Vacation rentals with a fireplace in Pittsfield

Steal of a deal for this place. Perfect for any couple or family looking to do a vermont ski vacation. Has all the amenities you need, it’s super spacious, it’s right by town, and it’s a short drive to stratton or bromley. Easy 5 stars.

We checked in to Kalyn’s house just before a storm gave us 15” of fresh snow. What a great place to get cozy in the winter! The house is remarkably clean given its rustic charm. The beds and bedding were all amazing. The record collection and fireplace set the mood for cooking and enjoying a meal. Our two sons and sheepdog Denver loved it too!

This place is a gem! Large space but felt intimate and cozy. The fireplaces are great, the deck looked inviting but we had so much snow, we spent most of our time on the slopes. Amazing art work throughout, well stocked kitchen, and lots of light! Great space.

This cabin is the perfect VT log cabin retreat. My family and I stayed three nights this past weekend and loved it the minute we walked in. Rustic but with. modern appliances and amenities and tons of charm. The giant stone fireplace was not only beautiful but really helped heat the space well. As in any log cabin, there are some drafty spots, but the heat works well and there are lots of cozy blankets if you catch a draft. There is no heat upstairs and I was a bit worried about that as it was in the teens when we arrived, but the heat from downstairs does help upstairs and there are tons of blankets in each room. Great sleeping conditions! The house was stocked with all the basics and any items you may have forgotten. The whole cabin was spotless and well maintained. Surrounded by lots of woods it is a very peaceful spot and a convenient drive to Sugarbush. Stephen was very responsive and friendly and accommodated us when we needed a later check out time.

Beautiful property in a very private, peaceful setting but still close to local amenities and rt. 89 & 91. We were very happy with the home and the host. Everything was as advertised and it was a very easy process. We would not hesitate to come back and recommend this property to others.

Absolutely stunning setting and view - so secluded and just incredible views from every window. Great size for family of 8 with enough space for everyone to relax

This house is awesome. Kitchen and bathrooms are amazing. Beds are extremely comfortable. And the back deck with the hot tub and fire place is perfect for post ski relaxation. Sarah is extremely friendly and responsive. She answered all of my questions instantly. The kitchen has pretty much everything you could need, except spices. Way more than most AirBnb rentals. The knives and cook wear were quality as well. Lots of attention to detail. 100% would recommend and will be staying here again next season when I ski Okemo.

This home is much larger than it appears in the photos. It's beautiful and cozy (but not "small cozy"). My group skied Bromley, Stratton, Okemo and Magic, which were all within 25 mins or less. (Bromley is 5 mins). This home felt large enough for multiple family's with or without children. It is well stocked with everything you would need for cooking, laundry ect. A minor issue was addressed nearly immediately. The owner is very responsive and accommodating. I would highly recommend this place and I look forward to visiting it again.

Great place to stay for skiing Sugarbush or Mad River Glen, convenient to restaurants and shops. Very quiet setting, just be prepared for a little bit of non-paved road to climb to access it. The apartment felt more spacious and open than I expected, and accommodated 3 adults quite comfortably. Wax bench was a nice bonus for us skiers!

Alex’s place was easy to find and access, and very conveniently located. Super cute and cozy apartment. Alex was helpful and friendly when we needed to message and got back right away.

This was our second stay here and we do love it very much and will continue to return as often as possible.

Amazing location! Sabrina’s place was super cozy and very clean! We would definitely stay again.

It was the perfect place to crash and enjoy a 2 night stay for our Ski trip to Killington! Loved the Mountain View’s surrounding, just wish it was kayaking season cause the offer to use the kayaks was cool haha! The design of the bathroom in the bedroom was unique but worked fairly well. Overall enjoyed and felt comfortable during our stay. Keep the heater on high since there’s no doors the air flow is pretty big during the cold nights!

The best option for 4 or less people near Middlebury VT. As a previous Vermonter for 3 years, I love the coziness and all the artifacts inside - all seemed very authentic to a Vermonters lifestyle. The hosts are super nice, very friendly, and proactive in providing instructions. The kitchen is especially well-equipped with everything we needed to cook for 4 people, which stands out from all the Airbnbs I’ve previously stayed. We come to VT quite often and it’s disheartening that this is the first time of us finding out about Docs place… Will definitely comeback!

Can't say enough! Steve was quick to have information and respond. His knowledge of the area is massive and he knows all the great spots to go. Their place was perfect and everything you'd expect from the pictures and description. During our stay we got a large ice storm. Some locals called it the worst ice storm since 1996. Steve was texting me throughout the storm to make sure we were ok and had power and internet. He asked if there was anything he could do for us... And he was located hours away.. Steve and LA went above and beyond in so many ways.. Their place will be the first place I look to stay on return trips!

Oliver is a great host, great communication. I stayed at his place for multiple weeks and it was amazing.

We had a wonderful time and felt right at home!! Her place is SPOTLESS and cozy. Simone’s instructions to get there were perfect. Everything is well labeled (like which switches do what), USB ports on bedroom lamps., binder with check in/check out info. Couch is 10/10 for post-ski nap, beds and linens are super comfortable. Kitchen items look brand new. Shower pressure is also 10/10 There is a shuttle that takes you to the resort with a stop in this neighborhood (5-10 min walk), but uphill so with kids and ski gear we drove to resort each day (2-3 min drive). The houses in the neighborhood are spaced out so you don’t feel like you are right on top of someone but also aren’t completely secluded in the wilderness. We stayed Presidents’ Day weekend and skied Lincoln Peak. The lift lines moved quickly and didn’t feel overly crowded. This rental was priced higher than other rentals we considered, but based on pristine condition and ease of our stay it was worth it!!!

This was such an incredible place to stay! The whole mansion is absolutely stunning, the surroundings and views are beautiful. However, what made this stay truly special was the incredible kindness and hospitality of the host. This was a wonderful experience and we are all looking forward to our next stay!

This was perfect for my son and I to relax in over a weekend at Pico. Everything was clean, comfortable, and we loved the fireplace as an added touch. Convenience and location were perfect; walk right out the front door and you're skiing with the buzz of the lodge right there - true ski in and out. We will definitely stay here again, for longer next time hopefully!

Very close to ski trails, the cleaning crew team did an excellent job, and really easy to work with the Killington team.

Such a great deal considering the price and amenities. The location was quite a drive from our destination but it was close to other places like Okemo and Woodstock. Beautiful surroundings. A warm full size pool in the winter time is unbeatable. Place was clean when we arrived. The building was quiet and peaceful. No issues with noise nor difficulty with checking in.

Our stay at the house was amazing! Place is very spacious so our guests were very comfortable! Plenty rooms and beds to sleep in. Kitchen is stocked up. There is everything you need ti make meals. We absolutely loved it!! Our group had people whi ski and hike . Everyone had plenty to do!! Definitely recommend that place! If we ever go back to Vermont we’ll stay there for sure!! Thank you so much for having us!

What a great condo in the best location! Unbeatable for the price. The condo was spotless, and had every amenity as described. Plenty of towels, soaps, kitchen necessities. Beds were comfortable! We really felt right at home. And the fire place was so nice! We’d definitely recommend this for a great weekend get away!

Great stay, lots of room. Front desk was super friendly.