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 favorite
A wooden railing frames the outdoor balcony, offering views of the calm lake. Sunlight glimmers on the water's surface, with green hills visible in the background. A few boats are moored nearby, and the scene conveys a serene outdoor environment.
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 favorite
An outdoor pool is surrounded by lounge chairs and red umbrellas. Lush green trees frame the space, creating a serene environment. A small poolside shed is visible, adding functionality to the area.
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 favorite
A warm hot tub is presented against a snowy landscape, surrounded by trees bare of leaves. The distant view of the reservoir is framed by the serene white of winter, inviting relaxation and tranquility.
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!
Guest favorite
A spacious deck is presented with a wooden table and several chairs, overlooking a verdant landscape. The scene is complemented by a backdrop of rolling hills under a partly cloudy sky, showcasing the natural beauty of the surrounding area.
Home in Dorset
4.93 out of 5 average rating, 44 reviews

Mountain View Getaway

ChristinaRating, 5 stars1 week ago
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!
Top guest favorite
A modern home is set amidst natural greenery, featuring a wood-paneled exterior. The structure showcases multiple oversized windows on each floor, allowing for ample light. Surrounding grass and trees create a serene environment, enhancing the sense of privacy and tranquility.
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 favorite
A spacious hot tub emits a soft blue glow in the dark, surrounded by mist. The area is accented with a wooden deck, and a staircase provides access to the tub. Soft lighting enhances the peaceful ambiance of the outdoor space.
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 favorite
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 favorite
An indoor pool area features large windows that bring in natural light, showcasing winter scenery outside. Comfortable lounge chairs and a table with an umbrella are arranged around the pool, creating a serene space for relaxation.
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.

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.

Destinations to explore

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  5. Pittsfield