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Stay At Jimmy's

3.0 star property
Bed & breakfast in Woodstock with free breakfast

Choose dates to view prices

Photo gallery for Stay At Jimmy's

Front of property
Front of property
Signature Double Room, Courtyard View | 1 bedroom, individually decorated, individually furnished
Signature Double Room, Courtyard View | 1 bedroom, individually decorated, individually furnished
Signature Double Room, Garden View | 1 bedroom, individually decorated, individually furnished
Stay At Jimmy's provides free continental breakfast and more. Guests can connect to free in-room WiFi.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Pet friendly
  • Air conditioning
  • Kitchen
  • Free WiFi
The current price is ￥30,670
￥33,736 total
includes taxes & fees
Nov 3 - Nov 4

Room options

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

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
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About the neighborhood

Map
05091, VT, Woodstock, 45 Pleasant St

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 - 2 min drive - 1.8 km
  • VINS Nature Center - 3 min drive - 2.2 km

Getting around

  • White River Junction Station - 22 min drive
  • Lebanon, NH (LEB-Lebanon Municipal) - 21 min drive

Restaurants

  • ‪The Public House - ‬13 min drive
  • ‪The Skinny Pancake Quechee - ‬10 min drive
  • ‪Cumberland Farms - ‬6 min walk
  • ‪Simon Pearce Restaurant, Retail & Glassblowing - ‬11 min drive
  • ‪Dunkin' - ‬11 min drive

About this property

Stay At Jimmy's

Property highlights
Stay At Jimmy's provides free continental breakfast and more. Guests can connect to free in-room WiFi.
You'll also enjoy perks such as:
  • Free self parking
Room features
All guestrooms are individually furnished, and include comforts such as laptop-friendly workspaces and air conditioning, in addition to perks like free WiFi.
More amenities include:
  • Bathrooms with rainfall showers or jetted bathtubs plus bidets and hair dryers
  • 55-inch Smart TVs with Netflix, Hulu, and streaming services
  • Private yards, wardrobes/closets, and kitchenettes

Similar properties

Property grounds

The Shire Woodstock

  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
8.8 out of 10, Excellent, 870 reviews
The Shire Woodstock

Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transportation

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

Food and drink

  • Free continental breakfast available daily 7:00 AM to 9:00 AM

Guest services

  • Change of bedsheets (on request)
  • Change of towels on request
  • Housekeeping (on request)

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 4 accessible parking spaces
  • Area rugs in room
  • Front entrance ramp
  • Hardwood flooring in room
  • No elevator
  • Well-lit path to entrance
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible gym
  • Wheelchair-accessible parking
  • Wheelchair-accessible van parking

Room amenities

Bathroom

  • Bathtub or shower
  • Bidet
  • Hair dryer
  • Jetted bathtub or rainfall showerhead
  • Private bathroom
  • Slippers
  • Towels provided

Entertainment

  • 55-inch smart TV with digital channels
  • Hulu
  • Netflix
  • Streaming services

Food and drink

  • Coffee grinder
  • Cookware, dishware, and utensils
  • Kitchenette
  • Microwave
  • Mini-fridge
  • Restaurant dining guides

More

  • Air conditioning
  • Heating
  • Individual decor
  • Individual furnishings
  • Iron/ironing board on request
  • Laptop workspace

Policies

Check-in

Check-in start time: 3:00 PM; Check-in end time: 11:30 PM
Minimum check-in age: 21

Check-out

Check-out before 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

Access methods

Access code, host will greet you

Pets

Pets allowed for an extra charge of USD 75 per accommodation, per stay (maximum USD 75 per stay)
Service animals are welcome, and are exempt from fees
Food and water bowls are available

Children and extra beds

Children 18 and younger are not allowed at this property; All guests older than 18 are welcome

Property payment types

Important information

Optional extras

  • Pet fee: USD 75 per accommodation, per stay (maximum USD 75 per stay)
  • Service animals are exempt from fees

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

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

We should mention

This property does not have elevators
Children 18 years old and younger are not permitted at this property

Property is 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 pet-friendly?

Yes, pets are allowed at this property. There's a fee of USD 75 per accommodation, per stay. Service animals are exempt from fees.

How much does it cost to stay at Stay At Jimmy's?

As of Oct 31, 2025, prices found for a 1-night stay for 2 adults at Stay At Jimmy's on Nov 3, 2025 start from ￥30,670, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Stay At Jimmy's?

