Vacation rentals in Berkshire County, MA

75 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Berkshire County, MA

Chic corporate apartment in wonderful Pittsfield with AC, WiFi - Berkshire County, MA

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Apartment, Berkshire County

Chic corporate apartment in wonderful Pittsfield with AC, WiFi is a apartment in Berkshire County, 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 Berkshire County, 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 $1,212.

From$135/night
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Lenox in-law studio - Berkshire County, MA

Lenox in-law studio

Apartment, Berkshire County

Lenox in-law studio is a apartment in Berkshire County, 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 Berkshire County, 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 $1,444.

From$150/night
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Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield - Berkshire County, MA

Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield

Apartment, Berkshire County

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

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

Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield is a apartment in Berkshire County, 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 $1,412.

From$161/night
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Cozy Stockbridge Cabin - Walk to Beach & Lake! - Berkshire County, MA

Cozy Stockbridge Cabin - Walk to Beach & Lake!

Cabin, Berkshire County

Cozy Stockbridge Cabin - Walk to Beach & Lake! is a cabin in Berkshire County, 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 Berkshire County, 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 $1,970.

From$173/night
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Browse Vacation Rentals with a Pool in Berkshire County, MA

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

Villa with Access to Various Amenities - Berkshire County, MA

Villa with Access to Various Amenities

Villa, Berkshire County

Villa with Access to Various Amenities is a villa in Berkshire County, 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 Berkshire County, 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 $1,954.

From$220/night
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Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee - Berkshire County, MA

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

Apartment, Berkshire County

Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee is a apartment in Berkshire County, 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 Berkshire County, 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 $2,279.

From$261/night
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Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee - Berkshire County, MA

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

Apartment, Berkshire County

Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee is a apartment in Berkshire County, 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 Berkshire County, 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 $2,279.

From$261/night
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Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee - Berkshire County, MA

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

Apartment, Berkshire County

Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee is a apartment in Berkshire County, 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 WiFi, fitness room in enjoyable Lee

Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee is a apartment in Berkshire County, 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 $2,279.

From$261/night
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Best Berkshire County, MA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

NEW RENO - Historic Loft w/views of the Berkshires - Berkshire County, MA

NEW RENO - Historic Loft w/views of the Berkshires

Country House, Berkshire County

NEW RENO - Historic Loft w/views of the Berkshires is a country house in Berkshire County, 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 Berkshire County, 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 $1,462.

From$177/night
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Eastgate Inn B&B - Berkshire County, MA

Eastgate Inn B&B

B & B, Berkshire County

Eastgate Inn B&B is a b & b in Berkshire County, 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 Berkshire County, 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 fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,477.

From$317/night
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Eastgate Inn B&B - Berkshire County, MA

Eastgate Inn B&B

B & B, Berkshire County

Eastgate Inn B&B is a b & b in Berkshire County, 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 Berkshire County, 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 - Berkshire County, MA

Eastgate Inn B&B

B & B, Berkshire County

Eastgate Inn B&B is a b & b in Berkshire County, 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 Berkshire County, 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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Best Pet-Friendly Vacation Rentals in Berkshire County, MA

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

Beachwood Cottage - Berkshire County, MA

Beachwood Cottage

Cottage, Berkshire County

Beachwood Cottage is a cottage in Berkshire County, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Beachwood Cottage

Beachwood Cottage is a cottage in Berkshire County, with pet-friendly space, easy beach 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,686.

From$280/night
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Timpani Corners | Private Pond • AC - Berkshire County, MA

Timpani Corners | Private Pond • AC

Cabin, Berkshire County

Timpani Corners · Private Pond · AC is a cabin in Berkshire County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Timpani Corners | Private Pond • AC

Timpani Corners · Private Pond · AC is a cabin in Berkshire County, 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 $2,791.

From$289/night
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Spacious Comfortable Charming Family Farmhouse Great Location - Berkshire County, MA

Spacious Comfortable Charming Family Farmhouse Great Location

Country House, Berkshire County

Spacious Comfortable Charming Family Farmhouse Great Location is a country house in Berkshire County, 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 Berkshire County, 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 $3,057.

From$325/night
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Whistler's Inn - Berkshire County, MA

Whistler's Inn

B & B, Berkshire County

Whistler's Inn is a b & b in Berkshire County, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Whistler's Inn

Whistler's Inn is a b & b in Berkshire County, 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 breakfast, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,279.

From$291/night
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Best Berkshire County, MA vacation rentals with a kitchen

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

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

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

Apartment, Berkshire County

Charming 2-bedroom apartment in Lee with fitness room, WiFi is a apartment in Berkshire County, 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 Berkshire County, 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 $2,279.

From$261/night
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Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee - Berkshire County, MA

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

Apartment, Berkshire County

Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee is a apartment in Berkshire County, 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 Berkshire County, 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 $2,279.

From$261/night
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Tranquil Lakeside Escape in the Berkshires - Berkshire County, MA

Tranquil Lakeside Escape in the Berkshires

Condo, Berkshire County

Tranquil Lakeside Escape in the Berkshires is a condo in Berkshire County, 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 Berkshire County, 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 $2,693.

From$305/night
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Cozy Home in Lenox - Berkshire County, MA

Cozy Home in Lenox

Holiday Home, Berkshire County

Cozy Home in Lenox is a holiday home in Berkshire County, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Cozy Home in Lenox

Cozy Home in Lenox is a holiday home in Berkshire County, 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 $3,104.

From$333/night
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Our Favorite Family-Friendly Vacation Rentals in Berkshire County, MA

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

Cozy Becket Cottage Escape w/ Lake Access! - Berkshire County, MA

Cozy Becket Cottage Escape w/ Lake Access!

Cottage, Berkshire County

Cozy Becket Cottage Escape w/ Lake Access! is a cottage in Berkshire County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cozy Becket Cottage Escape w/ Lake Access!

Cozy Becket Cottage Escape w/ Lake Access! is a cottage in Berkshire County, 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 $1,555.

From$140/night
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Cozy Stockbridge Cabin - Walk to Beach & Lake! - Berkshire County, MA

Cozy Stockbridge Cabin - Walk to Beach & Lake!

Cottage, Berkshire County

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

Read more

About Cozy Stockbridge Cabin - Walk to Beach & Lake!

Cozy Stockbridge Cabin - Walk to Beach & Lake! is a cottage in Berkshire County, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,097.

From$242/night
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Lovely Lakefront Cottage, Peaceful Setting, Hiking And More - Berkshire County, MA

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More

Holiday Home, Berkshire County

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More is a holiday home in Berkshire County, 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 Berkshire County, 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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Pine & Paddle | Pond Access • Kayaks - Berkshire County, MA

Pine & Paddle | Pond Access • Kayaks

Cottage, Berkshire County

Pine & Paddle · Pond Access · Kayaks is a cottage in Berkshire County, 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 Berkshire County, 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 $2,606.

From$278/night
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