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Exterior & Views 1, Stay At Jimmy's, Windsor
Bedroom 2, Stay At Jimmy's, Windsor
Bathroom 3, Stay At Jimmy's, Windsor
Others 4, Stay At Jimmy's, Windsor
Others 5, Stay At Jimmy's, Windsor
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Guest House

Stay At Jimmy's

Windsor, Vermont

The Fun Awaits

Perfect for nature lovers
Perfect for nature loversOnly 719 m to Billings Park and Trail and 2.3 km to Mount Tom Peak
Tourist attractions nearby
Tourist attractions nearbyOnly 4.7 km to Union Arena Community Center

Reviews

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5.0/5
FantasticFrom 43 reviews
5.0/516 Mar 2026
michael • Couple Trip
Very cool space- a lottle unorthodox, but so much the better!
5.0/53 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!
5.0/523 Jan 2026
Heather • Family Trip
Wonderful amenities, location, and team, Highly recommend and would love to stay again
5.0/520 Oct 2025
CLARA • Couple Trip
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.
5.0/57 Oct 2025
Erin • Couple Trip
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!
5.0/52 Oct 2025
Catherine • Couple Trip
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.
5.0/53 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!
5.0/528 Aug 2025
Julie • Family Trip
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.
5.0/59 Aug 2025
Gary
Short walk to downtown Woodstock. Breakfast was included and provided in our room.
5.0/516 Jul 2025
Scott
Superb stay in all ways!
5.0/514 Jul 2025
Benjamin • Couple Trip
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!
5.0/59 Jul 2025
Hilary • Couple Trip
Super modern, comfortable, and clean. Jimmy provided everything we could possibly need. Highly recommend!
5.0/51 Jul 2025
joanne • Trip with Friends
Jimmy and his family (pets and partner) are wonderful. The place is clean, welcoming and in a great location. Grateful for a memorable visit!
5.0/527 Jun 2025
Robert • Couple Trip
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
5.0/525 Jun 2025
Thomas • Family Trip
Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!
5.0/515 Jun 2025
Sandra • Couple Trip
Jimmy and John were amazing hosts! Very communicative!
5.0/513 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.
5.0/531 Mar 2025
Monique
Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return.
5.0/521 Feb 2025
kirk
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!
5.0/515 Feb 2025
Frederick • Couple Trip
Good ownership, very helpful

Location

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45 Pleasant St, Woodstock, Vermont, US
All distances are measured in straight lines. The actual travel distance may be different.

Accommodation Rules

Announcement

Pets are accepted upon request and will have a $75.00 USD charge per stayGuests are required to show a photo identification and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply.Managed by a private host
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Check-in Procedure
Check-in3:00 PM-11:30 PM
Check-out11:00

  • Extra-person charges may apply and vary depending on property policy
  • Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
  • Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
  • This property accepts credit cards and debit cards; cash is not accepted
  • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

There is no front desk at this property. Guests planning to arrive outside of normal check-in hours will receive an email within 24 hours before arrival with special check-in instructions and an access code. The host will greet guests on arrival.Information provided by the property may be translated using automated translation tools.

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Want to check in early? Fill out the Special Requests form on the booking page.

More Policies
  • Children 18 years old and younger are not permitted at this property.

About Stay At Jimmy's

Stay At Jimmy's Location
With a stay at Stay At Jimmy's in Woodstock, you'll be within a 15-minute drive of Quechee Gorge Bridge and Green Mountain National Forest. This bed & breakfast is 18.1 mi (29.1 km) from Dartmouth College and 15.4 mi (24.8 km) from Killington Resort.

Stay At Jimmy's Rooms
Make yourself at home in one of the 3 individually decorated guestrooms, featuring kitchenettes. 55-inch Smart televisions with digital programming provide entertainment, while complimentary wireless internet access keeps you connected. Private bathrooms have jetted bathtubs and rainfall showerheads. Conveniences include microwaves, housekeeping is provided on request, and irons/ironing boards can be requested.

Restaurant and Cafe
A complimentary continental breakfast is served daily from 7:00 AM to 9:00 AM.

Important Information
This property is closed from November 1 2026 to March 22 2028 (dates subject to change).

Room Type and Price

Wed, 05 Aug 2026 - Thu, 06 Aug 2026 (1 night)
1 Room, 1 Adult, 0 Children