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Pittsfield vacation rentals

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Pittsfield vacation rentals

Gym
BBQ grill
Laptop-friendly workspace
Wifi
Air conditioning

Stay near Pittsfield's top sights

Hancock Shaker Village161 locals recommend
Bousquet Ski Area115 locals recommend
Berkshire Museum102 locals recommend
Big Y World Class Market80 locals recommend
Ashuwillticook Rail Trail74 locals recommend
Barrington Stage Company64 locals recommend

Other great vacation rentals in Pittsfield

Guest favorite

Home in Athens

5 out of 5 average rating, 34 reviews

Perfect home for a getaway from NYC

Guest favorite

Home in Hillsdale

5 out of 5 average rating, 47 reviews

Lakefront close to ski & shopping

Superhost

Condo in West Dover

4.75 out of 5 average rating, 132 reviews

Beautiful condo 2.5 miles from Mount Snow

Guest favorite

Home in Charlemont

4.94 out of 5 average rating, 51 reviews

Tall Pines Rental

Guest favorite

Home in Hillsdale

4.95 out of 5 average rating, 41 reviews

Amazing Ski Rental: Big Views + Wood Stove

Guest favorite

Home in Wilmington

4.86 out of 5 average rating, 96 reviews

MtSnow * Hot Tub * Pool * Air Hockey * PingPong * Darts * 16ppl

Guest favorite

Home in Dover

4.87 out of 5 average rating, 63 reviews

Large Mount Snow Ski House with Hot Tub

Guest favorite

Home in Averill Park

4.95 out of 5 average rating, 153 reviews

Cozy, peaceful lake house close to Jiminy Peak

Show all

Quick stats about vacation rentals in Pittsfield

  • Total rentals

    210 properties

  • Nightly prices starting at

    $10 before taxes and fees

  • Total number of reviews

    7.9K reviews

  • Family-friendly rentals

    110 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with a pool

    20 properties have a pool

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Pittsfield?

    Yes! Work meets play with ease at over 110 vacation rentals in Pittsfield featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Pittsfield?

    Four-legged friends are welcome in Pittsfield. Choose from more than 70 vacation rentals for guests traveling with pets.

  • Are there Pittsfield vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Pittsfield, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Pittsfield have wifi?

    Absolutely! We offer over 80 house rentals with wifi in Pittsfield. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly apartment rentals in Pittsfield?

    Pittsfield has more than 20 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Pittsfield have a bbq area?

    Absolutely! We offer over 10 apartment rentals with a bbq area in Pittsfield. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in apartment rentals in Pittsfield?

    Experience the best of Pittsfield with our apartment rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do bed and breakfast rentals in Pittsfield have air conditioning?

    Absolutely! We offer over 10 bed and breakfast rentals with air conditioning in Pittsfield. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Pittsfield have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Pittsfield. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Bed And Breakfast Rentals in Pittsfield?

    Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

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