
Vacation rentals in Pittsfield
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Pittsfield
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield vacation rentals
Other great vacation rentals in Pittsfield

Beautiful Blue Studio downtown

Ohana House

Lakefront Home on Ponstoosuc Lake, The Berkshires

BB's Central Berkshire Home

Berkshires,pet friendly farm stay w/mountain views

Spacious 4 Br+ house in the heart of Berkshires

Pebbled Beach Cottage

The Cottage at The Barrington House
Quick stats about vacation rentals in Pittsfield
Total rentals
230 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
8.3K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
90 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 120 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 90 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 apartment rentals in Pittsfield have wifi?
Absolutely! We offer over 80 apartment rentals with wifi in Pittsfield. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Pittsfield?
Pittsfield has more than 70 family-friendly house 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 house rentals in Pittsfield?
Experience the best of Pittsfield with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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.
Do house rentals in Pittsfield have self check-in?
Absolutely! We offer over 30 house rentals with self check-in in Pittsfield. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Pittsfield?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 80 homes with wifi, over 10 homes with a bbq area, over 20 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.
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