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 Great Barrington
4.95 out of 5 average rating, 317 reviewsPrivate En Suite in Beautiful Victorian
Mar 7 – 14
Home in Pittsfield
4.98 out of 5 average rating, 102 reviewsHidden Oasis in the Mountains by Evergreen Home
Apr 25 – May 2
Guest suite in Williamstown
4.96 out of 5 average rating, 202 reviewsBerkshire Guest Suite
Nov 13 – 20
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
Sep 4 – 11
Guesthouse in Stephentown
5.0 out of 5 average rating, 359 reviewsDog Friendly Studio
Mar 16 – 23
Apartment in Plainfield
4.97 out of 5 average rating, 238 reviewsSunny, light filled loft in 1873 Colonial
Feb 26 – Mar 5
Apartment in Lee
4.78 out of 5 average rating, 106 reviewsCozy Berkshire Cottage Style Apartment
Jun 6 – 13
Loft in East Nassau
4.99 out of 5 average rating, 151 reviewsDog Friendly Farm Spring bird watching
Sep 15 – 22
Other great vacation rentals in Pittsfield
Apartment in Pittsfield
4.86 out of 5 average rating, 42 reviewsThe Sunset Sanctuary - King Bed with Kitchen
Mar 15 – 22
Apartment in Pittsfield
4.96 out of 5 average rating, 48 reviewsThe sweet place in the beautiful Berkshires!
Dec 7 – 14
Apartment in Pittsfield
5.0 out of 5 average rating, 41 reviewsSimply off North
Nov 11 – 18
Cottage in Pittsfield
4.9 out of 5 average rating, 69 reviewsCottage Getaway - access all the Berkshires offer!
May 28 – Jun 4
Guesthouse in Pittsfield
4.98 out of 5 average rating, 47 reviewsThe Nest at Birdland
Sep 10 – 17
Apartment in Canaan
5.0 out of 5 average rating, 83 reviewsMountain View Getaway
Jan 29 – Feb 5
Apartment in Lanesborough
4.85 out of 5 average rating, 62 reviewsCharming Apt. in 18th c. Berkshire Farmhouse
Feb 5 – 12
Guest suite in Great Barrington
5.0 out of 5 average rating, 43 reviewsSweet 1-bedroom with salt water pool
Jun 6 – 13
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
€ 9 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 cottage rentals in Pittsfield have wifi?
Absolutely! We offer over 10 cottage 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 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 cottage rentals in Pittsfield have air conditioning?
Absolutely! We offer over 10 cottage 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 Cottage Rentals in Pittsfield?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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