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From349US$ /night
Check-in
31Dec2025Select date
Check-out
01Jan2026Select 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
9.5
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 combines private accommodations with self-catering convenience. Stay At Jimmy'S features air-conditioned double rooms equipped with private bathrooms containing walk-in showers and spa baths. Each unit includes a fully-equipped kitchenette with a refrigerator, microwave, coffee maker, and essential cookware. The rooms offer flat-screen TVs with streaming services, safety deposit boxes, and wardrobes. A continental breakfast is served daily, and guests have access to a private terrace overlooking the garden. The property provides free WiFi and complimentary private parking. Within 0.5 miles, guests can visit Dana House, Gallery One On The Green, and Artemis Global Art, while Billings Farm Museum lies 1 mile away. Eight restaurants, including Angkor Wat Restaurant and Ramunto's New York Pizza, are situated within 1 mile of the property.

Pros

Private entrance for each unit ensures independent access

Hot tub and spa bath available in double rooms

Garden views from personal terraces

Located within walking distance of 8 diverse dining options

Cons

14.5 miles from Lebanon Municipal Airport

Limited on-site dining options beyond breakfast

“If you're visiting Woodstock, this is a place to consider. The combination of kitchenettes and garden views sets it apart, particularly for longer stays or those needing pet-friendly accommodation. The location is ideal for exploring both the town and nearby outdoor attractions, a genuine Vermont experience.”
Hotel logo
Isabella MooreSenior Editorial Director at Petfriendlyhotels
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Select your room type

Cozy rooms, spacious suites, and family-friendly homes, all with flexible cancellation policies & 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

Check availability and rates for your selected dates!

Facilities

Enjoy premium amenities for a relaxing stay with your pet

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
25 minutes' walk
A working dairy farm and museum showcasing Vermont's rural heritage with farm animals, interactive exhibits, and seasonal events.
Marsh - Billings
19 minutes' walk
A scenic national park featuring hiking trails and a historic mansion, perfect for nature lovers and history enthusiasts.
The Woodstock Gallery
10 minutes' walk
An art gallery highlighting local artists, with rotating exhibits and unique pieces, making it a cultural spot in town.
Fossil Glass
14 minutes' walk
A glassblowing studio where visitors can watch artisans create beautiful glass art, offering workshops for a hands-on experience.
Hiking Mount Tom
45 minutes' walk
A challenging hike providing stunning views of the area. Perfect for thrill-seekers, accessible via well-marked trails.
Yoga at Collective
16 minutes' walk
A cozy studio offering various yoga classes for all levels, promoting relaxation and wellness in a tranquil setting.
Kayaking on the Ottaquechee River
10-minute drive
Kayak rentals available for a peaceful day on the river, perfect for families and solo adventurers during the warmer months.
Heart Rock Kitchen
9 minutes' walk
Cozy atmosphere with a menu of local specialties and inventive dishes, featuring local ingredients. Reservations recommended.
Angkor Wat Restaurant
8 minutes' walk
Authentic Cambodian cuisine in a casual setting, known for its flavorful curries and vegetarian-friendly options.
Ramunto's New York Pizza
7 minutes' walk
Offering delicious New York-style pizza with a family-friendly atmosphere, perfect for casual dining with kids.
Town Hall Theater
15 minutes' walk
A historic venue hosting live performances, films, and community events, creating a vibrant local arts scene for everyone.
Woodstock Town Crier
19 minutes' walk
A lively community hub featuring local news, events, and a great place for socializing and enjoying live music.
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
How far is Stay At Jimmy's from Killington Mountain?
The hotel is located 38 km from Killington Mountain.
What time can I check in and check out at Stay At Jimmy's?
Check-in is at 15:00 and check-out is at 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 coffee machine, a refrigerator, a microwave, and a private bathroom with a walk-in shower.
Is there any dining option available at Stay At Jimmy's?
A continental breakfast is served daily, and guests can enjoy in-room breakfast.
Are pets allowed at Stay At Jimmy's?
Pets are allowed at the hotel.
What services does Stay At Jimmy's provide for guests?
Guests can access free Wi-Fi and relax in the garden.
How far is the nearest airport from Stay At Jimmy's?
Lebanon Municipal Airport is located 23 km from the hotel.
What nearby attractions are accessible from Stay At Jimmy's?
Attractions include Mount Tom, located 2 km away, and Gifford Woods State Park, 34 km away.
What nearby restaurants can guests enjoy while staying at Stay At Jimmy's?
Options include Angkor Wat Restaurant and Ramunto's New York Pizza, both 0.5 km away.

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