10/10 Exceptional
Superb stay in all ways!
Scott
Scott, 1-night trip
Stay At Jimmy's
B&B in Woodstock
Enjoy your visit to Woodstock with a stay at Stay At Jimmy's. Free perks include WiFi, self-parking and continental breakfast daily between 7:00 AM and 9:00 AM.
Exceptional
Popular amenities
- Pet-friendly
- Air conditioning
- Free WiFi
Main amenities (2)
- Housekeeping (on request)
- Air conditioning
Feel at home (6)
- Kitchenette
- Private bathroom
- Garden
- Bath or shower
- Digital TV service
- Jetted bath
£166
includes taxes & fees
17 Nov - 18 Nov
Room options
Check availability for these dates
Signature Double Room, Courtyard View
Exceptional
Highlights
Garden
Individually furnished
Individually decorated
Air conditioning
Heating
Kitchenette
Mini-fridge
Smart TV
- 17 sq m
- Sleeps 2
- 1 King Bed
Signature Double Room, Garden View
Wonderful
Highlights
Garden
Individually furnished
Individually decorated
Air conditioning
Heating
Kitchenette
Mini-fridge
Smart TV
- 16 sq m
- Sleeps 2
- 1 King Bed
Signature Suite, Garden View
Exceptional
Highlights
Garden
Separate sitting area
Individually furnished
Individually decorated
Private indoor hot tub
Air conditioning
Heating
Kitchenette
- 44 sq m
- 1 bedroom
- Sleeps 2
- 1 King Bed
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About the area
45 Pleasant St, Woodstock, VT, 05091
About this property
Stay At Jimmy's
Enjoy your visit to Woodstock with a stay at Stay At Jimmy's. Free perks include WiFi, self-parking and continental breakfast daily between 7:00 AM and 9:00 AM.
At a glance
Property amenities
Room amenities
Frequently asked questions
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Stay At Jimmy's Reviews
10
Exceptional
10/10
Cleanliness
10/10
Staff & service
10/10
Amenities
10/10
Property conditions & facilities
9.8/10
Eco-friendliness
8/10 Very good
Everything was amazing!!! We will definately go back.
Kathryn Ann
Kathryn Ann, 3-night trip
10/10 Exceptional
Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return.
Monique
Monique, 1-night trip
10/10 Exceptional
The owners of Jimmy's went above and beyond in every way and the room was fantastic!
Jessica
Jessica, 2-night trip
10/10 Exceptional
We were welcomed by John when we checked in. It was our 25th anniversary and in our room was the sweetest card and balloons to honor the occasion. So extremely thoughtful! The room was adorable and very comfortable. It had been outfitted with all the amenities you can think of…pastries and snacks, board games, toiletries, and a full kitchen. The only thing I regret is not staying longer in this charming B and B! We will absolutely be back when we visit Woodstock!
Erin
Erin, 1-night trip
10/10 Exceptional
Don’t hesitate to book this awesome place!!!! Very unique, modern and clean. So close to everything and many amenities, which were a welcome surprise!
bridget
bridget, 1-night trip
10/10 Exceptional
We had a great time! This is a new B&B and they aim to please. Jimmy made sure we were comfortable and felt welcome …. There were plenty of snacks and fruit and beverages available. The rooms were cozy and well-decorated. Bravo! We will come again!
Paul
Paul, 2-night trip
10/10 Exceptional
A really delightful stay hosted by stellar hosts! Great location only a few minutes walk to the centre of town. Property was spotless and everything within screams quality from the bedding to the bathroom tv art…….
My husband over indulged on the banana walnut bread as it was so scrumptious, lots of goodies for those with a sweet tooth, all top notch.
Would 100% stay here again.
The only thing to note is that in October (I’m not sure about other months)you’d better prebook restaurants a week or so ahead as it’s busy.
Catherine
Catherine, 2-night trip
10/10 Exceptional
Great Stay at Jimmy's!
Jimmy's was fantastic! I really want to have Jimmy design my house. Every detail was taken care of, comfortable bed, and decor was so fun! Loved the rainfall shower head. We met John, who was so warm and welcoming. Also met Mable and Matilda who were sweeties. We only stayed one night and wished that we had been able to stay longer. The location is very convenient.
Julie
Julie, 1-night trip
10/10 Exceptional
Short walk to downtown Woodstock. Breakfast was included and provided in our room.
Gary
Gary, 1-night trip
10/10 Exceptional
Stylish, clean, comfortable, and in the perfect location to start and end the day. The owners were lovely and accommodating, and the room was a treat for the eyes and a balm for the body. Couldn’t recommend more!
Benjamin
Benjamin, 3-night trip
10/10 Exceptional
Super modern, comfortable, and clean. Jimmy provided everything we could possibly need. Highly recommend!
