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Stay At Jimmy's

3.0 star property
Bed & breakfast in Woodstock with free breakfast

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Front of property
Front of property
Signature Double Room, Garden View | 1 bedroom, individually decorated, individually furnished
Signature Double Room, Courtyard View | 1 bedroom, individually decorated, individually furnished
Signature Double Room, Courtyard View | 1 bedroom, individually decorated, individually furnished

Reviews

10 out of 10
Exceptional

Popular amenities

  • Pet friendly
  • Air conditioning
  • Kitchen
  • Parking included
  • Free WiFi

Explore the area

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

Room options

View all photos for Signature Double Room, Courtyard View

Signature Double Room, Courtyard View | 1 bedroom, individually decorated, individually furnished

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 | 1 bedroom, individually decorated, individually furnished

Signature Double Room, Garden View

9.0 out of 10
Wonderful
(2 reviews)
  • 177 sq ft
  • Sleeps 2
  • 1 King Bed

View all photos for Signature Suite, Garden View

Signature Suite, Garden View | 1 bedroom, individually decorated, individually furnished

Signature Suite, Garden View

10.0 out of 10
Exceptional
(2 reviews)
  • 470 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

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.
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What's nearby

  • Marsh-Billings-Rockefeller National Historical Park - 13 min walk - 0.7 miles
  • Woodstock Town Hall Theatre - 15 min walk - 0.8 miles
  • Billings Farm and Museum - 16 min walk - 0.9 miles
  • Woodstock Country Club - 3 min drive - 1.2 miles
  • VINS Nature Center - 4 min drive - 1.4 miles

Getting around

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

Restaurants

  • ‪Cumberland Farms - ‬6 min walk
  • ‪The Skinny Pancake Quechee - ‬10 min drive
  • ‪The Public House - ‬13 min drive
  • ‪Simon Pearce Restaurant, Retail & Glassblowing - ‬11 min drive
  • ‪Dunkin' - ‬11 min drive

About this property

Stay At Jimmy's

Bed & breakfast in Woodstock with free breakfast
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.

Similar properties

Property grounds

The Shire Woodstock

  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
8.8 out of 10, Excellent, 841 reviews
$158 nightly
The price is $174
Nov 2 - Nov 3
Total with taxes and fees
The Shire Woodstock

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

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.

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. Accessible 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 u0026 breakfast include a jetted bathtub, a kitchenette, and Netflix.

Are there hot tubs at Stay At Jimmy's?

Yes, some guestrooms at this bed & breakfast feature private indoor spa tubs.

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.

Are there connecting rooms at Stay At Jimmy's?

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).

Are there rooms with balconies at Stay At Jimmy's?

No, there aren't any guestrooms with balconies at Stay At Jimmy's.

Stay At Jimmy's Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 42 out of 43 reviews
Rating 8 - Good. 1 out of 43 reviews
Rating 6 - Okay. 0 out of 43 reviews
Rating 4 - Poor. 0 out of 43 reviews
Rating 2 - Terrible. 0 out of 43 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

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

Jessica

Traveled 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

Traveled 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

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

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

Traveled 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

Traveled 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

Traveled with pets, Traveled with family
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

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