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Stay At Jimmy's

3.0 star property
Enjoy the free WiFi at this 3-star Woodstock B&B

Choose dates to view prices

Photo gallery for Stay At Jimmy's

Front of property
Signature Double Room, Courtyard View | Individually decorated, individually furnished, laptop workspace
Signature Suite, Garden View | Individually decorated, individually furnished, laptop workspace
Signature Double Room, Garden View | Individually decorated, individually furnished, laptop workspace
Front of property

Reviews

10 out of 10
Exceptional

Popular amenities

  • Pet friendly
  • Free WiFi
  • Air conditioning
  • Kitchen

Explore the area

View in a map
45 Pleasant St, Woodstock, VT, 05091
  • Place, Red Wagon Toy Company
    ‪8 min walk‬
  • Place, Woodstock Town Hall Theatre
    ‪15 min walk‬
  • Place, Billings Farm and Museum
    ‪16 min walk‬
  • Airport, Springfield, VT (VSF-Hartness State)
    ‪39 min drive‬

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)
  • 180 sq ft
  • 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)
  • Garden view
  • 177 sq ft
  • 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)
  • Garden view
  • 470 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

About the neighborhood

Woodstock

In Woodstock .Within a 5-minute walk of the B&B, you'll find 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 half a mile (1 km).
View more B&B in WoodstockOpens in a new window

What's nearby

  • Red Wagon Toy Company - 8 min walk - 0.5 miles
  • Marsh-Billings-Rockefeller National Historical Park - 11 min walk - 0.6 miles
  • Woodstock Town Hall Theatre - 15 min walk - 0.8 miles
  • Billings Farm and Museum - 16 min walk - 0.9 miles
  • Woodstock Country Club - 2 min drive - 1.2 miles

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

Enjoy the free WiFi at this 3-star Woodstock B&B
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 slippers and hair dryers. Each accommodation is individually furnished and decorated. Accommodations at this 3-star bed & breakfast have kitchenettes with microwaves and cookware/dishes/utensils. Bathrooms include bathtubs or showers with jetted bathtubs and rainfall showerheads, and bidets.

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

Similar properties

Interior
The Vesper
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
4.6 out of 5, Wonderful, 55 reviews
$179 nightly
The price is $197
Feb 10 - Feb 11
Total with taxes and fees
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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

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

Entertainment

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

Bathroom

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

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
Information provided by the property may be translated using automated translation tools

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.

Property 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 USD 75 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, 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
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, 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 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

How close is Stay At Jimmy's to the airport?

Stay At Jimmy's is 15.1 mi (21-min drive) away from the Lebanon, NH (LEB-Lebanon Municipal) airport, the closest popular airport to the property.

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

As of Jan 30, 2026, prices found for a 1-night stay for 2 adults at Stay At Jimmy's on Feb 1, 2026 start from $299.0, 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.

Does Stay At Jimmy's have an airport shuttle?

Airport shuttle services are not available at Stay At Jimmy's.

Does Stay At Jimmy's offer free breakfast?

Stay At Jimmy's offers free continental breakfast every day from 7:00 AM to 9:00 AM.

Is there a casino at Stay At Jimmy's?

No, there is no casino at this bed & breakfast.

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

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

Is there free parking at Stay At Jimmy's?

This bed & breakfast offers free self parking.

Does Stay At Jimmy's have a pool?

Stay At Jimmy's does not have a pool.

Does Stay At Jimmy's have a spa?

There are no spa services available at this bed & breakfast.

How close is Stay At Jimmy's to downtown Woodstock?

Stay At Jimmy's is 0.4 mi away from Woodstock.

Stay At Jimmy's Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 46 out of 47 reviews
Rating 8 - Good. 1 out of 47 reviews
Rating 6 - Okay. 0 out of 47 reviews
Rating 4 - Poor. 0 out of 47 reviews
Rating 2 - Terrible. 0 out of 47 reviews

10/10

Cleanliness

10/10

Staff & service

10/10

Amenities

10/10

Property conditions & facilities

Reviews

10/10 Excellent

CLARA

Traveled with partner
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

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

Catherine

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
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.
Our room, the hangout ♥️
Halloween
Back porch
Front of property
Stayed 2 nights in Sep 2025

10/10 Excellent

Ayeola

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

Julie

Traveled with family
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

Stephen

Stayed 2 nights in Jul 2025

10/10 Excellent

Gary, saratoga springs

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

8/10 Good

Kathryn Ann

Traveled with partner
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

Scott

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

10/10 Excellent

Benjamin

Traveled with partner
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

Traveled with partner
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

Traveled with group
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

Traveled with partner
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

Thomas, Merrimack

Traveled with family
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

Sandra

Traveled with partner
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

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

Traveled 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

Patricia

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

10/10 Excellent

Dennis

Traveled 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