Hilary
Hilary, 1-night trip
10/10 Exceptional
Jimmy and his family (pets and partner) are wonderful. The place is clean, welcoming and in a great location. Grateful for a memorable visit!
joanne
joanne, 3-night trip
10/10 Exceptional
Every little detail is taken care of... Every thought for the customers convenience.
Q-tips! What hotel supplies Q-tips? We were lucky enough to meet Jimmy... Nice guy, very welcoming.
Snacks, beverages... Fresh muffins and coffee.
I can't say enough about how wonderful our stay was... Price was very low for what you get.
Highly recommend
Robert
Robert, 1-night trip
10/10 Exceptional
Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!
Thomas
Thomas, 1-night trip
10/10 Exceptional
Jimmy and John were amazing hosts! Very communicative!
Sandra
Sandra, 1-night trip
10/10 Exceptional
4/28/25 Stay:
Exceeded expectations everywhere. Owners were very accessible and greeted us to make sure we had everything to make our experience memorable. Location was fabulous as very safe and walkable to anywhere in town. Convenient parking on premise. Room access was secure, comfortable, extremely clean, and appointed with every amenity you could think of and more. I will stay at Jimmy’s anytime I visit Woodstock and highly recommend you do so as well.
Gary
Gary, 1-night trip
10/10 Exceptional
An Incredible Getaway at Stay at Jimmy’s
We spent a wonderful week at Stay at Jimmy’s, with our dog Sofia (they are super dog friendly) and it was the perfect escape. From the moment we arrived, the hospitality was top-notch. The Relax Room was absolutely amazing—the whirlpool tub was the best we’ve ever used, making it the ideal place to unwind.
Every morning, we were treated to fresh-baked goods, a great selection of teas, coffee, and soft drinks, which made us feel right at home. The attention to detail in the interior design was impressive—every space was beautifully curated, warm, and inviting.
One of the most thoughtful touches was Jimmy surprising my wife with a birthday card during our stay, making the experience even more special. She also took a fantastic on-site yoga class, which she absolutely loved.
If you’re looking for a peaceful, rejuvenating getaway with incredible hospitality, Stay at Jimmy’s in Woodstock, VT is the perfect choice.
We can’t wait to come back!
kirk
kirk, 4-night trip
10/10 Exceptional
Good ownership, very helpful
Frederick
Frederick, 1-night trip
10/10 Exceptional
Stay at Jimmys is exceptional!
From the second you pull into the lot you are greeted with pure joy. Jimmy came out and introduced himself welcoming us to his beautiful Inn. I travel around the globe and have never been welcomed this beautifully in all my life.
The property is clean, peaceful, fabulously decorated. It’s so comfortable and welcoming.
We didn’t want to leave! And guess what? Jimmy told us we could stay as long as we wanted the day of check out beaches they didn’t have anyone coming in after us. Who does that?!? If we weren’t worried about the snow storm we would definitely have stayed a few more hours.
This is our new go to when visit family in VT.
Jimmy and John we’ll see you again.
Susan
Susan, 1-night trip
10/10 Exceptional
Our stay here was absolutely amazing! As soon as we walked in, we knew that we picked the right place. It was safe, clean and so close to downtown. John and Jimmy were the sweetest and made us feel right at home. We can’t recommend this place enough and will definitely be back!!
Abigail
Abigail, 1-night trip
10/10 Exceptional
Wow! Loved our visit at Stay at Jimmy's. Room was beautifully decorated and supplied with everything we needed. Location was perfect for exploring Woodstock. We had excellent communication from John and Jimmy. A bonus for us was the EV charging station across the street.
Dennis
Dennis, 1-night trip
10/10 Exceptional
Wonderful rooms!
Beautiful little inn with wonderful owners! Will definitely stay there again!
Lois Renee
Lois Renee, 1-night trip
10/10 Exceptional
Merveilleux
Il s’agit littéralement du meilleur hôtel que nous avons fait durant notre séjour ! Tout est extrêmement propre et bien pensé et les petites attentions étaient nombreuses… c’est un endroit dans lequel on se sent safe et très bien accueillis ! Merci infiniment à John et Jimmy pour cette pépite ! Si vous devez séjourner à Woodstock n’hésitez pas, c’est ici !
Eloise
Eloise, 1-night trip
10/10 Exceptional
I loved the attention to detail. We stay in a decent number of inns, B&Bs and hotels - most of which are excellent. This is the only one with decent tea AND agave. Some other distinguishing features: bidet, lots of snacks & refreshments, baked goods for breakfast already in room, adjustable-light mirror and embossed toilet paper. I loved that the rooms were not colonial decor with flowered bedding and traditional furniture - so common in this area. Very clean with the guest in mind!
Bonnie
Bonnie, 1-night trip
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