Vacation rentals in Berkshire County, MA

Best vacation rentals and Airbnb offers in Berkshire County, MA

10 ★ 93 reviews

Remote and Relaxing Cabin in the Berkshires

Holiday Home, Berkshire County

Remote and Relaxing Cabin in the Berkshires is a holiday home in Berkshire County, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Remote and Relaxing Cabin in the Berkshires

Remote and Relaxing Cabin in the Berkshires is a holiday home in Berkshire County, 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: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,941.

From$277/night

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10 ★ 61 reviews

Berkshire Lake access

Holiday Home, Berkshire County

Berkshire Lake access 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…

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About Berkshire Lake access

Berkshire Lake access 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,676.

From$239/night

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10 ★ 25 reviews

2 Bedroom renovated townehouse, #5 , Beautifully decorated at Garfield House

Holiday Home, Berkshire County

2 Bedroom renovated townehouse, #5 , Beautifully decorated at Garfield House is a holiday home in Berkshire County, with pet-friendly space, parking, and kitchen access. This stay gives…

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About 2 Bedroom renovated townehouse, #5 , Beautifully decorated at Garfield House

2 Bedroom renovated townehouse, #5 , Beautifully decorated at Garfield House is a holiday home 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,404.

From$201/night

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10 ★ 16 reviews

Garfield Townhouse in the Berkshires on Main St

Holiday Home, Berkshire County

Garfield Townhouse in the Berkshires on Main St is a holiday home in Berkshire County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Garfield Townhouse in the Berkshires on Main St

Garfield Townhouse in the Berkshires on Main St 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,404.

From$201/night

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Family-friendly vacation rentals in Berkshire County, MA

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

9.8 ★ 31 reviews

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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,721.

From$389/night

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9.8 ★ 6 reviews

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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,106.

From$301/night

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9 ★ 2 reviews

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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,388.

From$198/night

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8 ★ 3 reviews

Hideaway Inn Lenox

Guest House, Berkshire County

Hideaway Inn Lenox is a guest house in Berkshire County, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Hideaway Inn Lenox

Hideaway Inn Lenox is a guest house 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 cancellation, free wifi, kids friendly, kids friendly videos or books, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,283.

From$292/night

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Pet-friendly vacation rentals in Berkshire County, MA

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

9.8 ★ 130 reviews

Serene, Private Waterfront House --Perfect Summer Retreat!

Holiday Home, Berkshire County

Serene, Private Waterfront House --Perfect Summer Retreat! is a holiday home in Berkshire County, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a…

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About Serene, Private Waterfront House --Perfect Summer Retreat!

Serene, Private Waterfront House --Perfect Summer Retreat! is a holiday home 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 cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,387.

From$341/night

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9.6 ★ 23 reviews

Pristine Home In Becket Woods

Holiday Home, Berkshire County

Pristine Home In Becket Woods is a holiday home 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 Pristine Home In Becket Woods

Pristine Home In Becket Woods is a holiday home 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,831.

From$262/night

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8 ★ 1 reviews

Berkshires' best! Tanglewood, Jacob's Pillow and 400 feet from a pristine lake

Holiday Home, Berkshire County

Berkshires' best! Tanglewood, Jacob's Pillow and 400 feet from a pristine lake is a holiday home in Berkshire County, with pet-friendly space, parking, and kitchen access. This stay gives…

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About Berkshires' best! Tanglewood, Jacob's Pillow and 400 feet from a pristine lake

Berkshires' best! Tanglewood, Jacob's Pillow and 400 feet from a pristine lake is a holiday home 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,091.

From$299/night

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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 cancellation, free breakfast, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,836.

From$235/night

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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.

10 ★ 2 reviews

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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,533.

From$219/night

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9.8 ★ 22 reviews

Spacious Villa with Access to Various Amenities!

Villa, Berkshire County

Spacious Villa with Access to Various Amenities! is a villa in Berkshire County, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Spacious Villa with Access to Various Amenities!

Spacious Villa with Access to Various Amenities! is a villa 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, hot tub, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,914.

From$273/night

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9 ★ 18 reviews

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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,422.

From$203/night

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10 ★ 138 reviews

Devonfield Inn B&B

B & B, Berkshire County

Devonfield Inn B&B is a b & b in Berkshire County, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Devonfield Inn B&B

Devonfield Inn B&B is a b & b in Berkshire County, with pool 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 breakfast, pool, free wifi, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,433.

From$439/night

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Vacation rentals with parking in Berkshire County, MA

Find vacation rentals that make arriving by car easier.

10 ★ 47 reviews

1500 sqft private entrance with beautiful views of the Berkshire Mountains

Apartment, Berkshire County

1500 sqft private entrance with beautiful views of the Berkshire Mountains is a apartment in Berkshire County, with parking and kitchen access. This stay gives travelers a comfortable base…

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About 1500 sqft private entrance with beautiful views of the Berkshire Mountains

1500 sqft private entrance with beautiful views of the Berkshire Mountains 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, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,293.

From$328/night

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10 ★ 24 reviews

Clean & Modern space with a mix of original warmth and charming renovation.

Apartment, Berkshire County

Clean & Modern space with a mix of original warmth and charming renovation. is a apartment in Berkshire County, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Clean & Modern space with a mix of original warmth and charming renovation.

Clean & Modern space with a mix of original warmth and charming renovation. 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, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,699.

From$243/night

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9.6 ★ 20 reviews

Artist's Camp on Lake Mahkeenac

Cabin, Berkshire County

Artist's Camp on Lake Mahkeenac is a cabin in Berkshire County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Artist's Camp on Lake Mahkeenac

Artist's Camp on Lake Mahkeenac is a cabin 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: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,987.

From$284/night

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9.6 ★ 377 reviews

Chambery Inn

B & B, Berkshire County

Chambery Inn 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…

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About Chambery Inn

Chambery Inn 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 cancellation, hot tub, free wifi, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $3,063.

From$392/night

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Vacation rentals with a kitchen in Berkshire County, MA

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

10 ★ 1 reviews

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…

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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 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,533.

From$219/night

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10 ★ 1 reviews

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, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,258.

From$323/night

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9.8 ★ 24 reviews

Charming home in private Beachwood Community on Lake Mahkeenac, Stockbridge

Holiday Home, Berkshire County

Charming home in private Beachwood Community on Lake Mahkeenac, Stockbridge is a holiday home in Berkshire County, with pet-friendly space, easy beach access, and kitchen access. This stay…

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About Charming home in private Beachwood Community on Lake Mahkeenac, Stockbridge

Charming home in private Beachwood Community on Lake Mahkeenac, Stockbridge is a holiday home 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 cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,745.

From$392/night

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8 ★ 2 reviews

Peaceful 1BR Condo with Pond View

Condo, Berkshire County

Peaceful 1BR Condo with Pond View is a condo in Berkshire County, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Peaceful 1BR Condo with Pond View

Peaceful 1BR Condo with Pond View is a condo in Berkshire County, with pool 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, pool, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,826.

From$261/night

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