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Stay At Jimmy's

3.0 star property

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Photo gallery for Stay At Jimmy's

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

Reviews

10 out of 10
Exceptional

Popular amenities

  • Parking included
  • 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)
    ‪40 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
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

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
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

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
(3 reviews)
  • Garden view
  • 470 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

About the neighborhood

Woodstock

Stay At Jimmy's places you within a 5-minute walk of Mt Ascutney Hospital and Health Center Primary Care - Woodstock and Ottauquechee Health Center. This 3-room, 3-star bed & breakfast has free breakfast, free in-room WiFi, and free self parking.
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
  • Middle Covered Bridge - 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

Getting around

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

Restaurants

  • ‪Cumberland Farms - ‬6 min walk
  • ‪Simon Pearce Restaurant, Retail & Glassblowing - ‬11 min drive
  • ‪The Red Rooster - ‬11 min walk
  • ‪Worthy Kitchen - ‬13 min walk
  • ‪Dunkin' - ‬11 min drive

About this property

Stay At Jimmy's

Guests of Stay At Jimmy's enjoy features like free WiFi in public areas. Free parking is available if you drive. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls.
55-inch Smart TVs come with digital channels and Netflix, and guests can stay connected with free WiFi. Along with relaxing touches like rainfall showers and jetted tubs, bathrooms offer hair dryers and slippers. Other amenities include kitchenettes, private yards, and microwaves. Housekeeping is available on request.

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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

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

Renovations and closures

This property is closed from November 1 2026 to March 22 2028 (dates subject to change).

Access methods

Access code, host will greet you

Pets

  • This property welcomes pets for USD 75 per accommodation, per stay (maximum USD 75 per stay)
  • Food and water bowls are available
  • Service animals exempt from fees

Children and extra beds

  • This property doesn't allow children 18 and younger (only guests older than 18 are allowed)

Property payment types

Important information

Optional extras

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

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

This list may not be comprehensive. Fees and deposits might 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
  • Check-in: 3:00 PM—-11:30 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 21
Driving? This property offers free parking.

We should mention

Details about charges, deposits, or other important information:

  • 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.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • This property accepts credit cards and debit cards. Cash is not accepted. 

Additional information about polices, regulations, and more:

  • There are no elevators.

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 a free cancellation option available at Stay At Jimmy's?

Stay At Jimmy's provides free cancellation on select room rates. If you'd like to learn more, take a look at the cancellation policy on Orbitz.

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

As of Jul 3, 2026, prices found for a 1-night stay for 2 adults at Stay At Jimmy's on Jul 5, 2026 start from $274, 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.

What can I see within easy reach of Stay At Jimmy's?

This bed & breakfast in Woodstock is within a 10-minute walk of Red Wagon Toy Company, Billings Park and Trail, and Dana House Museum. You'll also find Marsh-Billings-Rockefeller National Historical Park and Woodstock Town Hall Theatre less than a mile away.

Will I be able to park at Stay At Jimmy's?

Yes, uncovered self parking is offered for free at the bed & breakfast. Wheelchair-accessible van parking is also available for guests.

Does Stay At Jimmy's include a casino?

No, Stay At Jimmy's doesn't have a casino.

Is there an indoor pool at Stay At Jimmy's?

No, there is no indoor pool at this bed & breakfast.

Is Stay At Jimmy's a good place to stay for couples?

Amenities that appeal to couples at this bed & breakfast include a jetted bathtub, Hulu, and a kitchenette.

Does Stay At Jimmy's have a hot tub?

No, but this bed & breakfast offers jetted bathtubs in all guestrooms.

Does Stay At Jimmy's have a restaurant that serves breakfast?

Stay At Jimmy's offers free continental breakfast each morning though there is no restaurant.

Does Stay At Jimmy's allow pets to stay for free?

Although they can't stay for free, pets are welcome at Stay At Jimmy's for a fee of USD 75 per accommodation, per stay. The property also provides food and water bowls.

Does Stay At Jimmy's have connecting rooms available?

No, there aren't connecting guestrooms at this bed & breakfast.

What is the closest airport to Stay At Jimmy's?

The closest major airport to Stay At Jimmy's is Lebanon, NH (LEB-Lebanon Municipal), which is 15.1 mi away (21 minutes by car). Another top airport is Springfield, VT (VSF-Hartness State), which is located 22.8 mi away (34-minute drive).

Can I book a room with a balcony at Stay At Jimmy's?

No, there aren't any guestrooms at Stay At Jimmy's that offer a balcony.

Stay At Jimmy's Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 48 out of 49 reviews
Rating 8 - Good. 1 out of 49 reviews
Rating 6 - Okay. 0 out of 49 reviews
Rating 4 - Poor. 0 out of 49 reviews
Rating 2 - Terrible. 0 out of 49 reviews

10/10

Cleanliness

10/10

Staff & service

10/10

Amenities

10/10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Heather

Liked: Cleanliness, amenities, property conditions & facilities
Wonderful amenities, location, and team, Highly recommend and would love to stay again
Stayed 1 night in Oct 2025
Verified

10/10 Excellent

Meghan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We've stayed at Jimmy's a couple of times and have had great experiences both visits. Highly recommend if you're in the Woodstock area!
Stayed 2 nights in Feb 2026
Verified

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
Verified

10/10 Excellent

Scott

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

10/10 Excellent

michael

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very cool space- a lottle unorthodox, but so much the better!
Stayed 1 night in Mar 2026
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

10/10 Excellent

Haeden

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

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