! is a holiday home in Great Barrington, 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 Great Barrington, 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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Charming Berkshire Bungalow: Deck, Firepit, Stargazing

Holiday Home, Great Barrington

Charming Berkshire Bungalow: Deck, Firepit, Stargazing is a holiday home in Great Barrington, with outdoor space and parking. This stay gives travelers a comfortable base for exploring the…

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About Charming Berkshire Bungalow: Deck, Firepit, Stargazing

Charming Berkshire Bungalow: Deck, Firepit, Stargazing is a holiday home in Great Barrington, 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, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,593.

From$277/night

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Best Pet-Friendly Vacation Rentals in Great Barrington, MA

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

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More

Holiday Home, Great Barrington

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More is a holiday home in Great Barrington, 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 Great Barrington, 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 $2,286.

From$257/night

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Saltbox-style residence in the Berkshires

Holiday Home, Great Barrington

Saltbox-style residence in the Berkshires is a holiday home in Great Barrington, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Saltbox-style residence in the Berkshires

Saltbox-style residence in the Berkshires is a holiday home in Great Barrington, 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, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,954.

From$302/night

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Prime Location, Recently Redesigned, Riverfront!

Holiday Home, Great Barrington

Prime Location, Recently Redesigned, Riverfront! is a holiday home in Great Barrington, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Prime Location, Recently Redesigned, Riverfront!

Prime Location, Recently Redesigned, Riverfront! is a holiday home in Great Barrington, 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: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,026.

From$392/night

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Historic, Modern Comforts, Walk To Downtown

Holiday Home, Great Barrington

Historic, Modern Comforts, Walk To Downtown is a holiday home in Great Barrington, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Historic, Modern Comforts, Walk To Downtown

Historic, Modern Comforts, Walk To Downtown is a holiday home in Great Barrington, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,530.

From$540/night

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Best Great Barrington, MA vacation rentals with a kitchen

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

Downtown Gateway to the Berkshires. Walk to Everything.

Apartment, Great Barrington

Downtown Gateway to the Berkshires. Walk to Everything. is a apartment in Great Barrington, 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 Great Barrington, 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 $1,664.

From$176/night

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

Apartment, Great Barrington

Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee is a apartment in Great Barrington, 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 Great Barrington, 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 $2,278.

From$261/night

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

Apartment, Great Barrington

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

Read more

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 Great Barrington, 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 $2,278.

From$261/night

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

Apartment, Great Barrington

Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee is a apartment in Great Barrington, 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 Great Barrington, 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 $2,278.

From$261/night

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Our Favorite Family-Friendly Vacation Rentals in Great Barrington, 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, Great Barrington

Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires is a cottage in Great Barrington, 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 Great Barrington, 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 $2,227.

From$225/night

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

Country House, Great Barrington

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

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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 Great Barrington, 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 $2,277.

From$231/night

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

Holiday Home, Great Barrington

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

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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 Great Barrington, 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 $2,372.

From$244/night

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Twin Maple Farm: Charming Modern Farmhouse

Holiday Home, Great Barrington

Twin Maple Farm: Charming Modern Farmhouse is a holiday home in Great Barrington, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Twin Maple Farm: Charming Modern Farmhouse

Twin Maple Farm: Charming Modern Farmhouse is a holiday home in Great Barrington, 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 wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,545.

From$356/night

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