Book Private Vacation Homes in Pittsfield, USA

Find your next stay with 2,200,000+ Hotels, Homes, Apartments & Villas

magnifying-glass.svgclose.svg
December 2025
Dec 2025
MonTueWedThuFriSatSun
Jan 2026
MonTueWedThuFriSatSun

Wednesday 31 December 2025 - Thursday 01 January 2026 (1 night)

calender.png
31 Dec 2025
Wednesday
calender.png
01 Jan 2026
Thursday
people.png
2 Adults - 0 Child
1 room

Pittsfield - 3 Private Vacation Homes to Choose From

Find deals where other travellers are staying
See map view

Hotel stars

best price
Best Price Guarantee

We guarantee we won't be beaten on price. If you find a cheaper hotel deal on another website after you book with us, we’ll refund the difference!

See the latest prices and deals by choosing your dates. Choose dates

Sweet Life - GetAway

64 Dove Drive, Pittsfield, USA - See map
Free WiFiParking availableEntertainmentAmenities

The Getaway 4 Bedroom Home

63 Tozier Hill Road, Pittsfield, USA - See map
Parking availableDining servicesEntertainmentAmenities

Sweet Life in Pittsfield

64 Dove Drive, Pittsfield, USA - See map
Free WiFiParking availableSpaAmenities
promotion

2% giveback on bookings

Create an account or login to unlock these rewards

See all private vacation homes in Pittsfield

Top Picks for Private Vacation Homes in Pittsfield

Try one of these popular top-rated private vacation homes in Pittsfield
Loading...

Explore Pittsfield

Discover new destinations in Pittsfield and find your next stay!
Loading...

Search by Holiday Style

Discover your ideal stay: explore pet-friendly homes, eco retreats, luxury accommodations, and more
Loading...

FAQs About Private Vacation Homes in Pittsfield

What's the best place to stay in Pittsfield,Massachusetts, USA?
plus-blue.svg
The best place to stay in Pittsfield is the Hilton Garden Inn due to its comfort and proximity to local attractions.
What's the best place to stay on a budget in Pittsfield,Massachusetts, USA?
plus-blue.svg
The Berkshire Inn offers budget-friendly rates and comforting amenities.
What are some family-friendly private-vacation-homes in Pittsfield,Massachusetts, USA?
plus-blue.svg
Spacious homes like the 'Berkshire Family Retreat' and 'Lakefront Paradise' are great for families.
What's the best accommodation for a romantic getaway to Pittsfield,Massachusetts, USA?
plus-blue.svg
The 'Cozy Cottage' offers a romantic, intimate setting.
What's the best accommodation for an all-inclusive stay in Pittsfield,Massachusetts, USA?
plus-blue.svg
The Courtyard Marriott offers all-inclusive packages.
Where can I find pet-friendly private-vacation-homes in Pittsfield,Massachusetts, USA?
plus-blue.svg
Try 'The Pines' or 'Lakefront Paradise', both are pet-friendly.
What's the best boutique private-vacation-homes in Pittsfield,Massachusetts, USA?
plus-blue.svg
'The Artist's Loft' provides a unique, boutique experience.
What's the best spa private-vacation-homes in Pittsfield,Massachusetts, USA?
plus-blue.svg
'Berkshire Spa Getaway' features its own private spa facilities.
What private-vacation-homes in Pittsfield,Massachusetts, USA have nice views?
plus-blue.svg
Homes like 'Lakefront Paradise' or 'Boulder Terrace' offer beautiful views.
Do private-vacation-homes in Pittsfield,Massachusetts, USA offer airport transportation services?
plus-blue.svg
While some do, it's not standard. Make sure to check with each individual property.
Destination

Discovering Pittsfield's Coastal Charm and Urban Wonders

Discover what to do and what to see in Pittsfield

Escape to the picturesque town of Pittsfield, Massachusetts, and experience the charm of this vibrant destination. Discover our handpicked selection of private vacation homes on Travala.com, offering the perfect retreat for your next getaway. Nestled in the heart of the Berkshires, Pittsfield boasts a wealth of natural beauty and cultural attractions. Immerse yourself in the stunning landscapes as you explore the nearby mountains, lakes, and forests. Embrace the outdoors with hiking, biking, or skiing adventures, or simply relax and soak in the tranquility of your surroundings. Make time to visit the renowned landmarks that make Pittsfield truly unique. Delve into the town's rich history at the Berkshire Museum, showcasing a fascinating collection of art, natural history, and science exhibits. Admire the iconic Colonial Theatre, a historic venue that showcases a range of performances from Broadway shows to live music concerts. For art enthusiasts, Pittsfield is a haven. Explore the vibrant local art scene at the Berkshire Museum of Art and the Lichtenstein Center for the Arts, where you can view captivating exhibitions and engage with local artists. At Travala.com, we believe in offering convenience and flexibility for our guests. We offer multiple payment options, including credit cards, debit cards, and even cryptocurrencies like Bitcoin. Book your private vacation home with ease and embark on a memorable journey to Pittsfield. Indulge in the charm and allure of Pittsfield, Massachusetts with our selection of private vacation homes on Travala.com. Immerse yourself in nature, explore cultural landmarks, and create lasting memories in this captivating destination. Book your stay today and embark on a truly unforgettable experience.

Read more

Explore Our Travel Guides

  • Travel Planning
  • CRYPTO
  • Travel Destination
  • Accommodation Guides
  • Travel Trends
  • News

FAQs

      More Ways to Explore Pittsfield, the USA

      See what else the USA has to offer
      Type of Accommodation in Pittsfield, the USA
      Budget Options in Pittsfield, the USA

      Customer Reviews
      What our customers say

      Crypto-friendly Bookings

      Your money’s good here.

      Loading...

      We pride ourselves on being the leading crypto-native travel platform. Pay for your travel anywhere in the world seamlessly using 100+ cryptocurrencies or traditional payments.