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Stay At Jimmy's

3.0 star property
Bed & breakfast in Woodstock with free breakfast

Photo gallery for Stay At Jimmy's

Front of property
Signature Double Room, Garden View
Signature Double Room, Courtyard View
Front of property
Signature Double Room, Courtyard View

Popular amenities

  • Pet-friendly
  • Air conditioning
  • Kitchen
  • Parking included
  • Free WiFi
The current price is AU$384
includes taxes & fees
28 July - 29 July

Explore the area

Map
45 Pleasant St, Woodstock, VT, 05091
  • Marsh-Billings-Rockefeller National Historical Park
    ‪13 min walk‬
  • Woodstock Town Hall Theatre
    ‪15 min walk‬
  • Billings Farm and Museum
    ‪16 min walk‬
  • Springfield, VT (VSF-Hartness State)
    ‪50 min drive‬

Room options

View all photos for Signature Suite, Garden View

Signature Suite, Garden View

Signature Suite, Garden View

10.0 out of 10
Exceptional
(2 reviews)

Highlights

Garden
Separate sitting area
Individually furnished
Individually decorated
Private indoor hot tub
Air conditioning
Heating
Kitchenette
  • 44 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for Signature Double Room, Courtyard View

Signature Double Room, Courtyard View

Signature Double Room, Courtyard View

10.0 out of 10
Exceptional
(5 reviews)

Highlights

Garden
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

Signature Double Room, Garden View

10.0 out of 10
Exceptional
(1 review)

Highlights

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

About the area

Woodstock

At Stay At Jimmy's you'll be within a short 5-minute stroll of Mt Ascutney Hospital and Health Center Primary Care - Woodstock and Ottauquechee Health Center. Highlights at this B&B include free continental breakfast, free self-parking and in-room kitchenettes. .This pet-friendly bed & breakfast offers free WiFi in public areas. Each morning free breakfast is served. Bring your pet along and take advantage of this property's pet-friendly amenities, such as food and water bowls. .Within a 30-minute drive of this 3-property class Woodstock B&B, attractions include Dartmouth College and Killington Resort.
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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

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

Restaurants

  • ‪Maplefield At Woodstocks - ‬5 min walk
  • ‪Woodstock Farmers Market - ‬4 min drive
  • ‪The Red Rooster - ‬11 min walk
  • ‪The Skinny Pancake - ‬10 min drive
  • ‪Worthy Kitchen - ‬13 min walk

About this property

Stay At Jimmy's

Bed & breakfast in Woodstock with free breakfast
Free breakfast is available daily. WiFi is free in public spaces. Free self parking is available.
  • 3 guestrooms or units
  • Continental breakfast (free)
Stay At Jimmy's offers 3 air-conditioned accommodations with complimentary slippers and a hairdryer. Each accommodation is individually furnished and decorated. Accommodation at this 3-star bed & breakfast has kitchenettes with microwaves and kitchenware and utensils. Bathrooms include baths or showers with in-room jetted baths and a rainfall showerhead, and bidets.

Guests can surf the web using complimentary wireless Internet access. 55-inch Smart televisions come with digital channels and Netflix. An iron/ironing board, change of towels and change of bedsheets can be requested. Housekeeping is provided on request.

Languages

Afrikaans, English, Spanish

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  • Parking included
  • Free WiFi
  • Air conditioning
4.4 out of 5, Excellent, 788 reviews
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Property amenities

Internet

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

Parking and transport

  • 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 lift
  • 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 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: USD 75 per accommodation, per stay (maximum USD 75 per stay)
  • Food and water bowls are available
    • Service animals are exempt from fees.

Children and extra beds

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

Payment types

Important information

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

  • Pet fee: USD 75 per accommodation, per stay (maximum USD75 per stay)
  • Service animals are exempt from fees

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

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 and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children. If you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room. This property accepts Visa, Mastercard and debit cards. Cash is not accepted. 

We should mention

  • Children 18 years old and younger aren't allowed 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

What is the cancellation policy at Stay At Jimmy's?

Stay At Jimmy's offers free cancellation on select room rates. Check out the cancellation policy for more info.

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

As of 27 July 2025, prices found for a 1-night stay for 2 adults at Stay At Jimmy's on 28 July 2025 start from AU$383.65, including 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.

Is parking available at Stay At Jimmy's?

Yep, Stay At Jimmy's has a free self car park.

Are there hot tubs in the rooms at Stay At Jimmy's?

No, but there are Jetted bath in the guestrooms.

Does Stay At Jimmy's serve breakfast?

Yeah, complimentary continental brekkie is offered daily between 7:00 AM and 9:00 AM.

Is there a free airport shuttle available at Stay At Jimmy's?

No, Stay At Jimmy's does not offer an airport shuttle service.

What time are check-in & check-out at Stay At Jimmy's?

Check-in begins at 3:00 PM. Check-out time is 11:00 AM.

Are pets allowed at Stay At Jimmy's?

Furry friends are welcome at Stay At Jimmy's, with food and water bowls on offer.

Stay At Jimmy's Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 37 out of 38 reviews
Rating 8 - Good. 1 out of 38 reviews
Rating 6 - Okay. 0 out of 38 reviews
Rating 4 - Poor. 0 out of 38 reviews
Rating 2 - Terrible. 0 out of 38 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

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

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

Ahren

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night 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

Travelled with partner
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

Jessica

Travelled with partner
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

Abigail

Travelled with partner
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

Patricia

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Sep 2024

10/10 Excellent

Dennis

Travelled with partner
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

Bonnie, Westford

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

10/10 Excellent

Cathy

Liked: Cleanliness, staff & service, property conditions & facilities
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.
Stayed 3 nights in Oct 2024

10/10 Excellent

kathryn

Travelled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
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.
Stayed 2 nights in Oct 2024

10/10 Excellent

Elise

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Jimmy’s combines quaint and modern flawlessly! The wrap around porch was perfect for our rainy evening (several fire pits available too).
Stayed 1 night in Sep 2024

10/10 Excellent

John

Travelled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
Charming and attentive hosts. Perfect spot to relax and enjoy Woodstock. I highly recommend Stay at Jimmys
Stayed 2 nights in Aug 2024

10/10 Excellent

MacKenzie

Travelled with family, Travelled with pets
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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!
Stayed 1 night in Aug 2024

10/10 Excellent

Laura

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

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!!!
Stayed 2 nights in Aug 2024

10/10 Excellent

Haeden

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Jimmy’s is the bees knees
Stayed 1 night in Jul 2024

10/10 Excellent

James

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Jimmy's is just the absolute best
Stayed 1 night in Jul 2024

10/10 Excellent

Randy

Business traveller
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Jul 2024

10/10 Excellent

Daniele

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 1 night in Jul 2024

10/10 Excellent

bridget

Travelled with partner
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

Steven

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

10/10 Excellent

Winnett

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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!
Stayed 1 night in Jun 2024