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Stay At Jimmy's

3.0 star property
Bed & breakfast in Woodstock with free breakfast

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Photo gallery for Stay At Jimmy's

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

Reviews

10 out of 10
Exceptional

Popular amenities

  • Air conditioning
  • Pet-friendly
  • Kitchen
  • Parking included
  • Free WiFi
The current price is €194
includes taxes & fees
12 May - 13 May

Room options

View all photos for Signature Suite, Garden View

Signature Suite, Garden View

Signature Suite, Garden View

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

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

Highlights

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

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 - 13 min walk - 1.1 km
  • Billings Farm and Museum - 16 min walk - 1.4 km
  • Woodstock Country Club - 3 min drive - 1.9 km
  • Quechee Gorge Bridge - 12 min drive - 11.3 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

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 rooms are individually furnished, and boast comforts such as laptop-friendly workspaces and air conditioning, in addition to perks such as free WiFi.
More amenities include:
  • Bathrooms with rainfall showers or Jetted bath plus bidets and hairdryers
  • 55-inch Smart TVs with Netflix, Hulu and streaming services
  • Private gardens, wardrobes/cupboards and kitchenettes

Languages

Afrikaans, English, Spanish

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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 of normal check-in hours will receive an email with special check-in instructions and an access code; your host will greet you

Access methods

Access code, host will greet you

Pets

Pets are 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

Payment types at the property

Important information

Optional extras

  • Pet fee: USD 75 per accommodation, per stay (maximum USD75 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

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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

We should mention

This property does not have any lifts
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 3 May 2025, prices found for a 1-night stay for 2 adults at Stay At Jimmy's on 12 May 2025 start from €193.76, 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.

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?

Checkout 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. 29 out of 29 reviews
Rating 8 - Good. 0 out of 29 reviews
Rating 6 - Okay. 0 out of 29 reviews
Rating 4 - Poor. 0 out of 29 reviews
Rating 2 - Terrible. 0 out of 29 reviews

10/10

Cleanliness

10/10

Staff & service

10/10

Amenities

10/10

Property conditions & facilities

10/10

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

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

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

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

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

Zachary

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

New B&B in VT

Great hosts and very comfortable room.
Stayed 1 night in Apr 2024

10/10 Excellent

John

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

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

MacKenzie

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

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

Lois

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

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!
Stayed 1 night in Apr 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

Haeden

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

kathryn

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

Winnett

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

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

Daniele

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

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

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

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

Patricia

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

Randy

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