Airport, Pittsfield, MA (PSF-Pittsfield Municipal)
23 min drive
Rooms & beds
2 bedrooms (sleeps 6)
Bedroom 1
1 Queen Bed
Bedroom 2
1 Queen Bed
1 bathroom
Bathroom 1
Spaces
Kitchen
Garden
About this property
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Welcome to the historic Stephentown Hotel! Beautiful 2 bedroom apartment. We are located minutes away from Jiminy Peak Ski Resort in the world famous Berkshire Mountains! Right on the NY / MASS border in Stephentown. Full sized arcade games, fire pits, BBQ and more!
Every stay includes water bottles, granola bars, Hershey`s mini chocolate bars, popcorn, oatmeal packets, coffee / tea, creamers and a fully stocked kitchen with all cooking utensils and essentials. Parking right in front.
This is for Apartment # 1. 1st floor two bedroom apartment in the Stephentown Hotel, located in the only Stephentown on Earth! The building has operated almost continuously since the 1860s! The Stephentown Hotel is well known locally.
We are minutes away from Jiminy Peak Ski Resort, located in the world famous Berkshire & Taconic Mountains! Many fun activities nearby including Jiminy Peak, Ramblewild Adventure Park, Tanglewood, New Lebanon Speedway, Cherry Plains State Park, Mount Greylock, Cinch Em Horse stables, multiple lakes, hiking trails and more!
Two retro arcade games in the living room (Ms. Pac Man & X-Men). Large eat in kitchen, knotty pine wrapped walls in the living room, (x2) comfy queen beds and (x2) two sofa sleepers in the living room. Smart TV in the living room and both bedrooms!
Ductless ACs for heat and AC throughout the apartment, one in each bedroom and another in the living room. Each AC has its own remote.
Private entrance with parking directly in front of the apartment. We have two outdoor amenity spaces. They feature two fire pits, BBQs, Adirondack chairs, picnic tables, cornhole and misc backyard games. We include firewood and fire starters. The two outdoor spaces are shared between the four apartments. Electric fireplace in the living room.
Every stay includes water bottles, granola bars, Hershey`s mini chocolate bars, popcorn, oatmeal packets, coffee / tea, creamers and a fully stocked kitchen with all cooking utensils and essentials. 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 home features a Culligan whole-house water filtration and reverse osmosis system, providing clean, fresh-tasting drinking water from every faucet.
**All reservations from May 1st to November 1st include a S`mores goodie bag! Sticks, marshmallows, graham crackers and chocolate! **
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. Additionally, we also have a travel boaster high chair.
Two pairs of snowshoes are also available upon request.
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 until 1952. The Hotel is the last remaining of the four original railroad hotels in town. The Stephentown Hotel is a historical gem! Building was featured in `Taking Back Woodstock` film in 2009 directed by Ang Lee.
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. 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.
Infant and kid friendly house (not childproof). Pack n’ play available including fresh sheets! In addition, we also have a travel boaster high chair. Please ensure to request items needed during your reservation.
Books and Games: Additionally the apartment is equipped with Monopoly, Jenga, Connect4, a couple books and kids books including: 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 and USB outlets.
Linens: All towels, sheets and duvet covers are laundered after every stay.
Door Code: A new door code will be issued for your stay. After your stay, the code will be disabled.
Noise - The building is an older building (built in the 1860s). Unfortunately if the other units are occupied, you may hear noise from the other apartments. We do provide white noise machines.
Security Cameras: The building has security cameras around the exterior of the property. 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: The unit is non-smoking. There will be a $250 fee for smoking / smoke damage.
We created two maps for local fun, activities, restaurants, bars and breweries to visit during your stay.
