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Stay At Jimmy's

3.0 star property
B&B in Woodstock

Choose dates to view prices

When visiting Woodstock, Stay At Jimmy's is a great choice to consider. Free perks include WiFi, self parking, and continental breakfast daily between 7:00 AM and 9:00 AM.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Pet friendly
  • Free WiFi
  • Air conditioning

Main amenities (2)

  • Housekeeping (on request)
  • Air conditioning

Feel at home (6)

  • Kitchenette
  • Private bathroom
  • Yard
  • Bathtub or shower
  • Digital TV service
  • Jetted bathtub

Room options

View all photos for Signature Double Room, Courtyard View

Signature Double Room, Courtyard View | Individually decorated, individually furnished, laptop workspace

Signature Double Room, Courtyard View

10.0 out of 10
Exceptional
(5 reviews)
  • 17 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Signature Double Room, Garden View

Signature Double Room, Garden View | Individually decorated, individually furnished, laptop workspace

Signature Double Room, Garden View

9.0 out of 10
Wonderful
(2 reviews)
  • Garden view
  • 16 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Signature Suite, Garden View

Signature Suite, Garden View | Individually decorated, individually furnished, laptop workspace

Signature Suite, Garden View

10.0 out of 10
Exceptional
(3 reviews)
  • Garden view
  • 44 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

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About the neighborhood

Map
45 Pleasant St, Woodstock, VT, 05091

What's nearby

  • Billings Park and Trail - 8 min walk - 0.7 km
  • Red Wagon Toy Company - 8 min walk - 0.7 km
  • Marsh-Billings-Rockefeller National Historical Park - 11 min walk - 1.0 km
  • Woodstock Town Hall Theatre - 15 min walk - 1.3 km
  • Billings Farm and Museum - 16 min walk - 1.4 km

Getting around

  • Lebanon, NH (LEB-Lebanon Municipal) - 21 min drive
  • Springfield, VT (VSF-Hartness State) - 34 min drive
  • Rutland, VT (RUT-Rutland Southern Vermont Regional) - 53 min drive
  • White River Junction Station - 22 min drive
  • Windsor Station - 24 min drive

Restaurants

  • ‪Cumberland Farms - ‬6 min walk
  • ‪Dunkin' - ‬11 min drive
  • ‪Simon Pearce Restaurant, Retail & Glassblowing - ‬11 min drive
  • ‪The Red Rooster - ‬11 min walk
  • ‪Worthy Kitchen - ‬13 min walk

About this property

Stay At Jimmy's

  • When visiting Woodstock, Stay At Jimmy's is a great choice to consider. Free perks include WiFi, self parking, and continental breakfast daily between 7:00 AM and 9:00 AM.

At a glance

DONE

Hotel size

    • 3 rooms
DONE

Arriving/Leaving

    • Check-in start time: 3:00 PM; Check-in end time: 11:30 PM
    • Minimum check-in age: 21
    • Check-out time is 11:00 AM
DONE

Special check-in instructions

    • 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 check-in instructions and an access code; your host will greet you
    • Information provided by the property may be translated using automated translation tools
DONE

Required at check-in

    • Credit card, debit card, or cash deposit required for incidental charges
    • Government-issued photo ID may be required
    • Minimum check-in age is 21
DONE

Children

    • Children (18 years old and younger) not allowed
DONE

Pets

    • Pets allowed*
    • Service animals welcome
    • Food and water bowls available
WIFI

Internet

    • Free WiFi in public areas
    • Free WiFi in rooms
LOCAL_PARKING

Parking

    • Free uncovered onsite self parking
    • Wheelchair-accessible parking and van parking on site

Property amenities

Food and drink

  • Free continental breakfast each morning 7:00 AM–9:00 AM

Accessibility

  • Wheelchair-accessible parking
  • 4 on-site accessible parking spaces
  • Wheelchair-accessible van parking
  • Wheelchair-accessible fitness center
  • Front entrance ramp
  • Well-lit path to entrance
  • Stair-free path to entrance
  • Area rugs in room
  • Hardwood flooring in room

Room amenities

Be entertained

  • 55-inch Smart TV
  • Digital TV channels
  • Netflix
  • Hulu
  • Streaming services

Home comfort

  • Air conditioning and heating
  • Slippers
  • Iron/ironing board (on request)

What to enjoy

  • Yard
  • Individually furnished and decorated

Freshen up

  • Private bathroom
  • Jetted bathtub
  • Bathtub or shower
  • Rainfall showerhead
  • Bidet
  • Hair dryer
  • Towels

Stay connected

  • Laptop-friendly workspace
  • Free WiFi

Food and drink

  • Mini-fridge
  • Microwave
  • Kitchenette
  • Cookware, dishes, and utensils
  • Coffee grinder

More

  • Housekeeping on request
  • Restaurant dining guide

Fees & policies

Renovations and closures

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

Pets

  • Service animals exempt from fees
  • Pets are allowed for an extra charge of USD 75 per accommodation, per stay (maximum USD 75 per stay)

Policies

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.

