Planning perspective
What to consider before reaching out
A strong first conversation is about fit, not just availability. Share your date, approximate guest count, location, and the feeling you want the day to have. Ask what is included, what typically changes the final quote, and what decisions need to be made earliest.
For a hotel rooms partner, confirm how communication works, who will be present on the day, and how the team handles changes. Pricing was not included in the supplied research, so request a current, itemized proposal directly from the business.
In their clients’ words
What people say on Google
David Nolte
3 weeks ago
Great communication and updates when needed. Excellent instructions. The room (Hangout) was perfect, very clean, cool and well-stocked with goodies for us. Close to downtown, just a 10-minute walk so it was very easy to leave the car in the provided free parking behind the lodging. The room AC/heating unit was quiet and easy to operate. Did not bother much with the nice TV in the room. Only one minor nit - no facecloths provided but we enjoyed the rain shower and provided toiletries. This will be our first choice to stay when we visit Woodstock.
Kimberly Bishop
7 months ago
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!
Amanda T
a month ago
I cannot say enough good things about Stay at Jimmy's. My husband and I stayed here for one night last week. We loved that they were away from downtown and unlike some other places in Woodstock, we didn't need to book a two or three night minimum stay. John was extremely helpful with check in information and we were able to check in ourselves. The rooms as absolutely immaculate!! You walk into a small living area with a sink, cabinets and small fridge. There are also two TVs. Plenty of space for all your things! We had our breakfast waiting for us for the next morning of muffins and croissants. The bathroom is gorgeous and who doesn't love a rain shower? If you are looking for a place to sta...
Deanna Lentz
2 months ago
We only stayed one night at Jimmy’s, but wish we could have stayed another night. The location is great for exploring the Woodstock area. The room was comfortable and included a small kitchenette and sitting area separate from the bed. The hosts put a lot of effort into to making the room comfortable and welcoming. The provided snacks and breakfast pastries were great. I would definitely stay here again.
Kelly Yan
2 months ago
We had an incredibly stay! We fell in love with Woodstock during our trip here, and staying at Stay at Jimmy’s was a huge part of it. Beautiful and clean room, with delicious muffins, breads, candy bars, and beverages waiting for you. There was also a well-stocked snack bar in the hallway filled with additional items in case you ran out, all complimentary. After a conversation with Jimmy and telling him it was my fiancé’s birthday, he offered to make us lunch, which was DELICIOUS! Jimmy was so sweet and kind. And we met his friendly and cute cat, Mabel, which was also a big highlight of the trip!! We look forward to coming back!
Reviews from Google. Read all of them on Google.
Getting here
How far is this from home?
Pick the city you and most of your guests will be driving from and we will estimate the trip.
An estimate for planning, not live traffic. Leafy weekends in October always take longer.
For your guests
Lovely places to stay nearby
Woodstock Inn & Resort
The anchor hotel in the village, ideal for a room block.
Kedron Valley Inn, South Woodstock
Country rooms minutes from the village green.
Twin Farms, Barnard
An all-inclusive splurge for the wedding night.
Three stops worth the detour
Somewhere pretty for photographs, and somewhere warm for a good cup of coffee.
Sleepy Hollow Farm, Pomfret
The most photographed farm lane in Vermont.
Quechee Gorge
A bridge walk over Vermont's deepest gorge.
Mon Vert Cafe, Woodstock
Warm little cafe on the corner for coffee and pastries.
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Editorial note: this profile is based only on the vendor research supplied to New England Celebrations. It is not a paid endorsement, interview, or first-person testimonial. Pricing and availability are on request.