In the heart of the Berkshire Mountains, historic Stephentown Hotel offers a charming retreat. This beautiful 2-bedroom apartment features a private entrance, fire pits, BBQs and an old-fashioned popcorn machine on site! Every stay includes water bottles, granola bars and oatmeal packets to fuel your adventures nearby Jiminy Peak Ski Resort.
Reviews
8.48.4 out of 10
Very good
Entire apartment
2 bedrooms1 bathroomSleeps 693 sq m
Popular amenities
Parking available
Pet-friendly
Dryer
Fireplace
Barbecue grill
Kitchen
The current price is AU$419
AU$419
includes taxes & fees
26 Oct - 27 Oct
Add dates for prices
About this property
Entire place
You'll have the entire apartment to yourself and will only share it with other guests in your party.
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Welcome to the historic Stephentown Hotel! Private apartment located minutes to Jiminy Peak Mountain in the world famous Berkshire Mountains! Right on the NY / MASS border in beautiful Stephentown. Surrounded by nature and serenity. Beautiful 2 bedroom apartment with a private entrance, completely renovated, new kitchen and bathroom, fire pit, BBQ and old fashion popcorn machine on site!
Every stay includes water bottles, granola bars, oatmeal packets, coffee and tea! Parking in front.
The apartment was renovated in 2023; brand new kitchen and bathroom. Large eat in kitchen with gas stove, dishwasher and Keurig machine. Bathroom features an incredible rain head shower, Bluetooth light / speaker in the shower to listen to your favorite music. (x2) Comfy queen beds, black out curtains and more. Private entrance and parking directly in front of the apartment. There is a fire pit with chairs and a BBQ. There is also an old fashion popcorn machine! There are two queen sofa beds in the living room.
In addition, included with your stay is soap, shampoo and conditioner. Just in case you left at home - we also included an individually wrapped toothbrush and package of Colgate toothpaste!
The mudroom entry includes a Ski rack and Snowboard rack to hang your gear indoors along with an old fashion popcorn machine! There are two pairs of snowshoes included with your stay. We keep umbrellas and snow brushes in the mudroom. **NO SKI or SNOWBOARD BOOTS INSIDE THE APARTMENT PAST THE MUDROOM**
Some history on the property! The building is the former historic Stephentown Hotel, built in the 1860s as a railroad hotel to serve the increased traffic brought by the railroad from 1869 to 1952. The Hotel is the last remaining of four of the original railroad hotels in town. The Stephentown Hotel is a historical gem! Building was featured in "Taking Back Woodstock" film in 2009. The building will soon again become a mainstay of Stephentown. There is on-going construction at the property (details below).
Every stay includes water bottles, granola bars, oatmeal packets, popcorn, coffee and tea. The kitchen is fully stocked with all utensils and cooking equipment!
Pets: Pets must be given permission. We love pets and try to ensure you and your furry friends enjoy your trip! 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. If needed, there may be an additional $50 cleaning fee per stay (requested after the stay if necessary). This would reflect additional cleaning if needed.
** Construction on site - there is work on going in the building. The building is featuring a major face lift. NO work is being done in the unit. All work is in the main part of the building (the main house). All work is performed during "business hours" to not disturb guests. Work only on weekdays. There will be interior work in the main part of the house (not in the unit.) **
TV: The apartment comes equipped with (x3) smart TVs to Cast direct to!
Books and Games: Additionally the apartment is equipped with Monopoly, Jenga, Connect4, a couple books including two kids books: The Hungry Caterpillar & One Fish, Two Fish, Red Fish, Blue Fish.
The apartment is equipped with a blow dryer, Keurig machine for coffee, sweetener, creamer, tea bags, corkscrew / bottle opener, pizza cutter, toaster, cutlery, cutting board, ice trays, dishes, pots, pans, laundry detergent, bluetooth speaker and USB outlets.
Bathroom has a bluetooth speaker in the light! Turn the light switch on and search for HOMEWERKS in the bluetooth settings to connect!
Linens: All towels, sheets and duvet covers are laundered after every stay. There is a laundry room next to the unit.
Door Code: A new door code will be issued for your stay. After your stay, the code will be disabled.
Security Cameras: The building has security cameras at the main entrance and inside the building’s lobby / common areas. There are NO video or recording devices in the unit. IF you see anything suspicious - PLEASE ALERT ME IMMEDIATELY.
Parking - For any boat / trailer / snowmobile, etc. permission must be requested prior.
Smoking: There is no smoking inside the house. Recreational Marijuana - RM is legal for purchase in Massachusetts. RM is not to be smoked in the house.
We created two maps for local fun, activities, restaurants, bars and breweries to visit during your stay.
