Entire home
The entire Stephentown Hotel! 28 person occupancy
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Photo gallery for The entire Stephentown Hotel! 28 person occupancy





Reviews
1010 out of 10
Exceptional
Entire home
Popular amenities
- Parking available
- Dryer
- Washer
- Pet-friendly
- Barbecue grill
- Kitchen
Explore the area

Stephentown, NY
- Zema's NurseryPlace, Zema's Nursery6 min drive
- Jiminy Peak Mountain ResortPlace, Jiminy Peak Mountain Resort17 min drive
- Tanglewood Music CenterPlace, Tanglewood Music Center37 min drive
- Pittsfield, MA (PSF-Pittsfield Municipal)Airport, Pittsfield, MA (PSF-Pittsfield Municipal)24 min drive
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About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
The entire Stephentown Hotel! 28 person occupancy
The listing is for the entire Stephentown Hotel! The building has (x4) private apartments consisting of: 10 Bedrooms, 6 Bathrooms, Sleeps 28! 2 private outdoor amenity spaces!!!
Welcome to the historic Stephentown Hotel! This unique property offers the entire building with four private apartments, each with its own entrance. Whether you`re planning a family reunion, a group ski trip, or a serene getaway, this space is perfect for up to 28 guests.
Accommodations:
- Total Capacity: 28 guests
- Bedrooms: 10 (4 King beds, 6 Queen beds, 2 pullout sofas, 2 regular couches)
- Bathrooms: 6
- Living Rooms: 5
- Kitchens: 4
- Arcade Rooms: 4 (one in every apartment)
- Outdoor Spaces: 2 private amenity areas with fire pits, BBQs, outdoor games, picnic tables, fire wood, fire starter and more.
Apartment Breakdown:
- Apartment 1 (1st FL): 2 Bedrooms (two Queen beds), 1 Bathroom, Living Room with 2 Sleeper Sofas, Large Eat-in Kitchen, Arcade. Capacity: 6 guests.
- Apartment 2 (1st FL): Studio Layout, 1 King Bed, 1 Queen Pullout Couch, 1 Sleeper Sofa, Eat-in Kitchen, Private Deck, Arcade. Capacity: 4 guests.
Apartment 3 (1st/2nd FL): Triplex with 5 Bedrooms, 3 Bathrooms, 2 Living Rooms, Large Eat-in Kitchen, Arcade, Private Washer/Dryer, Large Deck. Capacity: 12 guests.
Apartment 4 (2nd FL): 2 Bedrooms (King and Queen beds), 1 Bathroom, Living Room with Queen Pullout, Large Eat-in Kitchen, Arcade, Large Deck, Private Washer/Dryer. Capacity: 6 guests.
Amenities:
- Ductless AC units with individual remotes in every bedroom and living room.
- Two washer/dryer units available (in Apartments 3 and 4).
- Keurig machines, Smart TVs, blackout shades, and more in each apartment.
- Culligan water filtration system for fresh-tasting water throughout the building.
- S’mores goodie bags included for stays between May 1st and November 1st.
- fully furnished kitchens with pots, pans, utensils, and basic cooking supplies. Enjoy complimentary water bottles, granola bars, oatmeal packets, microwavable popcorn, and a Keurig machine with K-Cups, sugar, creamer, and tea. In addition, included with your stay is soap, shampoo and conditioner. Just in case you left at home we also include an individually wrapped toothbrush and package of Colgate toothpaste!
- WiFi (strong signal with a WiFi extenders throughout)
Outdoor Amenities:
- Two fire pits, BBQs, Adirondack chairs, picnic tables, and backyard games.
- Firewood and fire starters provided.
Pets: We love pets and try to ensure you and your furry friends enjoy your trip! There is a $25 pet fee per pet. Any damage, unannounced or non-permitted pets will incur a $250 charge. With that in mind, we ask you to clean up as best as possible.
History & Location:
The Stephentown Hotel, built in the 1860s, is a historical gem and the last of four original railroad hotels in the area. Featured in the 2009 film `Taking Woodstock` by Ang Lee. Located minutes from Jiminy Peak Ski Resort, nestled in the serene Berkshire Mountains, right on the NY/MASS border. The hotel underwent a 3 year gut renovation reopening in 2023.
Nearby Attractions:
Enjoy skiing at Jiminy Peak Mountain Resort, horseback riding at Cinch `em Up Stables, Blacksmith Knife Making Classes at Heather`s Heart Forge Blacksmith, local independent bookstore Braveheart Books & Bazaar, and many more adventures and local experiences listed in our guidebook. We created two maps of nearby restaurants, bars, farm stands, breweries, orchards, activities and adventures.
Security cameras are installed at the entrances; none inside apartments.
Provide the full name of every guest at booking.
Reply with `EXPECT NOTHING, APPRECIATE EVERYTHING.` to confirm you’ve read the house rules.
Thank you for choosing the Stephentown Hotel for your stay! We look forward to hosting you.
Welcome to the historic Stephentown Hotel! This unique property offers the entire building with four private apartments, each with its own entrance. Whether you`re planning a family reunion, a group ski trip, or a serene getaway, this space is perfect for up to 28 guests.