Attractions & Nearby Adventures:
Jiminy Peak Mountain Resort - Hancock, MA Cinch `em Up Stables Horseback Riding - Stephentown, NY Braveheart Books - Stephentown, NY Heather`s Heart Forge Blacksmith Knife Making Classes - Stephentown, NY Ramblewild Adventure Park - Lanesborough, MA Tanglewood - Boston Symphony Orchestra - Lenox, MA Lebanon Valley Speedway - West Lebanon, NY Ready Set Play: Kid`s Indoor Playground - Pittsfield, MA UglyMud Studio - Ghent, NY Corkscrew Rail Trail - (multiple access points) Wyomanock Road, Knapp Road, Stephentown, NY & Tilden Road in New Lebanon. Sand Lake Walking Trail - Averill Park, NY Ashuwillticook Rail Trail - Rail Trail, Cheshire, MA Glass Lake - Averill Park, NY Queechy Lake - Canaan, NY Crystal Lake - Averill Park, NY Grafton Lakes State Park - Grafton, NY Bousquet Mountain - Pittsfield, MA Butternut Ski Area and Tubing - Great Barrington, MA Catamount Mountain - Hillsdale, NY Pineridge Cross Country Ski Area - Petersburg, NY Mount Greylock State Reservation, Adams, MA Cherry Plain State Park - Petersburg, NY October Mountain State Forest and Lake - Lee, MA Berkshire Museum - Pittsfield, MA Berkshire Art Museum - North Adams, MA Massachusetts Museum of Contemporary Art - North Adams, MA Shaker Museum Historic Mount Lebanon Site - New Lebanon, NY Hancock Shaker Village - Pittsfield, MA Norman Rockwell Museum - Stockbridge, MA Grafton Peace Pagoda- Petersburg, NY Red Robin Song Animal Sanctuary - New Lebanon, NY Rustic In Nature Antiques! New Lebanon NY Bridge House Vintage - East Chatham, NY Hand Hollow Conservation Area - East Chatham, NY Images Cinema - Williamstown, MA Albert Family Community Forest - East Nassau, NY
Food / Restaurants / Bars / Farms / Fresh Food
Norte Azul Cantina - Stephentown, NY Gardner`s Coffee Shoppe & Ice Cream - Stephentown, NY Dave’s Market - Stephentown, NY Four Fat Fowl Cheese - Stephentown, NY Blueberry Hill Market Cafe - New Lebanon, NY Smile`s Soft Serve Ice Cream - Nassau, NY Gipfel Coffee Company - Averill Park, NY The Berry Patch - Stephentown, NY Ioka Valley Farm - Hancock, MA Wyomanock Farm - Stephentown, NY Sugar Bush Farms - Stephentown, NY La Perla Restaurant - Averill Park, NY M&M`S Tap and Tavern - New Lebanon, NY Jimmy D`s Pizza Royale - New Lebanon, NY Roaring 20s Brewery & Taphouse - New Lebanon, NY Mario’s - New Lebanon, NY Old Man Jeff`s Barbecue Company - Pittsfield, MA Smokey Diva`s - Pittsfield, MA Hot Dog Ranch - Pittsfield, MA Olde Forge Restaurant - Lanesborough, MA Lakeside Bar & Grill - Lanesborough, MA District Kitchen & Bar - Pittsfield, MA The Beer Diviner - Cherry Plain, NY S&S Farm Brewery - Nassau, NY Chatham Brewing - Chatham, NY Home Range Winery - Canaan, NY Sabba Estate Vineyard - Old Chatham, NY Hilltop Orchards - Richmond, MA Balderdash Cellars - Berkshire Winery - Richmond, MA New Lebanon Farmers Market - New Lebanon, NY Maverick`s - Formerly O`Maddie`s - New Lebanon, NY Woodlife Farm Market - New Lebanon, NY Tacos Diablo - Nassau, NY ZIA’S Pizza & Family Restaurant Nassau, NY Zucchini`s - Pittsfield, MA The Roasted Garlic - Pittsfield, MA Canaan General Store - Canaan, NY Lanesborough Local Country Store - Lanesborough, MA 01237
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 Please be respectful of the building’s other tenants. Should you have any issues or questions, please call or text me right away. We take great pride in making sure you have an enjoyable stay.
All guests are required to provide a copy of their ID prior to arrival. The host assumes no responsibility for any personal bodily injury incurred while using and staying in our unit or in the common areas.
Overstaying without the Host’s Consent Policy: Guest(s) agree that a confirmed booking is merely a license granted by the Host to the Guest to enter and use the Listing for the limited duration of the confirmed booking and in accordance with the Guest’s agreement with the Host. Guest(s) further agree to leave our property no later than 11:00AM/10AM (Apt 3) on the day of check-out. If a Guest(s) stays past the agreed upon check-out time without the Host’s consent, the Guest(s) no longer has permission to stay at our property and the Host is entitled to make the Guest(s) leave. In addition, Guest(s) agree that the Host can charge the Guest(s), an additional night of that day’s base rate without discount and any loss of business or refunds to other guests caused by not checking out on time (this does not entitle you to stay an additional night or give you permission to remain at our property).
Our prices include all fees. No hidden fees.
