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9.8 / 10 Guest Rating

Stay At Jimmy's

45 Pleasant Street, Woodstock, us

Stay At Jimmy's - main view

About the Property

Charming Accommodation near Nature
Explore the beauty of Woodstock while staying at Stay At Jimmy's. Enjoy the comfort and convenience of a kitchenette, patio, and free WiFi during your stay.

Cozy and Well-Equipped Units
Experience a comfortable stay with air-conditioned rooms equipped with modern amenities like a flat-screen TV, microwave, and private bathroom. Some units even feature a private entrance for added privacy.

Relaxing Garden and Scenic Views
Start your day with a delicious continental breakfast and unwind in the garden with picturesque garden views. Just a short distance from Dartmouth College and Gifford Woods State Park.

Book now for a memorable stay at Stay At Jimmy's.

Facilities & Amenities

WiFi available
Free WiFi
Parking
Free Parking
Air conditioning
Heating
Terrace
Garden
Pets allowed
Breakfast in the room

Important Information

Check-in & Out

Check-in
Check-out11:00 AM

Property Notes

- Complimentary breakfast is provided to guests, consisting of fresh pastries, juices, coffee, tea, and snack bars. - Breakfast is served in-room daily.Managed by a private host A deposit may be required at the property.

Check Room Availability

1 night · 2 adults

No rooms available

We couldn't find any available rooms for these dates and guests. Try adjusting your search criteria.

Guest Reviews

9.8
Exceptional103 verified reviews
AI Summary

Guests highly rate the great service and frequently praise the cozy rooms.

Categories

Cleanliness9.6
Service10.0
Location10.0
Room Quality10.0
Amenities10.0
Value for Money9.6
Food and Beverage9.2
Overall Experience10.0

Select topics to read reviews

J
JeffusUS
Verified booking
couple
Standard Room
Stayed in Oct 28, 2025

"Wonderfully decorated and comfortably appointed - plus warm hospitality and delicious pastries!"

10.0
Helpful?
M
MiriamusUS
Verified booking
couple
Standard Room
Stayed in Oct 13, 2025

"This place should be at the top of your list of places to stay in Woodstock, VT."

10.0

Everything, the owners are so thoughtful with every detail and so incredibly kind/helpful.

We loved everything!

Helpful?
C
ClaudiaatAT
Verified booking
couple
Standard Room
Stayed in Oct 13, 2025

"Zentrale, aber zu teure Unterkunft in Woodstock"

6.0

Die Lage im Zentrum von Woodstock, VT ist gut. Gut ausgestattete Snackbar. Komfortables Badezimmer. Veranda auf der Rückseite des Hauses. Sauberkeit passt! Alles ist liebevoll eingerichtet.

Maßlos überteuert! Croissants und Muffins für das Frühstück waren schon am Anreisetag im Zimmer (unter einer Glasglocke), es hat die Hälfte der auf der Homepage angekündigten Dinge für das Frühstück gefehlt (Breads, Fruit & Juices). Im Zimmer Chill frühstückt man auf einer Couch mit niedrigem Glastisch, sehr unbequem. So hip, wie angekündigt, ist es nicht.

Helpful?
N
NickusUS
Verified booking
couple
Standard Room
Stayed in Oct 12, 2025

"Exceptional"

10.0
Helpful?
E
Erin
Verified booking
Standard Room
Stayed in Oct 7, 2025

"Exceptional"

10.0

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!

Helpful?
G
GarygbGB
Verified booking
couple
Standard Room
Stayed in Oct 6, 2025

"Super cool stay in the heart of beautiful Woodstock, VT"

10.0

We stayed in the suite and it was such a lovely space to base ourselves in for a few days. Great location, super clean and modern with very cool interior. Having treats like cookies, muffins etc.. provided was such a nice touch. Jimmy and John obviously care very much for their customers they looked after us like royalty. Wouldn't hesitate to book again.

Helpful?
C
Catherine
Verified booking
Standard Room
Stayed in Oct 2, 2025

"Exceptional"

10.0

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.

Helpful?
L
LisausUS
Verified booking
couple
Standard Room
Stayed in Sep 30, 2025

"Quaint, well-appointed property and fabulous hosts in an idyllic setting-what more can you ask for!"

10.0

Stay at Jimmy's is a fabulous place to stay. It far exceeded our expectations and both John and Jimmy were excellent hosts. They made us feel at home. The regular complimentary amenties at this property are way beynond what you would receive at a normal, high-end hotel. The property has a quaint wrap around porch where we sat in the evening and Jimmy even lent us his portable speaker so we could play our own music. It was our favorite place to stay amongst all the places we visited on our 2-week New Englend Autumn trip. The village of Woodstock, Vermont is by far the most quaint and beautiful small town we've ever visited in America and the Stay at Jimmy's was the frosting on the cake!

Nothing could have been better. It was all fabulous!

Helpful?
N
NickyusUS
Verified booking
couple
Standard Room
Stayed in Sep 20, 2025

"Lovely stay In Vermont"

10.0

The room was beautifully decorated and furnished with tons of thoughtful touches. they thought of everything you could ever need and things you might not need, but made the stay even nicer. We were supplied with ample drinks and snacks. Very impressed and would definitely recommend!

Nothing

Helpful?
R
ronitilIL
Verified booking
couple
Standard Room
Stayed in Sep 10, 2025

"Exceptional"

9.0

ג’מי עשה כל שביכולתו כדי שנרגיש בנוח ,לאחר שהייתה אי הבנה לגבי ארוחת הבוקר הוא נתן לנו אפשרות לאכול על חשבונם במסעדה מתאימה .מאד מעריכה זאת .תודה

חסר מקום אחסון לחפצים האישיים

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