Attractions & Nearby Adventures:
Jiminy Peak Mountain Resort Cinch 'em Up Stables Horseback Riding Braveheart Books Heather's Heart Forge Blacksmith Knife Making Classes Ramblewild Adventure Park Tanglewood - Boston Symphony Orchestra Lebanon Valley Speedway Ready Set Play: Kid's Indoor Playground UglyMud Studio Corkscrew Rail Trail - (multiple access points) Wyomanock Road, Knapp Road, Stephentown, NY & Tilden Road in New Lebanon. Sand Lake Walking Trail Ashuwillticook Rail Trail Glass Lake Queechy Lake Crystal Lake Grafton Lakes State Park Bousquet Mountain Butternut Ski Area and Tubing Catamount Mountain Pineridge Cross Country Ski Area Mount Greylock State Reservation Cherry Plain State Park October Mountain State Forest and Lake Berkshire Museum Berkshire Art Museum Massachusetts Museum of Contemporary Art Shaker Museum Historic Mount Lebanon Site Hancock Shaker Village Norman Rockwell Museum Grafton Peace Pagoda Red Robin Song Animal Sanctuary Rustic In Nature Antiques! Bridge House Vintage Hand Hollow Conservation Area Images Cinema Albert Family Community Forest
Food / Restaurants / Bars / Farms / Fresh Food
Norte Azul Cantina Gardner's Coffee Shoppe & Ice Cream Dave’s Market Four Fat Fowl Cheese Blueberry Hill Market Cafe Smile's Soft Serve Ice Cream Gipfel Coffee Company The Berry Patch Ioka Valley Farm Wyomanock Farm Sugar Bush Farms La Perla Restaurant M&M'S Tap and Tavern Jimmy D's Pizza Royale Roaring 20s Brewery & Taphouse Mario’s The Beer Diviner S&S Farm Brewery Chatham Brewing Home Range Winery Sabba Estate Vineyard Hilltop Orchards Balderdash Cellars New Lebanon Farmers Market Maverick's - Formerly O'Maddie's Woodlife Farm Market Tacos Diablo ZIA’S Pizza & Family Restaurant Zucchini's The Roasted Garlic Canaan General Store Lanesborough Local Country Store
Please check out our guidebook for some amazing adventures, activities, restaurants, bars, farms and more! At booking, provide the full name (as listed on Government issued ID) for every person that will access the property during your reservation.
** Construction on site - there is work on going in the building. The building is featuring a major face lift. NO work is being done in the unit. All work is in the main part of the building (the main house). All work is performed during "business hours" to not disturb guests. Work only on weekdays. There will be interior work in the main part of the house (not in the unit.) **
The building is an older building (built in the 1860s). Unfortunately if the other units are occupied, you will hear noise from the other apartments. We do provide (x3) white noise machines.
Property amenities
Internet
Available in the apartment: WiFi
Parking and transport
Parking on site
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Hob
Microwave
Oven
Refrigerator
Toaster
Dining
Dining table
Bedrooms
2 bedrooms
Bedsheets provided
Sofa bed
Bathroom
1 bathroom
Hair dryer
Living spaces
Dining table
Fireplace
Entertainment
Games
Stereo
TV
Outdoor areas
Barbecue grill
Firepit
Garden
Laundry
Dryer
Laundry facilities
Work spaces
Desk
Comfort
Air conditioning
Heating
Pets
Pet friendly
Welcoming dogs only
Up to 23 kg per pet
Suitability/Accessibility
Smoke-free property
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)
You will receive an email from the host with check-in and check-out instructions
Pets
Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total (up to 23 kg per pet)
Children and extra beds
Children are welcome
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
Property is also known as
House
Vrbo Property
210505
2 Bed Berkshire Getaway Stephentown NY Stephentown
2 Bed Berkshire Getaway Stephentown NY Private vacation home
About the area
Stephentown, NY
What's nearby
Zema's Nursery - 6 min drive - 6.4 km
Jiminy Peak Mountain Resort - 17 min drive - 10.8 km
Mount Greylock State Reservation Visitor Center - 23 min drive - 22.8 km
Williams College - 33 min drive - 34.8 km
Tanglewood Music Center - 37 min drive - 39.9 km
Getting around
Pittsfield Intermodal Transportation Center - 24 min drive
Pittsfield, MA (PSF-Pittsfield Municipal) - 21 min drive
Restaurants
Stewart's Shops - 9 min drive
Cumberland Farms - 8 min walk
Norte Azul Cantina - 6 min walk
Blueberry Hill Market Cafe - 9 min drive
M&M'S Tap and Tavern - 9 min drive
Frequently asked questions
Is 2 Bed Berkshire Apt minutes to Jiminy Peak Ski pet-friendly?
Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.
How much does it cost to stay at 2 Bed Berkshire Apt minutes to Jiminy Peak Ski?
As of 20 Oct 2025, prices found for a 1-night stay for 2 adults at 2 Bed Berkshire Apt minutes to Jiminy Peak Ski on 26 Oct 2025 start from AU$419.02, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
What time is check-in at 2 Bed Berkshire Apt minutes to Jiminy Peak Ski?
Check-in begins at 4:00 PM.
What time is check-out at 2 Bed Berkshire Apt minutes to Jiminy Peak Ski?
Checkout is at 11:00 AM.
Where is 2 Bed Berkshire Apt minutes to Jiminy Peak Ski located?
Situated in Stephentown, this apartment building is 2.8 mi (4.6 km) from Taconic Ridge State Forest and 3.1 mi (5 km) from Zema's Nursery. Jiminy Peak Mountain Resort and Mountain Coaster are also within 6 miles (10 km).
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