Pittsfield vacation rentals
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
Apartment in Plainfield
4.95 out of 5 average rating, 238 reviewsSunny carriage house apartment
Apartment in Petersburg
4.85 out of 5 average rating, 150 reviewsThe Beer Diviner Brewery Apartment
Apartment in Copake Falls
4.93 out of 5 average rating, 262 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
Home in Pittsfield
4.94 out of 5 average rating, 101 reviewsCantabile life in the Berkshires
Home in Pittsfield
4.98 out of 5 average rating, 102 reviewsHidden Oasis in the Mountains by Evergreen Home
Cabin in Canaan
4.99 out of 5 average rating, 231 reviewsRustic Barn Studio Apartment
Cottage in Kinderhook
4.98 out of 5 average rating, 175 reviewsThe Cottage on Sylvester Street
Cottage in Lanesborough
4.93 out of 5 average rating, 220 reviewsStone School Cottage
Other great vacation rentals in Pittsfield
Apartment in North Adams
4.96 out of 5 average rating, 426 reviewsSteps to MoCA, 2bd + SAUNA!
Apartment in Pittsfield
4.86 out of 5 average rating, 42 reviewsThe Sunset Sanctuary - King Bed with Kitchen
Apartment in Pittsfield
4.93 out of 5 average rating, 27 reviewsComfortable Pittsfield Loft
Apartment in Pittsfield
4.96 out of 5 average rating, 49 reviewsThe sweet place in the beautiful Berkshires!
Apartment in Pittsfield
4.79 out of 5 average rating, 19 reviewsCozy Studio Apt in Downtown Victorian
Guesthouse in Pittsfield
4.98 out of 5 average rating, 47 reviewsThe Nest at Birdland
Apartment in Canaan
5.0 out of 5 average rating, 90 reviewsMountain View Getaway
Home in Becket
4.95 out of 5 average rating, 38 reviewsNerd Preservation Sanctuary
Quick stats about vacation rentals in Pittsfield
Total rentals
210 properties
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
70 properties allow pets
Family-friendly rentals
120 properties are a good fit for families
Total number of reviews
7.1K reviews
Nightly prices starting at
$10 before taxes and fees
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 90 house 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 house rentals in Pittsfield have a bbq area?
Absolutely! We offer over 40 house 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 air conditioning?
Absolutely! We offer over 70 house 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 Apartment Rentals in Pittsfield?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 60 homes with air conditioning, over 10 homes with a bbq area, over 80 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
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