Stay At Jimmy's

10/10

Exceptional

15 Mar 2026

michael

Very cool space- a lottle unorthodox, but so much the better!

Partner

10/10

Exceptional

03 Mar 2026

Meghan

We've stayed at Jimmy's a couple of times and have had great experiences both visits. Highly recommend if you're in the Woodstock area!

10/10

Exceptional

23 Jan 2026

Heather

Wonderful amenities, location, and team, Highly recommend and would love to stay again

Leisure Family

10/10

Exceptional

20 Oct 2025

CLARA

This property is conveniently located with on site parking. It is about 10 mins walk into downtown, there are restaurants, coffee shops and ice cream shops. Room was great, everything you needed was thought of. I would recommend it very much.

Leisure Partner

10/10

Exceptional

06 Oct 2025

Erin

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!

Partner

10/10

Exceptional

02 Oct 2025

Catherine

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.

Partner

10/10

Exceptional

03 Sep 2025

David

What a wonderful and unique property! We were met by John (partner of Jimmy) and he very affable and willing to help. Wonderful breakfast bakeries were already awaiting. The room was awesome-highly functional and also quirky in a good way. The wrap around porch is gorgeous with nice areas to sit and chat. We would definitely book with Stay at Jimmy’s again!

10/10

Exceptional

28 Aug 2025

Julie

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.

Friends_and_family Family

10/10

Exceptional

09 Aug 2025

Gary

Short walk to downtown Woodstock. Breakfast was included and provided in our room.

8/10

Excellent

21 Jul 2025

Kathryn Ann

Everything was amazing!!! We will definately go back.

Leisure Partner

10/10

Exceptional

16 Jul 2025

Scott

Superb stay in all ways!

10/10

Exceptional

14 Jul 2025

Benjamin

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!

Leisure Partner

10/10

Exceptional

09 Jul 2025

Hilary

Super modern, comfortable, and clean. Jimmy provided everything we could possibly need. Highly recommend!

Leisure Partner

10/10

Exceptional

30 Jun 2025

joanne

Jimmy and his family (pets and partner) are wonderful. The place is clean, welcoming and in a great location. Grateful for a memorable visit!

Leisure Friends

10/10

Exceptional

27 Jun 2025

Robert

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

Leisure Partner

10/10

Exceptional

25 Jun 2025

Thomas

Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!

Leisure Family

10/10

Exceptional

15 Jun 2025

Sandra

Jimmy and John were amazing hosts! Very communicative!

Leisure Partner

10/10

Exceptional

12 May 2025

Gary

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.

10/10

Exceptional

30 Mar 2025

Monique

Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return.

10/10

Exceptional

21 Feb 2025

kirk

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!

10/10

Exceptional

15 Feb 2025

Frederick

Good ownership, very helpful

Partner

10/10

Exceptional

20 Jan 2025

Susan

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.

Leisure Partner

10/10

Exceptional

14 Jan 2025

Jessica

The owners of Jimmy's went above and beyond in every way and the room was fantastic!

Leisure Partner

10/10

Exceptional

08 Dec 2024

Abigail

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!!

Leisure Partner

10/10

Exceptional

18 Nov 2024

Dennis

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.

Leisure Partner

10/10

Exceptional

15 Nov 2024

Lois Renee

Wonderful rooms!

Beautiful little inn with wonderful owners! Will definitely stay there again!

Partner

10/10

Exceptional

29 Oct 2024

Bonnie

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!

10/10

Exceptional

13 Oct 2024

Cathy

The location was great. Although not a bed and breakfast, the host offers lots of home-baked goodies (muffins,cookies breads, etc. we enjoyed our stay and felt we were very well taken care of.

Leisure

10/10

Exceptional

03 Oct 2024

kathryn

We had an amazing time at Stay at Jimmys. Convenient parking and easy walk into town. When we arrived , our room was ready and the hosts, Jimmy and John were awesome. we had our own little porch area with muffins, coffee, fruit and drinks ready in our room! Private and very quiet and the hosts were easily accessible! . Definitely going back. Perfect place to stay in Woodstock.

Leisure Partner

10/10

Exceptional

09 Sep 2024

Elise

Jimmy’s combines quaint and modern flawlessly! The wrap around porch was perfect for our rainy evening (several fire pits available too).

Partner

10/10

Exceptional

02 Sep 2024

John

Charming and attentive hosts. Perfect spot to relax and enjoy Woodstock. I highly recommend Stay at Jimmys

Leisure Partner

10/10

Exceptional

18 Aug 2024

MacKenzie

Jimmy and John were so welcoming and made our stay in Woodstock exceptional! Not only were they kind to us, but also to our dog who loved her time at the property as well. We can't wait to go back!

Leisure Pet

10/10

Exceptional

18 Aug 2024

Laura

STAY HERE!!!!

Our stay was AMAZING! Jimmy and John are the perfect hosts. The fresh fruit and baked items, the beautiful grounds, the private fire pit, the comfortable apartment, the perfect location, and the way our hosts made us feel so comfortable, well, we just truly hated to leave.

Thank you Jimmy and John for an amazing, (too brief), stay at your BnB!!!

Partner

10/10

Exceptional

26 Jul 2024

Haeden

Jimmy’s is the bees knees

Leisure Family

10/10

Exceptional

24 Jul 2024

James

Jimmy's is just the absolute best

10/10

Exceptional

22 Jul 2024

Daniele

My wife and I recently stayed at \"Stay at Jimmy's\", and it was a delightful experience. The rooms were impeccably clean and tastefully decorated, providing a cozy and inviting atmosphere. Jimmy & John's hospitality was top-notch, with a friendly and accommodating demeanor that made us feel right at home. \"Stay at Jimmy's\" exceeded our expectations, and I would highly recommend it to anyone seeking a charming and comfortable stay.

Leisure Family

10/10

Exceptional

21 Jul 2024

bridget

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!

Leisure Partner

10/10

Exceptional

06 Jul 2024

Paul

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!

10/10

Exceptional

22 Jun 2024

Winnett

We had a great time at Stay at Jimmy’s! The rooms are well appointed and very comfortable. Our bathroom had a huge tub and beautiful shower. We loved walking into town to get coffee! The rooms were very clean and modern. We will be back thank you!

Leisure Family

10/10

Exceptional

07 Jun 2024

John

Our stay at Jimmy’s met all our expectations that we had hoped for in Woodstock. The accommodation is conveniently situated close to the heart of town and once we had parked our car it was easy to walk to the restaurants and shops. The room was impeccably appointed and spotlessly clean. Our hosts were extremely hospitable and personally welcomed us upon our arrival. Our stay was short and sweet but we will return when next in Woodstock. We would highly recommend a stay at Jimmy’s. Wonderful ( and it is pet friendly !).

10/10

Exceptional

02 Jun 2024

Zachary

New B&B in VT

Great hosts and very comfortable room.

Partner

10/10

Exceptional

05 May 2024

Lois

Short but sweet stay

Our short but sweet stay was great. Check in was smooth and the breakfast bundles were a nice touch. The rooms are newly designed and felt like such a getaway!

Partner

10/10

Exceptional

02 Nov 2024

Eloise

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 !

Partner