Accommodations:
- Total Capacity: 28 guests
- Bedrooms: 10 (4 King beds, 6 Queen beds, 2 pullout sofas, 2 regular couches)
- Bathrooms: 6
- Living Rooms: 5
- Kitchens: 4
- Arcade Rooms: 4 (one in every apartment)
- Outdoor Spaces: 2 private amenity areas with fire pits, BBQs, outdoor games, picnic tables, fire wood, fire starter and more.
Apartment Breakdown:
- Apartment 1 (1st FL): 2 Bedrooms (two Queen beds), 1 Bathroom, Living Room with 2 Sleeper Sofas, Large Eat-in Kitchen, Arcade. Capacity: 6 guests.
- Apartment 2 (1st FL): Studio Layout, 1 King Bed, 1 Queen Pullout Couch, 1 Sleeper Sofa, Eat-in Kitchen, Private Deck, Arcade. Capacity: 4 guests.
Apartment 3 (1st/2nd FL): Triplex with 5 Bedrooms, 3 Bathrooms, 2 Living Rooms, Large Eat-in Kitchen, Arcade, Private Washer/Dryer, Large Deck. Capacity: 12 guests.
Apartment 4 (2nd FL): 2 Bedrooms (King and Queen beds), 1 Bathroom, Living Room with Queen Pullout, Large Eat-in Kitchen, Arcade, Large Deck, Private Washer/Dryer. Capacity: 6 guests.
Amenities:
- Ductless AC units with individual remotes in every bedroom and living room.
- Two washer/dryer units available (in Apartments 3 and 4).
- Keurig machines, Smart TVs, blackout shades, and more in each apartment.
- Culligan water filtration system for fresh-tasting water throughout the building.
- S’mores goodie bags included for stays between May 1st and November 1st.
- fully furnished kitchens with pots, pans, utensils, and basic cooking supplies. Enjoy complimentary water bottles, granola bars, oatmeal packets, microwavable popcorn, and a Keurig machine with K-Cups, sugar, creamer, and tea. In addition, included with your stay is soap, shampoo and conditioner. Just in case you left at home we also include an individually wrapped toothbrush and package of Colgate toothpaste!
- WiFi (strong signal with a WiFi extenders throughout)
Outdoor Amenities:
- Two fire pits, BBQs, Adirondack chairs, picnic tables, and backyard games.
- Firewood and fire starters provided.
Pets: We love pets and try to ensure you and your furry friends enjoy your trip! There is a $25 pet fee per pet. Any damage, unannounced or non-permitted pets will incur a $250 charge. With that in mind, we ask you to clean up as best as possible.
History & Location:
The Stephentown Hotel, built in the 1860s, is a historical gem and the last of four original railroad hotels in the area. Featured in the 2009 film `Taking Woodstock` by Ang Lee. Located minutes from Jiminy Peak Ski Resort, nestled in the serene Berkshire Mountains, right on the NY/MASS border. The hotel underwent a 3 year gut renovation reopening in 2023.
Nearby Attractions:
Enjoy skiing at Jiminy Peak Mountain Resort, horseback riding at Cinch `em Up Stables, Blacksmith Knife Making Classes at Heather`s Heart Forge Blacksmith, local independent bookstore Braveheart Books & Bazaar, and many more adventures and local experiences listed in our guidebook. We created two maps of nearby restaurants, bars, farm stands, breweries, orchards, activities and adventures.
Security cameras are installed at the entrances; none inside apartments.
Provide the full name of every guest at booking.
Reply with `EXPECT NOTHING, APPRECIATE EVERYTHING.` to confirm you’ve read the house rules.
Thank you for choosing the Stephentown Hotel for your stay! We look forward to hosting you.
During your stay at this holiday home, you'll be close to Jiminy Peak Mountain Resort. You'll find features such as laundry facilities. A kitchen and 6 bathrooms are available in the holiday home.
- Air-conditioned home with kitchen, washing machine and 6 bathrooms
- Amenities include laundry facilities
- Just a 5-minute drive from Zema's Nursery and 7 minutes from Jiminy Peak Mountain Resort
The entire Stephentown Hotel! 28 person occupancy offers its guests barbecue grills and laundry facilities. The front desk is open around the clock.
Property amenities
Internet
- Available in the house: WiFi
Parking and transport
- Parking on site
Bedrooms
- 9 bedrooms
- Sofa bed
Bathroom
- 6 bathrooms
Entertainment
- Books
- Games
- TV
Outdoor areas
- Barbecue grill
- Firepit
- Patio
Laundry
- Laundry facilities
- Washing machine
Work spaces
- Desk
Comfort
- Air conditioning
Pets
- Pet friendly
Suitability/Accessibility
- Smoke-free property
Location highlights
- In the mountains
Safety features
- Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
- Smoke detector (host has indicated there is a smoke detector on the property)
- Fire extinguisher
General
- Unit size: 6,566 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Minimum check-in age - 21
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Pets
- Pets are welcome Service animals are exempt from fees.
Children and extra beds
- Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account, which will enable you to manage your booking.
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.
Property is also known as
210510