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Stay At Jimmy's

3.0 star property
Bed & breakfast in Woodstock with free breakfast

Choose dates to view prices

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
  • Free Wi-Fi
  • Air-conditioning
  • Kitchen
The current price is ฿7,782
฿8,560 total
includes taxes & fees
22 Jan - 23 Jan

Room options

View all photos for Signature Double Room, Courtyard View

Signature Double Room, Courtyard View | Individually decorated, individually furnished, laptop workspace

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 | Individually decorated, individually furnished, laptop workspace

Signature Double Room, Garden View

9.0 out of 10
Wonderful
(2 reviews)

Highlights

Garden
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 | Individually decorated, individually furnished, laptop workspace

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
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
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About the area

Woodstock is home to Stay At Jimmy's. Killington Resort and Green Mountain Rock Climbing Center are worth checking out if an activity is on the agenda, while those in the mood for shopping can visit Quechee Gorge Village and King Arthur Baking Company. Red Wagon Toy Company and Billings Farm and Museum are also worth visiting. Visit our Woodstock travel guide
View more B&B in Woodstock
Map
45 Pleasant St, Woodstock, VT, 05091

What's nearby

  • When visiting Woodstock, Vermont, one not-to-miss outdoor attraction is the Marsh - Billings - Rockefeller National Historical Park, the first National Park in Vermont. The site is full of ambient trails with different atmospheres, whether you want to summit a mountain, run through a field or picnic on a lovely lake. Here you see The Pogue, a 14-acre (6-hectare) lake, featuring mountain reflections and beautiful Great Blue herons hungry for bass fish. For me, this spot was pure heaven in Vermont. #travel #AmazonDestinations #spon
    Marsh-Billings-Rockefeller National Historical Park
    11 min walk - 1.0 km
  • Billings Farm and Museum, Woodstock Vermont USA
    Billings Farm and Museum
    16 min walk - 1.4 km
  • Red Wagon Toy Company
    8 min walk - 0.7 km
  • Woodstock Town Hall Theatre
    15 min walk - 1.3 km
  • Woodstock Country Club
    2 min drive - 1.8 km

Getting around

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

Restaurants

  • Dunkin'
    11 min drive
  • Simon Pearce Restaurant, Retail & Glassblowing
    11 min drive
  • Mon Vert Cafe
    6 min walk
  • The Public House
    13 min drive
  • Cumberland Farms
    6 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

Similar properties

Interior
The Vesper
  • Breakfast included
  • Parking included
  • Free Wi-Fi
  • Air-conditioning
9.2 out of 10, Wonderful, 53 reviews
The price is ฿5,801
฿6,382 total
includes taxes & fees
25 Jan - 26 Jan
The Vesper

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
  • Limited on-site self parking
  • 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
Information provided by the property may be translated using automated translation tools

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

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

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 20 Jan 2026, prices found for a 1-night stay for 2 adults at Stay At Jimmy's on 22 Jan 2026 start from ฿7,782.0, 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?

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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Reviews

Stay At Jimmy's Reviews

10

Exceptional

10

Cleanliness

10

Amenities

10

Staff & service

10

Property conditions & facilities
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

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

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

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

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

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

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

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

Erin

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

10/10 Excellent

Julie

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

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.
Stayed 1 night in Aug 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

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

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

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

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

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

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

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

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

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

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

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

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

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

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