House holiday rentals in Woodstock

We really enjoyed our stay at this super cute Airbnb! The location was perfect — just a quick drive to everywhere we wanted to go, which made exploring the area super convenient. The space itself was clean, cozy, and had such a charming vibe. One thing to note is that there’s no AC, which I didn’t realize ahead of time. It wasn’t a dealbreaker by any means, but as a cold sleeper, it was a bit warm for me in June — just something to keep in mind depending on the season. Overall, it was a lovely place and a great spot for a getaway!

Ashley was super friendly and responsive and her place was as described with everything I need and more to make me feel right at home. Would love to stay here again. Thank you so much for letting us stay at your beautiful place!

We enjoyed our stay. we felt at home. very spacious and cozy. this house has everything you need for your stay. Very close to Rutland. The fresh baked apple pie was a bonus. It was so delicious. Everything was perfect for us! Thank you! We will definitely be back again!

Perfect place for a family ski trip. The only negative feedback I heard was that the house was so nice, my father in law had nothing to complain about.

Great location and lots of space. We were able to ski in/out (look for "Cliff's Road" sign when skiing back) fairly easily, which was nice. Would definitely stay here again. Thanks!

Kat’s house on Dana road was the perfect place for our vacation to Vermont. Our family appreciated the clear instructions, helpful hints, and well thought out amenities. We really liked the Whisper Hill products in the bathrooms and made sure we went to the store in Quechee to buy some of the lotion before we left. We have stayed at a lot of AirBnB’s, but the house on Dana road was the most well equipped out of all of our stays!

My family and I truly enjoyed our time spent at the farmhouse. Everything was as expected from the listing. The pictures do not do justice for the property. It's beautiful and well maintained. The pool was nice, warm, and clean. There are yard games readily available and a nice fire pit area. Brin and Maria are super responsive and left very detailed instructions on the property for you. Everything you need is there minus food, which is a 12-minute drive towards a few different grocery stores. The hill is so fun to roll down, too! Thank you so much!

Staying here is always a joy for the entire family! It has become an annual tradition that we all look forward to in winter. Thank you for being so accommodating with our schedule and a special thanks to Mitchell for going the extra mile to snow blow a waking path for me and the dogs to keep our daily routine of visiting the horses, after the last storm brought over 13” of snow. P.S. the new stove/oven is amazing!! 🤩

We loved our stay at Stacy’s pretty little cottage. It was really spacious. We liked the creativity and quirkiness of the space and we had everything we needed for a family of four. Woodstock and Quechee are nearby and we enjoyed the fall foliage, delicious local food, apple orchards and the amazing local pies. We would definitely stay there again.

We loved our stay at David’s cottage. He is an incredibly responsive host. The location of the cottage is the perfect location between Woodstock and Killington. Would return again!

The log cabin is very comfortable with great flow. Loved the sunroom and upstairs den. Heated floors in bathrooms and sunroom were great touches. Not conventional decor: maximally furnished with an interesting blend of western, contemporary abstract art and figurative paintings and knick- knacks. We thought it fun and loved our stay.

We had a great stay! The house was well-appointed and comfortable. We especially loved the covered porch and beautiful view. It was a great home base for exploring the area, including several nearby hiking trails, Woodstock and Quechee (about a half hour away), and Brattleboro (less than an hour away). Ab was a fantastic host. He was proactive with communication and even checked in with us to make sure we had power after some strong thunderstorms that had moved through the area.

The space was just as described. The view of the mountains is beautiful, and the house sits far enough above the road that there's no sounds of traffic. It felt secluded and peaceful, with all the amenities one would need.

Spend a long weekend with 2 other couples at The Brook House, we had a wonderful time. The house was beautiful, just as described. The house was super clean and neat from top to bottom. Plus the bedding was comfy! The kichen and grill are a cooks delight! We enjoyed making meals on the grill and in the kitchen. The decor of the place was so cool, Jeff has great taste! Jeff was highly responsive to all of our inquires from the get go. Check in was simple, the instructions clear. I have to note the landscaping, it was so pretty. We spend much time sitting outside and enjoying the flower gardens and sound of the brook. We would definitely return and highly recommend this house!

