2 Bed Berkshire Getaway @ Stephentown Hotel

Welcome to the Stephentown Hotel in the heart of the Berkshire & Taconic Mountains. Completely gut remodeled two bedroom apartment, the building reopened in 2023.

Two bedroom apartment, brand new everything! Located on the 2nd FL of the historic Stephentown Hotel. Large bedrooms, custom kitchen, soaking bathtub, bright and spacious with plenty of windows, ductless ACs, arcade with x3 arcade games plus a Washer Dryer in unit. Located minutes from Jiminy Peak!

The space
The building went through a 2.5 year complete gut remodel. We are located minutes away from Jiminy Peak Ski Resort in the world famous Berkshire & Taconic Mountains! Right on the NY / MASS border in beautiful Stephentown. Surrounded by nature and serenity. Many fun activities nearby including Tanglewood, New Lebanon Speedway, Cherry Plains State Park, Mount Greylock, Cinch Em Horse stables, multiple lakes, hiking trails and more!

Beautiful 2 bedroom apartment, King Bed in the primary along with a Queen bed in the second bedroom, queen pull out sleeper sofa in the living room, custom kitchen with granite countertop, dishwasher, gas stove, soaking bathtub, arcade with (x3) games (Ms Pac Man, Big Buck Hunter & Golden Tee Golf), ductless ACs in the bedrooms and living room, in-unit washer / dryer, Smart TVs in each bedroom & living room and plenty of light with windows on 3 sides!

Every stay includes water bottles, granola bars, popcorn, oatmeal packets, coffee / tea, creamers and a fully stocked kitchen with all essential utensils. 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!

We offer a travel pack n play (Graco® Pack 'n Play® On the Go™ Playard). It features a removable bassinet. If you need the pack n play, please send a request. We keep two on hand and brought out by request only. We have a set of sheets that are cleaned for your use.

Culligan water treatment system for fresh water throughout the house.

Some history on the property! The building is the 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.

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.

TV: The apartment comes equipped with (x3) smart TVs to Cast direct to!

Arcade, Books and Games: We have an arcade room with three full sized arcade games along with an old fashion popcorn machine. 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.) **

Stephentown Airbnb. Stephentown VRBO. Jiminy Peak Airbnb. Jiminy Peak VRBO. Ski Jiminy Peak.

If you have read it this far, THANK YOU for being a SUPER GUEST! Please reply back with my favorite quote: “EXPECT NOTHING, APPRECIATE EVERYTHING.” so that I know that the house rules have been reviewed

Guest access
Private apartment with private entry.

Other things to note
We offer a travel pack n play (Graco® Pack 'n Play® On the Go™ Playard). It features a removable bassinet. If you need the pack n play, please send a request. We keep two on hand and brought out by request only. We have a set of sheets that are cleaned for your use.

** 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.) **