Holiday rentals with outdoor seating in Pittsfield

A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

Thank you to Leif and the family for a great stay! Leif was a fabulous host, being very helpful and responsive. His wife was also very nice and shoveled out the walk way for us. The place was just as described in the listing. Comfy beds with easy access to the ski way. Thanks Leif!

We enjoyed our stay immensely! We visit Rutland often and will continue to stay here as long as it is available! Everything was better than anticipated!

Such a beautiful home! Great kitchen for cooking and cozy living room perfect for watching movies. Enjoyed our stay very much.

We have the loveliest time and can’t wait to return. Thank you for being so helpful and responsive

I thoroughly enjoyed my short weekend stay. The home is immaculate and Lynn has thought of everything that makes an Airbnb comfortable including a well-equipped kitchen, comfortable furniture, logical lighting (so often very poor in many places) and lots of little things that you don't realize are important until they aren't there. The house is very secluded with two lovely porches and a dining deck. Lynn's communication is excellent. This is one of the best Airbnb's that I have stayed at.

Cute Vermont farmhouse that had everything that you needed. We enjoyed Cooking inn and hanging out in the living with the fireplace. The hot tub was so much fun after a cold day on the mountains. There is a cute little coffee shop and super market only 10 minutes away.

A very comfortable and peaceful getaway. Everything we possibly needed was available. And, Alan is incredibly responsive.

Perfect location to headquarter at while exploring all the things central Vermont has to offer. Very private and quiet.

This rental was perfect for our family’s overnight ski trip to Okemo. We have two teenaged sons who shared a bedroom. The kitchen had everything we needed to cook breakfast and (most importantly) to meet the AM caffeine needs. The rental was approximately 10 minutes away from Okemo, which was the best part for us. Already planning next February’s ski trip!

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!

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

Andrew’s place was exactly as described. Just far enough out of of the middle of Middlebury to be completely peaceful, but a very quick drive to town. The space was clean, spacious and had a great kitchen. The view off of the back deck was fabulous. I’d definitely stay there again.

My daughter and I had a great time. We were able to bike several times straight from the house, and the town had everything we needed for a local run, food shopping, and restaurants. It was a perfect little getaway!!

Very friendly host and location is in a quiet part of town. it felt very private as well. A++

Dick and Dorothy are some of the most lovely, hospitable folks we have ever met and we feel so lucky to have gotten to know them through our extended stays at their apartment for the the last 5 winters. Hancock is a truly special community and the apartment is an excellent choice for anyone looking to visit the area. It is conveniently located, well-stocked, and delightfully quaint. We are already excited to return!

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!

This space was perfect for our family. With walking distance to the entrance of the slopes, this location was ideal for our ski getaway. I appreciated the small touches that made this experience feel luxurious, the provided coffee, wine, wood for the usable fire place. The beds were comfortable and the space was spacious. We would definitely visit Jim’s place again!

Extremely nice cabin, very recently renovated. The owner has a keen eye for organization, everything is neatly placed where it should be. Linens are clean, beds were super comfortable. Amazing stay, thank you Cathy

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!

Very clean, cozy and spacious place to stay. Well-equipped kitchen, clean bed sheets and towels. Very easy access to Killington ski resort Ramshead Base. Tina is a great host!! I would recommend this apartment!

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.

This was our first visit to SnowCub at The Woods and it was comfortable and well-equipped. Holly and Dan were great hosts - responsive, thoughtful (loved the greeting gifts), and easy to work with. I already booked another trip for June!

Great location for pico mountain. The ski on ski off was pretty easy to find and nicely located. The location is slightly less ideal for killington, as you need to take a shuttle that has multiple stops. We also ended up on a bigger bus to take us back from Killington and the drop off was on the main road, which was a bit difficult to walk on in our snow gear. Overall, nice apartment and perfect for my group of friends.