Vacation rentals in Pittsfield, MA

Best vacation rentals and Airbnb offers in Pittsfield, MA

Vacation Village in the Berkshires

Condo, Pittsfield

Vacation Village in the Berkshires is a condo in Pittsfield, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Vacation Village in the Berkshires

Vacation Village in the Berkshires is a condo in Pittsfield, 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: pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $959.

From$113/night

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Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak

Apartment, Pittsfield

Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak is a apartment in Pittsfield, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak

Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak is a apartment in Pittsfield, with pool 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, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,162.

From$136/night

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Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4

Apartment, Pittsfield

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 is a apartment in Pittsfield, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 is a apartment in Pittsfield, with pool 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, pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,086.

From$136/night

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Ski-In/Ski-Out at Jiminy Peak in the Country Inn

Condo, Pittsfield

Ski-In/Ski-Out at Jiminy Peak in the Country Inn is a condo in Pittsfield, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Ski-In/Ski-Out at Jiminy Peak in the Country Inn

Ski-In/Ski-Out at Jiminy Peak in the Country Inn is a condo in Pittsfield, 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: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,055.

From$151/night

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Vacation rentals with a pool in Pittsfield, MA

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

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Apartment, Pittsfield

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor is a apartment in Pittsfield, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor is a apartment in Pittsfield, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,222.

From$175/night

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Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Apartment, Pittsfield

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn is a apartment in Pittsfield, with pool access, kitchen access, and room for a group. This stay gives…

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About Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn is a apartment in Pittsfield, 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: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,222.

From$175/night

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Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Apartment, Pittsfield

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4 is a apartment in Pittsfield, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4 is a apartment in Pittsfield, 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: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,222.

From$175/night

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Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby

Apartment, Pittsfield

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby is a apartment in Pittsfield, with pool access and kitchen access. This stay gives travelers a comfortable…

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About Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby is a apartment in Pittsfield, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,222.

From$175/night

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Vacation rentals with parking in Pittsfield, MA

Find vacation rentals that make arriving by car easier.

Charming 3-bedroom Ski house in Hancock 2.5 Miles from Jimmy Peak

Holiday Home, Pittsfield

Charming 3-bedroom Ski house in Hancock 2.5 Miles from Jimmy Peak is a holiday home in Pittsfield, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Charming 3-bedroom Ski house in Hancock 2.5 Miles from Jimmy Peak

Charming 3-bedroom Ski house in Hancock 2.5 Miles from Jimmy Peak is a holiday home in Pittsfield, 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 $1,289.

From$184/night

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Lenox in-law studio

Apartment, Pittsfield

Lenox in-law studio is a apartment in Pittsfield, 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 Pittsfield, 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 $1,293.

From$185/night

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NEW RENO - Historic Loft w/views of the Berkshires

Country House, Pittsfield

NEW RENO - Historic Loft w/views of the Berkshires is a country house in Pittsfield, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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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 Pittsfield, 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 $1,367.

From$195/night

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Solomon Ely Homestead - Charming Pittsfield Stay

Holiday Home, Pittsfield

Solomon Ely Homestead - Charming Pittsfield Stay is a holiday home in Pittsfield, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Solomon Ely Homestead - Charming Pittsfield Stay

Solomon Ely Homestead - Charming Pittsfield Stay is a holiday home in Pittsfield, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,023.

From$432/night

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Pet-friendly vacation rentals in Pittsfield, MA

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

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Cottage, Pittsfield

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck is a cottage in Pittsfield, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck is a cottage in Pittsfield, with pet-friendly space, outdoor 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 $2,046.

From$224/night

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Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)

Condo, Pittsfield

Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox) is a condo in Pittsfield, with pet-friendly space and kitchen access. This stay gives travelers a…

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About Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox)

Cozy Modern Berkshires Condo (mins from Kripalu, Tanglewood, Great Barr & Lenox) is a condo in Pittsfield, 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 $1,578.

From$225/night

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8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Holiday Home, Pittsfield

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck is a holiday home in Pittsfield, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

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About 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck is a holiday home in Pittsfield, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,716.

From$245/night

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Whistler's Inn

B & B, Pittsfield

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

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About Whistler's Inn

Whistler's Inn is a b & b in Pittsfield, with pet-friendly space and 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 breakfast, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,051.

From$262/night

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Vacation rentals with a kitchen in Pittsfield, MA

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

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Apartment, Pittsfield

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated is a apartment in Pittsfield, with pool access, kitchen access, and room for a group. This stay gives travelers…

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About Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated is a apartment in Pittsfield, 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: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,222.

From$175/night

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Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Apartment, Pittsfield

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor is a apartment in Pittsfield, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor is a apartment in Pittsfield, 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 $1,222.

From$175/night

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Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Apartment, Pittsfield

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone is a apartment in Pittsfield, with pool access, kitchen access, and room for a group. This stay gives…

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About Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone is a apartment in Pittsfield, 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: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,222.

From$175/night

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NEW RENO - Chalet-style farm loft near Tanglewood

Country House, Pittsfield

NEW RENO - Chalet-style farm loft near Tanglewood is a country house in Pittsfield, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood is a country house in Pittsfield, 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 $1,487.

From$212/night

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Family-friendly vacation rentals in Pittsfield, MA

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

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Apartment, Pittsfield

2 Bed Berkshire Apt minutes to Jiminy Peak Ski is a apartment in Pittsfield, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski is a apartment in Pittsfield, 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: pet friendly, pets friendly, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,300.

From$186/night

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2 Bed Berkshire Getaway @ Stephentown Hotel

Apartment, Pittsfield

2 Bed Berkshire Getaway @ Stephentown Hotel is a apartment in Pittsfield, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 2 Bed Berkshire Getaway @ Stephentown Hotel

2 Bed Berkshire Getaway @ Stephentown Hotel is a apartment in Pittsfield, 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: pet friendly, pets friendly, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,405.

From$201/night

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Pine & Paddle | Pond Access • Kayaks

Cottage, Pittsfield

Pine & Paddle · Pond Access · Kayaks is a cottage in Pittsfield, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Pine & Paddle | Pond Access • Kayaks

Pine & Paddle · Pond Access · Kayaks is a cottage in Pittsfield, 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 $2,311.

From$330/night

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Whistler's Inn Bed & Breakfast

B & B, Pittsfield

Whistler's Inn Bed & Breakfast is a b & b in Pittsfield, 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 Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast is a b & b in Pittsfield, 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, kids friendly, kids friendly videos or books, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,678.

From$215/night

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