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From349US$ /night
Check-in
14Dec2025Select date
Check-out
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Rooms and Guests2 Guests, 1 Room
Key details

Hotel Details

45 Pleasant Street, Woodstock, Vermont, United States, VT 05091
-
Close to The Woodstock Gallery
Perfect
9.6
9.9
/10
5.0
/5

Stay At Jimmy'S - A Garden-View B&B with Hot Tub, Private Terrace, and Full Kitchenette

Located 1.5 miles from Mount Tom, this Woodstock hotel features air-conditioned rooms with private terraces overlooking the garden. Stay At Jimmy'S provides free private parking and complimentary WiFi throughout the property. Each unit at Stay At Jimmy's includes a fully equipped kitchenette with a refrigerator, microwave, coffee maker, and essential cookware. The spacious double rooms offer private entrances, walk-in showers, and flat-screen TVs with streaming services. A continental breakfast is served daily. A hot tub and spa bath are available for guest relaxation, along with access to the property's garden. The B&B sits within walking distance of Norman Williams Public Library and Artemis Global Art (0.5 miles), while Fossil Glass is 0.5 miles away. Popular dining options within 0.5 miles include The Daily Catch, Mangalitsa, and Soulfully Good Cafe.

Pros

Private entrance for each unit ensures independent access

Walking distance to 8 restaurants within 1 mile

Garden views from every terrace

Located 0.5 miles from cultural attractions

Cons

14.5 miles from Lebanon Municipal Airport

21 mile from Gifford Woods State Park

“This Woodstock B&B strikes me as particularly well-suited to travelers seeking a blend of independence and attentive service, given the combination of kitchenettes and included breakfast. I was especially impressed by the reported attention to detail and the pet-friendly environment, an advantage for those traveling with animals. For a relaxing and convenient stay in a walkable town, it seems like a very good option.”
Hotel logo
James DavidEditor-in-Chief at Hotelsdowntown
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Select room type

Choose from double rooms, family suites, and premium stays. Enjoy breakfast, flexible cancellations, and exclusive deals.
King Room Disability Access
2 persons
17 m² 
1 King-size bed
Shower
Coffee machine
King Room Garden View
2 persons
16 m² 
1 King-size bed
Shower
Coffee machine
King Room Spa Bath
2 persons
44 m² 
1 King-size bed
Shower
Coffee machine

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Facilities

Hotel has comfortable rooms, premium services, and a prime downtown location

General

  • No smoking on site
  • Free Wi-Fi
  • Parking
  • Safe deposit box
  • Pets allowed
  • Security

Guest Parking

  • Cookware/ Kitchen utensils

Dining

  • In-room breakfast

Spa & Leisure

  • Garden area

Room features

  • Air conditioning
  • Heating
  • Sitting area
  • Patio
  • Terrace
  • Tea and coffee facilities

Bathroom

  • Free toiletries

Self-catering

  • Cookware/ Kitchen utensils

Media

  • Flat-screen TV

Room decor

  • Parquet floor
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Location

45 Pleasant Street, Woodstock, Vermont, United States, VT 05091
Map view
45 Pleasant Street, Woodstock, Vermont, United States, VT 05091
Restaurants
Heart Rock Kitchen
710 m
54 Pleasant St
Angkor Wat Restaurant
650 m
61 Pleasant St next to Sunoco
Amato's Express
590 m
66 Pleasant St
Ramunto's New York Pizza
560 m
433 Woodstock Rd Ste R4
Soulfully Good Cafe
1.2 km
67 Central St
Ruth's Table
500 m
61 Central St
The Daily Catch Woodstock
510 m
61 Central St
Mangalitsa
1.2 km
61 Central St Second floor
The Daily Catch
1.2 km
61 Central St
Mountain Creamery
1.4 km
33 Central St Ste 101
The Prince and the Pauper
1.5 km
24 Elm St
Explore Woodstock
Explore Woodstock, VT
Top Attractions
Activities
Dining
Entertainment
The Woodstock Gallery
10 minutes' walk
A local art gallery featuring regional artists. Regular exhibitions and community events make it a vibrant cultural stop.
Billings Farm Museum
25 minutes' walk
A working farm and museum showcasing Vermont's agricultural heritage. Offers guided tours and interactive exhibits.
Marsh - Billings
19 minutes' walk
This historic site blends nature with art and culture, featuring beautiful trails and gardens for a leisurely stroll.
Fossil Glass
14 minutes' walk
An intriguing glassblowing studio where you can watch artisans at work. Unique pieces available for purchase on-site.
Outdoor Hiking at Mount Tom
7 minutes' drive
Challenging hiking trails offering stunning views of the area. Perfect for outdoor enthusiasts looking for an adventure.
Relaxation at Soulfully Good Cafe
14 minutes' walk
A cozy spot for relaxing with organic, healthy dishes and smoothies. A great place for breakfast or a midday break.
Heart Rock Kitchen
9 minutes' walk
Warm, rustic atmosphere featuring a menu of American cuisine with a twist. Reservations recommended for weekend dining.
Angkor Wat Restaurant
8 minutes' walk
Exquisite Cambodian dishes with vibrant flavors. Casual dining perfect for families and vegetarian-friendly options.
Town Hall Theater
15 minutes' walk
Charming venue hosting live performances, films and events. Offers programs for all ages and a rich community vibe.
Middle Covered Bridge
10 minutes' walk
Iconic historical site perfect for family photos or a scenic stroll. Picturesque views year-round attract many visitors.
Getting around
City Centre
Woodstock9 min  ·  700 m
Airports
Lebanon Municipal Airport (LEB)37 min  ·  24.4 km
Rutland State Airport (RUT)91 min  ·  60.5 km
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Property information and rules
Check-in
from 15:00-23:30
Check-out
until 11 am
Internet
is available in for free.
Breakfast
At the hotel Stay At Jimmy'S guests are invited to a full breakfast served for free. 
Pets
Pets are allowed on request.
FAQs
About Stay At Jimmy'S
What is the distance from Stay At Jimmy's to Killington Mountain?
The hotel is located 38 km from Killington Mountain.
How far is Stay At Jimmy's from Lebanon Municipal Airport?
Lebanon Municipal Airport is 23 km away from the hotel.
What amenities are provided in the rooms at Stay At Jimmy's?
Rooms are equipped with air conditioning, a flat-screen TV, a coffee machine, a microwave, a fridge, and a safety deposit box.
Is there free Wi-Fi available at Stay At Jimmy's?
Free Wi-Fi is available throughout the property.
What breakfast options are available at Stay At Jimmy's?
The hotel serves fresh pastries, fruits, and juice for breakfast.
Does Stay At Jimmy's offer private parking?
Free private parking is available on-site.
What are the check-in and check-out times at Stay At Jimmy's?
Check-in is at 15:00 and check-out is at 11:00.
Are pets allowed at Stay At Jimmy's?
Pets are allowed at the hotel.
What nearby restaurants can guests find close to Stay At Jimmy's?
Nearby restaurants include Angkor Wat Restaurant and Ramunto's New York Pizza, both 0.5 km away.
What recreational options does Stay At Jimmy's provide?
Guests can enjoy a garden and patio area at the hotel.
Does Stay At Jimmy's feature kitchenette facilities in the rooms?
Rooms include kitchenette facilities equipped with a refrigerator, microwave, and kitchenware.
Are there any attractions near Stay At Jimmy's?
Mount Tom is located 1 km from the hotel and Gifford Woods State Park is 34 km away.
What type of guests does Stay At Jimmy's cater to?
The hotel targets families looking for a relaxing getaway and outdoor enthusiasts visiting for hiking or skiing.

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