Stay At Jimmy'S Woodstock Exterior photoStay At Jimmy'S Woodstock Exterior photoStay At Jimmy'S Woodstock Exterior photo
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From349US$ /night
Check-in
19Apr2026Select date
Check-out
20Apr2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

45 Pleasant Street, Woodstock, Vermont, United States, VT 05091
-
Close to the city center
Perfect
9.4
10.0
/10
5.0
/5

Accommodations

Stay At Jimmy's offers a selection of 11 distinctive guest rooms, each equipped with personal seating areas and private bathrooms. Guests can enjoy amenities such as DVD players and flat-screen televisions in the well-appointed spaces. Many rooms come with additional features like kitchenettes for in-room snacks and meals.

Dining

The hotel includes an on-site restaurant, providing guests with accessible dining options throughout their stay. Breakfast is served daily and features locally sourced ingredients to enhance the experience. Additionally, the outdoor kitchen is available for guests to prepare their meals in a scenic setting.

Location

Situated in the scenic town of Woodstock, Stay At Jimmy's is surrounded by numerous hiking trails and cultural attractions. Guests can explore local art galleries, boutiques, and historic sites, all within a short distance from the hotel. The property is conveniently located near key landmarks, making it an accessible base for exploration.

Entertainment

Stay At Jimmy's offers a variety of entertainment options, including seasonal outdoor activities and gatherings. Guests can partake in social evenings filled with live music and community events. The surrounding area also hosts concerts and festivals, adding local flavor to the experience.

Wellness

The hotel emphasizes wellness with access to beautiful outdoor spaces for rejuvenating walks or meditation. In the nearby community, wellness classes in yoga and mindfulness are frequently offered. Additionally, the serene environment contributes to overall relaxation and tranquility.

Highlights

Location: Surrounded by hiking trails and art galleries

Accommodations: 11 distinctive guest rooms with kitchenettes

Dining: On-site restaurant with locally sourced ingredients

Entertainment: Seasonal outdoor activities and live music

Must-do experiences

  • Visit the Woodstock Museum for a deep dive into our music history.
  • Try the famous pancakes at The Garden Cafe for a local favorite.
  • Explore the scenic trails of Overlook Mountain for stunning views.
  • Attend a live music show at The Colony for an unforgettable night.
  • Check out the Sunday Farmers Market for fresh, local produce.
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Price and Room Availability Calendar

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Facilities

Stay At Jimmy'S offers amenities for your comfortable stay and unforgettable experiences

General

  • No smoking on site
  • Parking
  • Safe deposit box
  • Pets allowed
  • Security

Guest Parking

  • Cookware/ Kitchen utensils

Dining

  • In-room breakfast

Spa & Leisure

  • Garden area

Room features

  • Free Wi-Fi in rooms
  • 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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Stay At Jimmy'S 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
2400 ft
54 Pleasant St
Angkor Wat Restaurant
2200 ft
61 Pleasant St next to Sunoco
Amato's Express
2000 ft
66 Pleasant St
Ramunto's New York Pizza
1900 ft
433 Woodstock Rd Ste R4
Soulfully Good Cafe
3900 ft
67 Central St
Ruth's Table
1700 ft
61 Central St
The Daily Catch Woodstock
1700 ft
61 Central St
Mangalitsa
4100 ft
61 Central St Second floor
The Daily Catch
4100 ft
61 Central St
Mountain Creamery
4500 ft
33 Central St Ste 101
The Prince and the Pauper
4800 ft
24 Elm St
Explore Woodstock
Explore Woodstock
Top Attractions
Activities
Dining
Entertainment
Billings Farm Museum
Billings Farm Museum
25 minutes' walk
Historic farm museum showcasing dairy farming, animals, and interactive exhibits about Vermont's rural heritage.
Marsh-Billings
19 minutes' walk
A national park featuring beautiful trails, historic views, and the chance to learn about forest conservation efforts.
The Woodstock Gallery
The Woodstock Gallery
10 minutes' walk
Local art gallery featuring contemporary works by regional artists, offering a vibrant peek into the local art scene.
Fossil Glass
Fossil Glass
14 minutes' walk
Unique glass studio known for its exquisite fused glass art. Offers occasional workshops for hands-on experiences.
Hiking at Mount Tom
7 minutes' drive
Challenging hikes with breathtaking views for thrill-seekers, with several trails available for different skill levels.
Yoga at Heart Rock Kitchen
9 minutes' walk
Relaxing yoga sessions in a serene atmosphere, perfect for unwinding after a day of exploration.
Heart Rock Kitchen
Heart Rock Kitchen
9 minutes' walk
Charming eatery known for its fresh, locally-sourced ingredients and delightful brunch specials.
Angkor Wat Restaurant
Angkor Wat Restaurant
8 minutes' walk
Authentic Cambodian cuisine with flavorful dishes like curry and noodles, providing a cozy and inviting atmosphere.
Town Hall Theater
15 minutes' walk
Local theater featuring a variety of performances, including plays and concerts, with a warm, intimate vibe.
Woodstock Town Crier
Woodstock Town Crier
19 minutes' walk
Lively spot known for its live music events and local art showcases, perfect for enjoying an evening out.
Getting around
City Centre
Woodstock9 min  ·  2300 ft
Airports
Lebanon Municipal (LEB)37 min  ·  15.2 mi
Rutland State (RUT)91 min  ·  37.6 mi
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Property information and rules
Check-in
from 15:00-23:30
Check-out
until 11 am
Internet
Wireless internet is available in the hotel rooms 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.

Reviews and Ratings

Feedback about Stay At Jimmy'S from previous guests about their experience.
Review score
Based on 101 verified reviews
9.7/10
Perfect
97%
Recommend
Breakfast
7.5/10
Paid Wi-Fi
10.0/10
Guest reviews
based on 75 reviews
9.4/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
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FAQs
About Stay At Jimmy'S
What is the check-in and check-out policy at Stay At Jimmy's?
Check-in begins at 15:00 and check-out is required by 11:00.
Is parking available at Stay At Jimmy's?
Free private parking is available on-site without reservation.
What amenities are included in the rooms at Stay At Jimmy's?
Rooms feature air conditioning, a flat-screen TV, a kitchenette, and a private bathroom with a walk-in shower.
What dining options are available at Stay At Jimmy's?
A continental breakfast is served daily, with fresh pastries available.
Which nearby restaurants can guests visit while staying at Stay At Jimmy's?
Nearby dining options include Angkor Wat Restaurant and Ramunto's New York Pizza, both located 0.5 km away.
What is the distance from Stay At Jimmy's to Killington Mountain?
Stay At Jimmy's is located 38 km from Killington Mountain.
Does Stay At Jimmy's allow pets?
Pets are allowed at the property.
How far is Stay At Jimmy's from Lebanon Municipal Airport?
The hotel is located 23 km from Lebanon Municipal Airport.
What recreational activities are available near Stay At Jimmy's?
Guests can easily access Killington Mountain and Gifford Woods State Park for outdoor activities.
Is there free Wi-Fi available at Stay At Jimmy's?
Free Wi-Fi is available throughout the property.
Can guests enjoy views from their rooms at Stay At Jimmy's?
Rooms offer views of the garden.
What additional features does Stay At Jimmy's provide for guest comfort?
The hotel features a relaxing garden area and air-conditioned units with safety deposit boxes.

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Check-in
19Apr2026Select date
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Rooms and Guests2 Guests, 1 Room