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From349US$ /night
Check-in
11Jan2026Select date
Check-out
12Jan2026Select 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
9.9
/10
5.0
/5

Location

Stay At Jimmy's is located in the heart of Woodstock, just steps away from the historic attractions and vibrant arts community of the town. Guests can enjoy proximity to local shops, galleries, and restaurants, all within walking distance. The hotel offers convenient access to various hiking trails and outdoor activities in the nearby Catskill Mountains.

Accommodations

The hotel offers eight spacious guest rooms, each uniquely decorated to reflect the character of the surrounding area. Accommodations include a mix of queen and king-sized beds, providing a restful night's sleep for all guests. Each room features air-conditioning and en-suite bathrooms, ensuring comfort during the stay.

Dining

Stay At Jimmy's includes a complimentary breakfast served daily, allowing guests to start their day with a variety of options. The hotel's on-site café offers a selection of fresh pastries and local coffee. Guests can also explore nearby dining options that highlight local cuisine and flavors.

Wellness

The hotel offers access to complimentary yoga classes at a nearby studio, promoting relaxation and wellness during the stay. Guests can unwind in the spacious garden area, an inviting space for meditation or reading. Local wellness services also include massage therapy available in town.

Entertainment & Activities

Stay At Jimmy's provides guests with bicycles for rent, encouraging exploration of the picturesque surroundings. The hotel hosts seasonal events, enhancing the experience with local music and art. Guests can take advantage of nearby outdoor activities like hiking and kayaking.

Highlights

Location: Heart of Woodstock, close to historic attractions

Rooms: Eight uniquely decorated guest rooms

Dining: Complimentary breakfast served daily

Wellness: Access to yoga classes and local wellness services

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.
View all

Select your room type

The hotel offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special 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

Price and Room Availability Calendar

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Facilities

The hotel offers amenities for your comfortable stay and unforgettable experiences

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

  • 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
Show more

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
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  ·  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 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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