Holiday rentals with outdoor seating in Pittsfield

Very nice place easy access to routes 4 and 100 with plenty of things to do

I have been booking a ski trip with my friends for 10 years now, everyone said this was by far the best house we’ve stayed at and I agree! Location, comfort, and price were all perfect! We will absolutely be back!

The Bow house was a beautiful place and Jen was incredibly hospitable and responsive. This is an amazing place to come and get away from the noise. Everything was so clean and cozy. Would definitely come again!

The barnbrook house was lovely, private and rustic. It had everything our family needed as a base to explore VT/NH. The mountain views are sublime and the house is tucked away offering a lot of privacy. As far as amenities, we loved the toy chest, darts board, and den. There’s plenty of space for a family and Dana stocked up the kitchen with coffee and tea. If you need to be in Hanover for events, this location is a 45 minute drive so keep that in mind when planning.

We loved our stay here!! It was the perfect getaway for a long weekend. The property is beautiful and private but close to anything that you might need. The kitchen was super well stocked, beds were comfy, and we really appreciated the firewood supply. Nikki & Topher were great hosts - extremely responsive to all questions we had and proactive about check in/check out instructions. Would definitely come back!

We had a great time at David's place. The kitchen was well stocked, plenty of firewood, and the hot tub was ready to go. The house was very clean. All the bedrooms had plenty of linens, and extra blankets. We would definitely stay at David's again!

We had an amazing stay! The place is in a fantastic location—perfect for exploring Woodstock or Killington—and it was super cozy, clean, and well-equipped. Robyn and Trevor were outstanding hosts, always quick to respond and incredibly helpful. The easy communication made the entire experience seamless and stress-free. Highly recommended!

The space was fantastic for our two little families with easy access to the local Slate Valley Trails. Lots of wonderful and attentive touches to make our stay homey welcoming. Hope to return again soon!

Our second stay here was great, river was a little higher but we wanted a peaceful weekend with friends and dogs. Apartment was warm given the unseasonable cold weather and we had all the amenities we needed even dog towels for wet pups. Did not see the host during our stay but she was in contact as needed.

Small but has a fully equipped kitchen, other than the only sink is in the bathroom. The sink is big and it worked fine. The park is 1/2 block away and town is 2 blocks. Comfortable bed and quiet at night. Good restaurants and unique shops in town. Lots of nature trails close by. Be mindful of having the key it could be easy to get locked out. We enjoyed our time in the apartment and definitely would recommend it to anyone who wants to visit Bristol. Thanks for sharing your place with us.

We had the most fantastic stay with Sheila and Jeremy! The home was spotless and beautifully decorated. Sheila was a proactive and responsive communicator. But what stood out to us more than anything were the various thoughtful touches provided during our stay. We arrived late, after a long drive, and Sheila and Jeremy were there to meet us in person and help carry our bags inside. They had fresh muffins waiting and even left some snacks (cheese, crackers, grapes) in the fridge in case we hadn’t eaten dinner. They also provided coffee, tea, milk, honey, which was great in the mornings, and we so appreciated having access to the washer & dryer to do some laundry. Overall, we can’t say enough good things about our stay and we hope to return!

Camilla is a wonderful host and a gem of a person. She made my almost month of stay at her beautiful and inviting studio, extremely comfortable and delightful. The location is perfect as it is walkable to everything Montpelier has to offer but also private and peaceful. Highly recommend staying here if you visit.

Loved staying with Sandra and Jason! They are great hosts and did a great job on the Airbnb. We knew there were going to be mosquitoes, but we didn’t know that there were going to be so many, I would advise bringing bug spray. They let us use their kayaks which was an awesome experience. 10/10 would stay again.

Loved staying here. Apartment was great, comfortable and clean and spacious. Andrew and Kate were great hosts, letting us use the playset outside with our toddler. Porch view was wonderful, looking out towards some hills and over a field that had various critters all day and fireflies at night!

Amazing and great hosts! Very clean. Perfect for our ski team. we loved enough bed and beautiful views. We will definitely be back. ♡♡♡♡♡♡♡

for being in the city area it was pretty quiet. place is clean. good location would stay again

Great spot right on the mountain. We will be back next season.

This was our second time staying at Caitlyn’s condo in Killington, we chose it again for a reason !! The vibe of the condo is super relaxing, the decor is thoughtful and cool. The fire place makes coming back after a day on the slopes so cozy! We love coming to Killington and this condo is so close to the snowshed lot, it’s perfect!

Great place! We enjoyed our stay so much that we extended it an extra day. Hosts made it super easy to extend.

We had an amazing stay at this place! The location was perfect—just a short walk to all the incredible relaxation amenities like the pool, steam room, and sauna, which made our trip feel like a true escape. Going for a walk while taking in the views of the mountains were absolutely stunning and made every morning feel special. The unit itself was spotless and had everything we needed for a comfortable, short stay. The kitchen was well-stocked, the bed was cozy, and everything felt thoughtfully arranged. It was the perfect home base for exploring Killington and unwinding after a day of adventure. Would absolutely recommend and may come back during the Peak of the Snow Sport Season!

My family and I had an awesome stay in Tina's apartment. We took full advantage of the outdoor pool and the indoor spa space, which were both fantastic. The unit was a clean, cozy and comfortable place to return to at the end of busy days. Tina was an exceptional host - one of the most responsive/helpful experiences I've had with an Airbnb host. We would definitely stay here again!

We loved it. Although it’s not the newest or fanciest condo the location can’t be better right at the Clocktower Base. Our family of for had an amazing time snowboarding and exploring the area. Great restaurants close by and we will definitely be back next year.

Very comfortable stay - convenient to ski wither Sugarbush or Mad River. Philip sent specific instructions for turning the heat up on arrival. It took a little while to warm up, but individual thermostats in LR and BR worked nicely. Local recommendations for restaurants and such were spot on.

Great home near the mountain, exactly how described and shown in pictures. We had a wonderful stay.