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Stay At Jimmy's

3.0 star property
B&B in Woodstock

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Photo gallery for Stay At Jimmy's

Front of property
Signature Double Room, Courtyard View | 1 bedroom, individually decorated, individually furnished
Signature Double Room, Garden View | 1 bedroom, individually decorated, individually furnished
Signature Double Room, Courtyard View | 1 bedroom, individually decorated, individually furnished
Front of property
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.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Pet friendly
  • Air conditioning
  • Free parking
  • Free WiFi

Main amenities (2)

  • Housekeeping (on request)
  • Air conditioning

Feel at home (6)

  • Kitchenette
  • Private bathroom
  • Yard
  • Bathtub or shower
  • Digital TV service
  • Jetted bathtub
The current price is NT$7,627
NT$8,390 total
includes taxes & fees
Sep 14 - Sep 15

Room options

Check availability for these dates

Tonight

Sep 3 - Sep 4
Check availability for tonight Sep 3 - Sep 4

Tomorrow

Sep 4 - Sep 5
Check availability for tomorrow Sep 4 - Sep 5

View all photos for Signature Suite, Garden View

Signature Suite, Garden View | 1 bedroom, individually decorated, individually furnished

Signature Suite, Garden View

10.0 out of 10
Exceptional
(2 reviews)

Highlights

Yard
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

View all photos for Signature Double Room, Courtyard View

Signature Double Room, Courtyard View | 1 bedroom, individually decorated, individually furnished

Signature Double Room, Courtyard View

10.0 out of 10
Exceptional
(5 reviews)

Highlights

Yard
Individually furnished
Individually decorated
Air conditioning
Heating
Kitchenette
Mini-fridge
Smart TV
  • 17 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for Signature Double Room, Garden View

Signature Double Room, Garden View | 1 bedroom, individually decorated, individually furnished

Signature Double Room, Garden View

9.0 out of 10
Wonderful
(2 reviews)

Highlights

Yard
Individually furnished
Individually decorated
Air conditioning
Heating
Kitchenette
Mini-fridge
Smart TV
  • 16 sq m
  • Sleeps 2
  • 1 King Bed

Similar properties

Property grounds

The Shire Woodstock

  • Pet friendly
  • Free parking
  • Free WiFi
  • Air conditioning
8.8 out of 10, Excellent, 815 reviews
The Shire Woodstock
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About the neighborhood

Map
45 Pleasant St, Woodstock, VT, 05091

What's nearby

  • Marsh-Billings-Rockefeller National Historical Park - 13 min walk - 1.1 km
  • Woodstock Town Hall Theatre - 15 min walk - 1.3 km
  • Billings Farm and Museum - 16 min walk - 1.4 km
  • Woodstock Country Club - 3 min drive - 1.8 km
  • VINS Nature Center - 4 min drive - 2.2 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
  • ‪The Skinny Pancake Quechee - ‬10 min drive
  • ‪The Public House - ‬13 min drive
  • ‪Simon Pearce Restaurant, Retail & Glassblowing - ‬11 min drive
  • ‪The Red Rooster - ‬11 min walk

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

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
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

Here's the breakdown, no surprises

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

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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Stay At Jimmy's Reviews

Reviews

10

Exceptional

10/10

Cleanliness

10/10

Staff & service

10/10

Amenities

10/10

Property conditions & facilities

9.8/10

Eco-friendliness

Reviews

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

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

10/10 Exceptional

The owners of Jimmy's went above and beyond in every way and the room was fantastic!
Jessica, 2-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, 1-night trip

10/10 Exceptional

New B&B in VT

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

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

10/10 Exceptional

Good ownership, very helpful
Frederick, 1-night trip

10/10 Exceptional

Charming and attentive hosts. Perfect spot to relax and enjoy Woodstock. I highly recommend Stay at Jimmys
John, 2-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, 1-night trip

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

10/10 Exceptional

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!
MacKenzie, 1-night trip

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

10/10 Exceptional

Jimmy's is just the absolute best
James, 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, 1-night trip

10/10 Exceptional

Jimmy’s is the bees knees
Haeden, 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, 1-night trip

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

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

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

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, 1-night trip

10/10 Exceptional

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 !).
John, 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, 1-night trip

10/10 Exceptional

Stephen, 2-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, 4-night trip

10/10 Exceptional

Ahren, 1-night trip