Vacation rentals in Pittsfield

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Popular amenities for Pittsfield vacation rentals

Stay near Pittsfield's top sights

Clear River Tavern23 locals recommend
Original General Store20 locals recommend
Vermont River Tubing16 locals recommend
Green Mountain Trails16 locals recommend
The Backroom14 locals recommend
White River Golf Course11 locals recommend

Other great vacation rentals in Pittsfield

Guest favourite
Home in Wells
5 out of 5 average rating, 12 reviews

Breathtaking Lakeside Retreat!

BrianRating, 5 stars2 months ago
Second year renting. Great place, definitely would recommend. Hope to return next year. Brooke is a fantastic host. Thank you
Guest favourite
Condo in Killington
4.75 out of 5 average rating, 92 reviews

Still 89 Trails Open, Low, Low Rates

RyanRating, 5 stars1 month ago
Convenient to the slopes via the shuttle that picks up out front. Able to walk to a good restaurant, Still on the Mountain. Place is comfortable and has everything we needed for a weekend skiing.
Top guest favourite
Home in Chittenden
5 out of 5 average rating, 8 reviews

Modern Retreat next to Mountain Top Inn,Killington

MaddyRating, 5 stars2 months ago
I couldn't recommend this place more! My cousins and I had a great time and Uli is super attentive. The hot tub has a great view of the lake, it was also salt water which I love. The space was extremely cozy and exactly what we needed. We snowboarded pico and killington and it was about a 25-30 minute ride. We will for sure be back! Thank you guys so much!
Top guest favourite
Home in Plymouth
5 out of 5 average rating, 16 reviews

Luxury Modern Cabin near Okemo & Killington

TariQRating, 5 stars1 month ago
Stephanie was an Incredible host! The listing matched her description and the property looked even better upon checking in. Stephanie maintains this property really well and I couldn’t have felt any more at home. The home was clean and had a perfect cozy feeling to it. In addition, this was really close to the mountain, which made the getaway even better. I enjoyed the privacy and waking up to a nice snow dusting before my trip to the mountain. I highly suggested staying at Stephanie’s property if you’re looking for a quick getaway. I certainly will be looking to book again soon. Thank you Stephanie!
Top guest favourite
Home in Warren
4.97 out of 5 average rating, 39 reviews

Private Home with Hot Tub 1 mile from Sugarbush

ThomasRating, 5 stars1 month ago
We had an amazing stay at Don’s place. The location was perfect, allowing us to enjoy four great days of skiing. Don was a fantastic host, making everything easy from start to finish. The house was ideal for our extended family of eight, offering plenty of space and comfort. If you’re looking for a spacious, well-located home near Sugarbush, I highly recommend staying here!
Guest favourite
Home in Newport
4.93 out of 5 average rating, 57 reviews

Crescent Lake home swim, golf and hike

SaraRating, 5 stars2 months ago
We loved the home. Perfect for our ski vacation to Sunapee and Okemo! It was one of our favorite Airbnb’s. So cozy, great location, great atmosphere, great decorating, etc. We just felt right at home from a minute. We walked in the door Beds comfortable. The upstairs is great if you have a few kids who just want to crash on a bunch of different beds. Laurie, who we mostly communicated with, was fantastic. So nice and so easy to get in touch with if we needed her for anything. Thanks for a great day! Hope to come back someday.
Guest favourite
Condo in Killington
4.96 out of 5 average rating, 27 reviews

Modern Dog-Friendly/Fireplace/Spa/Pool/Tennis/AC

ChrisRating, 5 stars3 weeks ago
What a great place. It was very enjoyable for the whole family. There were plenty of board games, and an arcade game (packman along with many other old game's to choose from). It was sleek, it was spotless and had everything we needed. We loved the area and spa. Thanks and we will hopefully see your great place again soon.
Superhost
Tiny homes in Fort Edward
4.86 out of 5 average rating, 58 reviews

Tiny Home In Paradise “The Big Dipper”

AlannaRating, 5 stars10 months ago
If you’re looking for a quiet place to get away for the weekend, look no further!! Pete was so nice and incredibly responsive. My fiancée and I will definitely be staying here again!

Quick stats about vacation rentals in Pittsfield

  • Total rentals

    80 properties

  • Nightly prices starting at

    $166 CAD before taxes and fees

  • Total number of reviews

    3.1K reviews

  • Family-friendly rentals

    60 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Rutland County
  5. Pittsfield