Stay At Jimmy's

Jimmy and his staff went out of their way to make our stay wonderful! They even dug our car out after we got 8-10 inches of snow! We didn’t even need to ask. Also, the shower was amazing!!

We loved our stay Jimmy’s! This B&B is ideally located very close to Woodstock downtown, our room was funky and cozy and we loved the snacks! Jimmy and John are wonderful hosts, I highly recommend.

Our stay at Stay at Jimmy’s was absolutely wonderful. The room was beautifully well-appointed with thoughtful touches throughout, and the bed was incredibly comfortable — truly one of the best nights of sleep we’ve had while traveling. We loved the attention to detail, from the cozy setup to the yummy snacks that made us feel instantly at home. And the owner on site was genuinely kind and helpful, offering great local insight and making sure everything was perfect. A lovely place to stay — comfortable, welcoming, and clearly run with care. We’d happily return!

We highly recommend Stay at Jimmy’s! My wife and I loved bed and the room. It is spacious and really nicely designed. The numerous muffins and croissants and Peet’s coffee in our room for breakfast were delicious. A short walk to all the activities in the center of Woodstock. We’ll be back!!

Beautifully appointed rooms, yummy snacks and pastries, a delightful host. All located walking distance to town. We will be back!

Our Stay At Jimmy’s experience was great! The service was excellent, the suite was spotless, and the attention to detail with lots of little extras was lovely. Beautiful and unique local artisan decor (will be getting an Andrew Pearce bowl!) The location is a few minutes walk to shops and restaurants, making everything convenient. Only complaint is we didn’t meet the doggies, will request a visit next time ;) We will definitely stay here again and highly recommend it.

Jimmy was an amazing host! we had an incredible stay and definitely will be back!

We had a lovely stay in Woodstock at Stay at Jimmy's in the Fall! The room was clean and comfortable (especially the soaking tub!) and our hosts were in contact with us throughout our stay. The drinks, snacks, and croissants were plentiful. Our room had a dedicated entrance so we could come and go easily, and we were right downtown, which was great for exploring and heading out for dinner and drinks. We appreciated that the property is adults only and were excited to learn that pets are welcome. We'll keep Stay at Jimmy's on our list for a future VT trip and plan to take our pup next time!

We stayed for one night and then we took the hot Pilates session in the morning. We loved it! The room is super cozy, modern and has lots of snacks. Jimmy was a great coach as well. Will be back!

just left jimmy’s today and couldn’t sing its praises enough. we were in the chill room which had a great sitting area, large bathroom and shower with a comfy king sized bed. treats were abundant and loved the holiday decor in the room. really made for an extra cozy feel. the location is walking distance from all shopping and right next to a market for any extras outside of what is provided you might need. while we didn’t need to bother jimmy for refills during our stay, we knew he was readily available to help in anyway. will definitely stay again if we’re back in the area and maybe even bring our pup!

Stay at Jimmy’s made our trip to Woodstock effortless and relaxing!!! From the moment we arrived, our hosts were genuinely welcoming and available, without ever being intrusive. The vibe throughout the property is warm, quiet, and cozy, which made it easy to truly relax after a day out. One of our favorite parts was the breakfast setup: there was a great variety of breakfast foods along with snacks, fruit, and plenty of water, plus coffee always available- all without leaving your room! It felt thoughtful and generous—like they had anticipated what travelers actually want. Our room was especially comfortable: warm, quiet, and beautifully decorated with a charming, intentional style, with a very special touch for the Christmas/New Year’s holidays. It also had all the amenities that make a stay feel convenient rather than “make-do”—a coffee maker, microwave, and refrigerator—so we could keep things simple and comfortable on our own schedule. Logistics were a breeze too. Parking was easy, and it’s pet friendly, which is a big plus. Location-wise, it’s hard to beat: close to everything, and less than a 5-minute walk to the center of Woodstock. We loved being able to park once and just wander. A standout bonus was the yoga studio and classes—such a nice touch, and a perfect way to start (or reset) your day. Overall, Stay at Jimmy's is cozy, well-equipped, thoughtfully hosted, and in a prime location. We’d absolutely stay here again! Martin and Arlean

An absolute pleasure to have stayed at Jimmy’s. The experience was incredible as we felt like we were the most important people on earth. We highly recommend Jimmy’s place.

Just finished our stay at Jimmy's. Wonderful hosts, impeccably decorated and a great location. Could not have asked for more. Will absolutely return in the future.