Pittsfield vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Pittsfield vacation rentals

Stay near Pittsfield's top sights

Walmart9 locals recommend
Big Y World Class Market80 locals recommend
Berkshire Roots7 locals recommend
99 Restaurants7 locals recommend
Colonial Theatre56 locals recommend
Berkshire Museum102 locals recommend

Other great vacation rentals in Pittsfield

Guest favorite
Cottage in Great Barrington
Cottage on Scenic Road
Jun 16 – 23
$117 per night
4.91 out of 5 average rating, 223 reviews
Guest favorite
Guest suite in Williamstown
Berkshire Guest Suite
Dec 5 – 12
$88 per night
4.96 out of 5 average rating, 202 reviews
Guest favorite
Farm stay in New Lebanon
Barn Stay at Shadowbrook Farm
Aug 18 – 25
$182 per night
4.95 out of 5 average rating, 183 reviews
Guest favorite
Guesthouse in Stephentown
Dog Friendly Studio
Aug 5 – 12
$167 per night
5.0 out of 5 average rating, 356 reviews
Guest favorite
Guesthouse in Canaan
Airy cottage with meadow views in The Berkshires
Jan 2 – 9
$144 per night
4.93 out of 5 average rating, 166 reviews
Guest favorite
Apartment in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
Aug 29 – Sep 5
$92 per night
4.93 out of 5 average rating, 247 reviews
Guest favorite
Guest suite in Valatie
Guest Suite in Old Chatham Hunt Country
Mar 29 – Apr 5
$79 per night
4.98 out of 5 average rating, 229 reviews
Superhost
Cottage in Lanesborough
Wildlife Lakeside Cottage
Apr 10 – 17
$200 per night
4.85 out of 5 average rating, 246 reviews

Other great vacation rentals in Pittsfield

Guest favorite
Apartment in Lanesborough
Cozy Berkshire Waterfront Home
Apr 9 – 16
$138 per night
5.0 out of 5 average rating, 21 reviews
Guest favorite
Apartment in Canaan
Mountain View Getaway
Jan 10 – 17
$91 per night
5.0 out of 5 average rating, 81 reviews
Guest favorite
Condo in Hancock
Jiminy Peak Country Inn - ski in/out condo MT view
Apr 24 – May 1
$74 per night
4.9 out of 5 average rating, 51 reviews
Superhost
Apartment in Lanesborough
Charming Apt. in 18th c. Berkshire Farmhouse
Feb 12 – 19
$94 per night
4.85 out of 5 average rating, 62 reviews
Guest favorite
Apartment in Pittsfield
Charming Apartment inThe Heart of The Berkshires 2
Apr 7 – 14
$88 per night
4.8 out of 5 average rating, 70 reviews
Guest favorite
Apartment in Adams
Mountain Living, 1-bedroom unit, outdoor hot-tub
Mar 24 – 31
$76 per night
4.88 out of 5 average rating, 57 reviews
Guest favorite
Home in Adams
Mountain View Hideaway
Jan 30 – Feb 6
$104 per night
4.9 out of 5 average rating, 63 reviews
Guest favorite
Apartment in Pittsfield
Downtown Apartment A
Jan 15 – 22
$144 per night
4.91 out of 5 average rating, 66 reviews

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

110 properties are a good fit for families

Total number of reviews

6.9K 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 100 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 cottage rentals in Pittsfield?

    Pittsfield has more than 10 family-friendly cottage 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 bed and breakfast rentals in Pittsfield?

    Experience the best of Pittsfield with our bed and breakfast 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 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 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.

Destinations to explore