
Vacation rentals in Pittsfield
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Top-rated vacation rentals in Pittsfield
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Vacation rentals for every style
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Popular amenities for Pittsfield vacation rentals
Other great vacation rentals in Pittsfield

Breathtaking Lakeside Retreat!
Second year renting. Great place, definitely would recommend. Hope to return next year. Brooke is a fantastic host. Thank you

Still 89 Trails Open, Low, Low Rates
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.

Modern Retreat next to Mountain Top Inn,Killington
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!

Mountain View Getaway
Beautiful home in the mountains! We enjoyed the breathtaking view and loved that it was only about 15 minutes from downtown Manchester. Great get away!

Luxury Modern Cabin near Okemo & Killington
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!

Private Home with Hot Tub 1 mile from Sugarbush
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!

Crescent Lake home swim, golf and hike
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.

Modern Dog-Friendly/Fireplace/Spa/Pool/Tennis/AC
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.
Quick stats about vacation rentals in Pittsfield
Total rentals
80 properties
Nightly prices starting at
$120 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
Frequently Asked Questions
Do chalet rentals in Pittsfield have a kitchen?
Absolutely! We offer over 10 chalet rentals with a kitchen in Pittsfield. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Pittsfield have wifi?
Absolutely! We offer over 40 house rentals with wifi in Pittsfield. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Pittsfield?
Yes! Work meets play with ease at over 30 vacation rentals in Pittsfield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do hotel rentals in Pittsfield have free parking?
Absolutely! We offer over 10 hotel rentals with free parking in Pittsfield. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Chalet Rentals in Pittsfield?
Enhance your stay in our Chalet Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Pittsfield?
Four-legged friends are welcome in Pittsfield. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Pittsfield?
Pittsfield has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Pittsfield have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Pittsfield. Enjoy a tailored experience with all the comforts you desire.
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- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Northeast Slopes Ski Tow
- Ekwanok Country Club
- Country Club of Vermont
- Baker Hill Golf Club
- Dartmouth Skiway
- Hildene, The Lincoln Family Home
- Adirondack Extreme Adventure Course
- Autumn Mountain Winery
- Cozy Cottages & Otter Valley Winery
- Bromley Mountain Ski Resort
- Lincoln Peak Vineyard
- Vermont National Country Club
- Dorset Field Club
- Killington Adventure Center
- Fox Run Golf Club
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