Stay At Jimmy's

B&B in Woodstock

Choose dates to view prices

Where to?

Dates

November 2025

16

December 2025

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

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

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
Yard
Bathtub or shower
Digital TV service
Jetted bathtub

CNY1,554 total

includes taxes & fees

Nov 17 - Nov 18

Room options

Check availability for these dates

Tonight

Nov 16 - Nov 17

Tomorrow

Nov 17 - Nov 18

Signature Double Room, Courtyard View

Exceptional

Highlights

Yard

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

Yard

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

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

Similar properties

Pet friendly
Free parking
Free WiFi
Air conditioning

Sign in to view eligible discounts and perks. More rewards for more adventures!

Sign in Sign up, it's free

About the neighborhood

45 Pleasant St, Woodstock, VT, 05091

What's nearby

Mt Ascutney Hospital and Health Center Primary Care - Woodstock - 3 min walk - 0.3 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
Woodstock Country Club - 2 min drive - 1.8 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

‪The Public House - ‬13 min drive
‪The Skinny Pancake Quechee - ‬10 min drive
‪Dunkin' - ‬11 min drive
‪Simon Pearce Restaurant, Retail & Glassblowing - ‬11 min drive
‪Mon Vert Cafe - ‬6 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

Hotel size

- 3 rooms

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

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

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

Children

- Children (18 years old and younger) not allowed

Pets

- Pets allowed*
- Service animals welcome
- Food and water bowls available

Internet

- Free WiFi in public areas
- Free WiFi in rooms

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

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.

Have a question?

Beta

Get instant answers with AI powered search of property information and reviews.

Ask a question

Stay At Jimmy's Reviews

10

Exceptional

10

Cleanliness

10

Amenities

10

Staff & service

9.8

Eco-friendliness

10

Property conditions & facilities

What guests liked

Convenient on-site parking was available and easily accessible. (3 reviews)
Freshly baked goodies, including muffins, cookies, and bread, were provided for breakfast. (4 reviews)

From real guest reviews summarized by AI.

10/10 Exceptional

Jul 16, 2025

Superb stay in all ways!

Scott, 1-night trip

8/10 Very good

Jul 21, 2025

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

Kathryn Ann, 3-night trip

10/10 Exceptional

Mar 31, 2025

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

Jan 15, 2025

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

Jessica, 2-night trip

10/10 Exceptional

Oct 7, 2025

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

10/10 Exceptional

Jul 21, 2024

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

Jul 7, 2024

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

Oct 2, 2025

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, 2-night trip

10/10 Exceptional

Aug 28, 2025

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

Aug 9, 2025

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

Gary, 1-night trip

10/10 Exceptional

Jul 14, 2025

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

10/10 Exceptional

Jul 9, 2025

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

Hilary, 1-night trip

10/10 Exceptional

Jul 1, 2025

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

10/10 Exceptional

Jun 27, 2025

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, 1-night trip

10/10 Exceptional

Jun 25, 2025

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

Thomas, 1-night trip

10/10 Exceptional

Jun 15, 2025

Jimmy and John were amazing hosts! Very communicative!

Sandra, 1-night trip

10/10 Exceptional

May 13, 2025

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

Feb 21, 2025

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

Feb 15, 2025

Good ownership, very helpful

Frederick, 1-night trip

10/10 Exceptional

Jan 20, 2025

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

Dec 9, 2024

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

Nov 18, 2024

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

Nov 15, 2024

Wonderful rooms!

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

Lois Renee, 1-night trip

10/10 Exceptional

Nov 2, 2024

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, 1-night trip

10/10 Exceptional

Oct 29, 2024

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