Self parking is free at this property.

What time is check-in at Stay At Jimmy's?

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

What time is check-out at Stay At Jimmy's?

Check-out is at 11:00 AM.

Where is Stay At Jimmy's located?

Situated in Woodstock, this bed & breakfast is within a 5-minute walk of Mt Ascutney Hospital and Health Center Primary Care - Woodstock and Ottauquechee Health Center. Red Wagon Toy Company and Billings Park and Trail are also within 10 minutes.

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Stay At Jimmy's Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 45 out of 46 reviews
Rating 8 - Good. 1 out of 46 reviews
Rating 6 - Okay. 0 out of 46 reviews
Rating 4 - Poor. 0 out of 46 reviews
Rating 2 - Terrible. 0 out of 46 reviews

10/10

Cleanliness

10/10

Staff & service

10/10

Amenities

10/10

Property conditions & facilities

9.8/10

Eco-friendliness

Reviews

10/10 Excellent

Thomas

Liked: Cleanliness, amenities, property conditions & facilities
Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!
Stayed 1 night in Jun 2025

10/10 Excellent

Scott

Liked: Cleanliness, staff & service, property conditions & facilities
Superb stay in all ways!
Stayed 1 night in Jul 2025

8/10 Good

Kathryn Ann

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything was amazing!!! We will definately go back.
Stayed 3 nights in Jul 2025

10/10 Excellent

Monique

Liked: Cleanliness, staff & service, property conditions & facilities
Jimmy greeted us as we arrived. Clean, modern suite with private entrance. We loved the place and plan to return.
Stayed 1 night in Mar 2025

10/10 Excellent

Jessica

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The owners of Jimmy's went above and beyond in every way and the room was fantastic!
Stayed 2 nights in Dec 2024

10/10 Excellent

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!
Stayed 1 night in Jul 2024

10/10 Excellent

Paul

Liked: Cleanliness, staff & service, property conditions & facilities
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!
Stayed 2 nights in Jul 2024

10/10 Excellent

John

Liked: Cleanliness, staff & service, property conditions & facilities
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 !).
Stayed 1 night in Jun 2024

10/10 Excellent

CLARA

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 1 night in Oct 2025

10/10 Excellent

David

Liked: Cleanliness, staff & service, property conditions & facilities
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!
Stayed 1 night in Aug 2025

10/10 Excellent

Gary

Liked: Cleanliness, staff & service, property conditions & facilities
Short walk to downtown Woodstock. Breakfast was included and provided in our room.
Stayed 1 night in Aug 2025

10/10 Excellent

Benjamin

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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!
Stayed 3 nights in Jul 2025

10/10 Excellent

Hilary

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Super modern, comfortable, and clean. Jimmy provided everything we could possibly need. Highly recommend!
Stayed 1 night in Jul 2025

10/10 Excellent

joanne

Liked: Cleanliness, amenities, property conditions & facilities
Jimmy and his family (pets and partner) are wonderful. The place is clean, welcoming and in a great location. Grateful for a memorable visit!
Stayed 3 nights in Jun 2025

10/10 Excellent

Robert

Liked: Staff & service, amenities, property conditions & facilities
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
Stayed 1 night in Jun 2025

10/10 Excellent

Sandra

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Jimmy and John were amazing hosts! Very communicative!
Stayed 1 night in Jun 2025

10/10 Excellent

Gary

Liked: Cleanliness, staff & service, property conditions & facilities
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.
Stayed 1 night in Apr 2025

10/10 Excellent

kirk

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

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!
Stayed 4 nights in Feb 2025

10/10 Excellent

Frederick

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Good ownership, very helpful
Stayed 1 night in Feb 2025

10/10 Excellent

Susan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 1 night in Jan 2025

10/10 Excellent

Abigail

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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!!
Stayed 1 night in Dec 2024

10/10 Excellent

Dennis

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 1 night in Nov 2024

10/10 Excellent

Lois Renee

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Wonderful rooms!

Beautiful little inn with wonderful owners! Will definitely stay there again!
Stayed 1 night in Nov 2024

10/10 Excellent

Eloise

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

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 !
Stayed 1 night in Nov 2024

10/10 Excellent

Bonnie

Liked: Cleanliness, staff & service, property conditions & facilities
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!
Stayed 1 night in Oct 2024