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
Guest suite in Williamstown
4.96 out of 5 average rating, 202 reviewsBerkshire Guest Suite
Dec 12 – 19
Home in Pittsfield
4.98 out of 5 average rating, 102 reviewsHidden Oasis in the Mountains by Evergreen Home
Jan 5 – 12
Apartment in Petersburg
4.85 out of 5 average rating, 147 reviewsThe Beer Diviner Brewery Apartment
Feb 16 – 23
Home in Lee
4.89 out of 5 average rating, 235 reviewsCozy Berkshires Cottage
Oct 4 – 11
Tiny home in Chatham
4.99 out of 5 average rating, 181 reviewsTiny House on 70 Private Acres in Hudson Valley
Aug 9 – 16
Cottage in Lanesborough
4.93 out of 5 average rating, 220 reviewsStone School Cottage
Sep 8 – 15
Guest suite in Valatie
4.98 out of 5 average rating, 230 reviewsGuest Suite in Old Chatham Hunt Country
Sep 16 – 23
Cabin in Savoy
4.98 out of 5 average rating, 186 reviewsThe Camp - 20 Minutes to Berkshire East!
Sep 2 – 9
Other great vacation rentals in Pittsfield
Guest suite in Austerlitz
4.86 out of 5 average rating, 137 reviewsRustic-Modern Studio - Near Hudson, Chatham, & GB
Oct 8 – 15
Cabin in Canaan
4.99 out of 5 average rating, 231 reviewsRustic Barn Studio Apartment
Oct 12 – 19
Apartment in Pittsfield
4.86 out of 5 average rating, 42 reviewsThe Sunset Sanctuary - King Bed with Kitchen
Dec 22 – 29
Apartment in Pittsfield
4.92 out of 5 average rating, 25 reviewsComfortable Pittsfield Loft
Nov 11 – 18
Apartment in Pittsfield
4.83 out of 5 average rating, 18 reviewsCozy Studio Apt in Downtown Victorian
Jul 5 – 12
Apartment in Canaan
5.0 out of 5 average rating, 86 reviewsMountain View Getaway
Jan 20 – 27
Cottage in Pittsfield
4.9 out of 5 average rating, 69 reviewsCottage Getaway - access all the Berkshires offer!
May 31 – Jun 7
Apartment in Pittsfield
4.96 out of 5 average rating, 48 reviewsThe sweet place in the beautiful Berkshires!
Dec 9 – 16
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 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 apartment rentals in Pittsfield have air conditioning?
Absolutely! We offer over 60 apartment 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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