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Vacation rentals in Pittsfield

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

Hancock Shaker Village161 locals recommend
Berkshire Museum102 locals recommend
Big Y World Class Market80 locals recommend
Ashuwillticook Rail Trail74 locals recommend
Barrington Stage Company64 locals recommend
Colonial Theatre56 locals recommend

Other great vacation rentals in Pittsfield

Top guest favorite
Home in Wilmington
5 out of 5 average rating, 14 reviews

Spring Hiking Pet Retreat I Game RM l ChimneyHill

LynnRating, 5 stars2 months ago
Shannon’s place was perfect for our Christmas visit with our son. Clean, spacious, great location, fully stocked, and made the perfect place to host our son and his Copper Mountain colleagues for Christmas!
Top guest favorite
Home in Athens
5 out of 5 average rating, 38 reviews

Perfect home for a getaway from NYC

ScottRating, 5 stars1 month ago
Antonio and Yoon's place was perfect for our large group and dog. It's a very spacious home that is thoughtfully designed and in a lovely residential community. The beds and furniture were extremely comfortable, the backyard huge with a large patio and a fire pit. The six bedrooms, three full bathrooms, two living rooms, dining room, fully stocked kitchen, and finished basement gave our group of ten adults more than enough room to both gather together and enjoy time on our own. The location is near wonderful hikes and great restaurants and shops in Athens, Catskill, Hudson, and more. Antonio and Yoon were proactive, friendly, and clear in all communications. Highly recommended!
Top guest favorite
Home in Granby
5 out of 5 average rating, 7 reviews

Lake house retreat Granby CT

DianeRating, 5 stars2 weeks ago
We were in the area to meet our son's fiance's extended family. Nathania's home was perfect! We had 7 adults and 5 little boys ages 9, 7, 5, 2, and 2 months. There was plenty of space to spread out and enjoy the time together. The hot tub, kayaks, and foosball table were especially popular! We were able to host a family dinner with guests which was wonderful. Everything we needed for preparation was readily available. Lots of beautiful parks, playgrounds, hiking areas. Plenty to keep everyone entertained! Nathania was extremely kind, gracious, and responsive to questions. We had absolutely zero issues. So grateful for a wonderful vacation. Thank you for sharing your idyllic home with us. We hope to visit again!!!
Guest favorite
Home in Monroe
4.93 out of 5 average rating, 14 reviews

The Camp

BrendaRating, 5 stars2 months ago
We enjoyed a short ski trip to Berkshire East. M's place was comfortable, spacious and clean. The kitchen had everything we needed to cook and make coffee. They even had dog bowls and treats for our pup! Snow removal was completed early, allowing us to get out and on the slopes for the day. As M says in the description, you definitely need a vehicle with AWD or 4X4 since you are nestled in the mountains. We enjoyed the bountiful binder with history of the small town and local attractions. I would caution people with young children and older folks about the steep staircase to the 2nd floor where the bedrooms are. The 1 full bath is on the first floor so if you're like me, you need to navigate the stairs in the middle of the night. We didn't mind this since it is part of the charm of a historic building and our family of four including two teens had no problems. We enjoyed our stay and would love to return!
Top guest favorite
Home in Great Barrington
5 out of 5 average rating, 13 reviews

Great Barrington Ranch. Sleeps 10,Hot Tub, 5 acres

JuanRating, 5 stars1 month ago
We loved this airbnb! The location was perfect very close to Catamount where we went skiing. The house had plenty of space for 9 people. The best part was the host though. Alyssa’s communication is great and she was very flexible and helpful. Would definitely stay again!
Guest favorite
Home in Wilmington
4.88 out of 5 average rating, 105 reviews

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts

JamesRating, 5 stars1 week ago
Place was great! Less than 10 minutes to Mount Snow. We had fun playing ping-pong, air hokey, pool, and darts! Relaxed by the wood burning stove. Lots of rooms and beds.
Guest favorite
Home in Athens
4.91 out of 5 average rating, 11 reviews

Cozy Catskill Getaway by Hudson

PaulaRating, 5 stars1 week ago
Lovely and cozy house, perfect for families! We will be back with nicer weather! Perfect house to make you feel at home with a lot of games to keep everybody entertained
Top guest favorite
Home in Averill Park
4.96 out of 5 average rating, 159 reviews

Cozy, peaceful lake house close to Jiminy Peak

JenRating, 5 stars1 month ago
We loved our late winter stay on the lake - it was very peaceful and we had some great bird-watching opportunities. The art and special objects in the house made for a very cozy and beautiful environment. Overall, it was very comfortable and we would definitely stay again.

Quick stats about vacation rentals in Pittsfield

  • Total rentals

    230 properties

  • Nightly prices starting at

    $10 before taxes and fees

  • Total number of reviews

    8.3K reviews

  • Family-friendly rentals

    120 properties are a good fit for families

  • Pet-friendly rentals

    90 properties allow pets

  • Rentals with a pool

    20 properties have a pool

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Pittsfield?

    Yes! Work meets play with ease at over 120 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 90 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in cottage rentals in Pittsfield?

    Experience the best of Pittsfield with our cottage rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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!

  • What are the most popular amenities for House Rentals in Pittsfield?

    Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with self check-in, over 90 homes with wifi, over 40 homes with a bbq area, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do apartment rentals in Pittsfield have wifi?

    Absolutely! We offer over 80 apartment rentals with wifi in Pittsfield. Enjoy a tailored experience with all the comforts you desire.

  • 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.

  • 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.

  • Do house rentals in Pittsfield have self check-in?

    Absolutely! We offer over 40 house rentals with self check-in in Pittsfield. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly apartment rentals in Pittsfield?

    Pittsfield has more than 30 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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