Ashley was incredibly helpful, kind, and responsive. Highly recommend!

This was our 3rd time staying at Ashley and Charlie’s place! We love it there. Location is perfect and the fenced in yard is wonderful. Our two kids and two pups love to run around and it’s a nice place to sit and relax. House is clean, organized and feels like home. We look forward to staying again!

We came here with our infant and had the perfect little trip. Amazing house — just as pictured, beautiful view, super clean, amenities, sauna. And awesome location— the house is very quiet and rural, but it’s close to a lot of spots— we went to breakfast at Barnard General Store (best pancakes of my life x100), went into Woodstock to walk around and eat, went to Longtrail Brewery for Friday night trivia, quechee gorge for a small but pretty hike, Worthy Burger for food and cocktails, and silver lake syrups to learn about and buy maple syrups (including taste tests) … lots to do. We had bad weather all weekend; if it had been good weather, it would’ve been even better with hiking and stargazing and outdoor fire. I don’t like to go to Airbnbs twice, but this place is high on my list to visit again- either in the summer or winter. Jenny is a very responsive and helpful host. Overall one of my best Airbnb experiences.

We required a venue for the wedding party, and Maura’s residence was ideal. The property was well-stocked, with sufficient supplies for the kitchen, bathrooms, and bedrooms. Notably, ample firewood was available for the fire pit. The beds and furniture were impeccably clean and comfortable. It is evident that Maura takes meticulous care of their property and prides themselves on providing a clean and hassle-free environment. .

Kevin and Emily's home offers a cozy launching point for adventures around Woodstock and the upper valley area, with a setting that is incredibly peaceful and picturesque. Kevin was very clear with directions and extremely responsive while we were staying at the house. He also generously agreed to a delayed checkout, so my daughter and her friend could enjoy a last dose of winter fun before our departure. The house had everything we needed, including two sledding saucers for snow play, and a gas stove to warm up next to after coming in from the cold. One small detail to note--the lower bunk bed has a low/confined ceiling that can be tricky for taller kiddos. Overall, we had a lovely stay and would definitely come back to explore the trails in another season!

We had a wonderful stay! We would absolutely recommend staying here. The house worked well for myself, husband and 4 year old son. There were even a few toys he was able to play with, in addition to a large lawn and a stream near by! There are also very thoughtful touches with amenities to make traveling and staying somewhere more convenient and comfortable.

This house was wonderful. Had so many thoughtful amenities, especially for families with children. Lots of kids toys, books, games. There was plenty of sleeping space and lounging space. Especially loved the big kitchen table. We really appreciated that the kitchen was stocked with some helpful pantry items and also had plenty of cookware. It made cooking for 3 large families easy and enjoyable. We will definitely be back. thank you!

Carl & Poppy were fantastic hosts. Very responsive, and kind! The house was perfect for two people, and the hot tub was an added bonus every night when we got back to the house. Everything you need for a nice stay. The traffic was a little bit loud trying to talk on the porch throughout the day, but we made the best of it. All in all, highly recommend!

Absolutely loved staying here for our anniversary. It had everything we needed to unwind and relax. The views were beautiful from just about every spot on the property and every detail was included to make the stay feel more at home.

Megan's place was beautiful! In the past we have spent several summers in Woodstock and this year we decided to try something different and we were so glad we did! While we were a 20-30 minute ride from Woodstock, we enjoyed the ride, seeing people on horses and bicycles making their way on the hilly, tree covered roads and seeing the beautiful farmland on either side of us. The yard is so pretty and each morning it looked a little different, depending on the weather so I was out there with my camera capturing as the fog lifted or as the large trees looked in the sun-filled sky. The house is very comfortable with two areas for sitting on couches and though we were only two people, with a dog, we enjoyed that we could each take a room for reading and then come together for a movie in the evening. The kitchen was well-stocked and we enjoyed our meals in the dining room using the wooden dining table. Communication with Megan and her husband was wonderful - they are great hosts! Enjoy.