This property does not have elevators.

This property accepts credit cards and debit cards. Cash is not accepted.

Credit cards accepted: Visa, Mastercard

Also known as

Stay At Jimmy's Woodstock

Stay At Jimmy's Bed & breakfast

Stay At Jimmy's Bed & breakfast Woodstock

Frequently asked questions

Is Stay At Jimmy's currently open?

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

Does Stay At Jimmy's offer free cancellation for a full refund?

Yes, Stay At Jimmy's does have fully refundable room rates available to book on our site. If you’ve booked a fully refundable room rate, this can be cancelled up to a few days before check-in depending on the property's cancellation policy. Just make sure to check this property's cancellation policy for the exact terms and conditions.

Are pets allowed at Stay At Jimmy's?

Yes, pets are welcome. There's a charge of USD 75 per accommodation, per stay. Service animals are exempt from fees. Food and water bowls are available.

Is parking offered on site at Stay At Jimmy's?

Yes, there's free self parking.

What are the check-in and check-out times at Stay At Jimmy's?

Check-in start time: 3:00 PM; Check-in end time: 11:30 PM. Check-out time is 11:00 AM.

Does Stay At Jimmy's have rooms with private hot tubs?

Yes, each room has a jetted bathtub.

Does Stay At Jimmy's have self-catered rooms fitted with kitchens or kitchenettes?

Yes, a kitchenette is available in every room, and also includes a microwave, cookware, and a coffee grinder.

Does Stay At Jimmy's have any outdoor private spaces?

Yes, every room features a yard.

What's the area around Stay At Jimmy's like?

Stay At Jimmy's is a short 13-minute walk from Marsh-Billings-Rockefeller National Historical Park and 13 minutes' walk from Woodstock Town Hall Theatre.

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Reviews

Reviews

10

Exceptional

10

Cleanliness

10

Amenities

10

Staff & service

10

Property conditions & facilities

Guest review summary

What guests liked

  • The property is super dog friendly and welcomes pets with open arms. (4 reviews)
  • Breakfast was provided in the room and included a variety of items such as muffins, coffee, and snacks. (4 reviews)
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From real guest reviews summarized by AI.

Reviews

Verified

10/10 Exceptional

Wonderful amenities, location, and team, Highly recommend and would love to stay again
Heather, 1-night trip
Verified

10/10 Exceptional

Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!
Thomas, 1-night trip
Verified

10/10 Exceptional

New B&B in VT

Great hosts and very comfortable room.
Zachary, 1-night trip
Verified

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, 3-night trip
Verified

10/10 Exceptional

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.
CLARA, 1-night trip
Verified

10/10 Exceptional

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!
Lois, 1-night trip
Verified

10/10 Exceptional

Charming and attentive hosts. Perfect spot to relax and enjoy Woodstock. I highly recommend Stay at Jimmys
John, 2-night trip
Verified

10/10 Exceptional

Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return.
Monique, 1-night trip
Verified

10/10 Exceptional

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.
Cathy, 3-night trip
Verified

10/10 Exceptional

The owners of Jimmy's went above and beyond in every way and the room was fantastic!
Jessica, 2-night trip
Verified

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, 3-night trip
Verified

10/10 Exceptional

Super modern, comfortable, and clean. Jimmy provided everything we could possibly need. Highly recommend!
Hilary, 1-night trip
Verified

10/10 Exceptional

Jimmy’s combines quaint and modern flawlessly! The wrap around porch was perfect for our rainy evening (several fire pits available too).
Elise, 1-night trip
Verified

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, 1-night trip
Verified

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, 1-night trip
Verified

10/10 Exceptional

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!
David, 1-night trip
Verified

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, 1-night trip
Verified

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, 1-night trip
Verified

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, 1-night trip
Verified

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, 1-night trip
Verified

10/10 Exceptional

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!
Winnett, 1-night trip
Verified

10/10 Exceptional

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.
Daniele, 1-night trip
Verified

10/10 Exceptional

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.
kathryn, 2-night trip
Verified

10/10 Exceptional

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!!!
Laura, 2-night trip
Verified

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, 2-night trip