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Pets allowed: dogs less than 23 kg per pet (limit one pet total)
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Smoking
Smoking is not permitted
Please be respectful of the building’s other tenants. Should you have any issues or questions, please call or text me right away.
Important information
You need to know
Property # 2203148vb
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
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
About the area
Stephentown
Stephentown is home to this apartment. Hancock Shaker Village and Williamstown Theatre Festival are cultural highlights, and some of the area's attractions include Zema's Nursery and Mountain Coaster. Alpine Super Slide and Sand Lake Center for the Arts are also worth visiting.
Jiminy Peak Mountain Resort - 8 min drive - 10.4 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
Blueberry Hill Market Cafe - 9 min drive
JJ's Lodge - 8 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 13 May 2026, prices found for a 1-night stay for 2 adults at 2 Bed Berkshire Apt minutes to Jiminy Peak Ski on 22 May 2026 start from £110, 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.
How much is parking at 2 Bed Berkshire Apt minutes to Jiminy Peak Ski?
On-site parking is available at the property.
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).
Reviews
8.4
Very good
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
We had a lovely stay in Stephentown and enjoyed visiting the surrounding area. So close to Tanglewood and everything the Berkshires has to offer. Comfortable and convenient, everything you might need. Loved the details including toothbrushes and toothpaste! Amazing restaurants and fun shops. Would definitely come back :D
Quiet country setting with great open space for our dog to run. Kitchen was well stocked and the beds were very comfortable. Azul is a local gem of a restaurant along with a couple of others. Dillon was easy to get ahold of and the locals very friendly & helpful.
We will stay there from now on, whenever we head back home to visit friends and family. We look forward to seeing the hotel completely finished and to see what else Dillion has planned for Stephentown! <3
We came in town for a graduation party in Grafton. Loved being close to our friends in Stephentown, Berlin, Petersburg and Grafton. Rooms and common areas are just the right size. The convertible sofa in the living room was better than a pull out sofa! No uncomfortable bar to deal with. Met the couple responsible for the cleaning of the property. They knew the history of the building and the area. Gave us a tour of the other soon to be completed renovated areas. Super nice people! Our stay was fantastic!
The apartment was clean and nicely done. The price imwas very reasonable. The arcade games were a nice touch. The problem was that it was incredibly noisy, particularly in the bedroom we tried to sleep in. This was partly due to the neighbors, who were trudging up and down the stairs until all hours, but also largely due to the lack of soundproofing when this place was renovated. We could hear individual conversations from the neighbors where it felt like they were in the same room as us. There were white noise machines in each room, but they were broken and likely wouldn’t have done much good had they worked given just how noisy it was.
Although the listing states construction completed March 2023, major construction was continuing upon our arrival on Friday, 5/26. Around 5PM we discovered there was no hot water nor heat in the unit. Called host who said both were turned off due to ongoing construction. We were NOT given notice of same, thus we did not have time to shower before attending a rehearsal dinner for a wedding the next day. Owner said construction would stop at 5PM and would also stop for the weekend. NOT TRUE. When we returned at around 8PM construction was ongoing. We contacted the owner who stated they needed to compete a few more items. Unfortunately, construction continued until 2:30 AM. We contacted the owner at 10:45 PM but he did not respond.
Other items:
1. 2 tvs did not work properly due to connection issue and a Roku error message.
2. On our first night, we drove up to the building to find some strange man going in and out of the cellar because construction continued until 2:30 AM Saturday morning.
3. No blinds in the shower window.
It is unfortunate that VRBO does not allow pictures as they would certainly document this fact pattern; however, appropriate photos were sent to both the owner and VRBO. VRBO told me they would look further into the matter and get back to me. They never did. It appears, in my opinion, VRBO is both not reputable nor reliable. Disclosure - Owner refunded fees collected but VRBO has yet to return remaining funds. [This is as of 6/25/23]
We stayed at this property for two months while visiting family over the summer. It is great for a family, and has lots of amenities. It’s centrally located to NY and Mass, and all of the hiking and lakes in the area.
It was exactly what we needed. The fire pit was our favorite part. The kitchen has ample supplies for cooking, and the shower is nicely updated.
This is an old historic property, and the entire apartment has the feel of a farm house. We loved it and highly recommend it to anyone who wants to enjoy the outdoors of the area, and a cool little spot in Stephentown.
One more note, the owner was very friendly and answered our calls when we had questions. This place gets two thumbs up.
Unable to accurately review the cleanliness of the property because I was not comfortable enough with the outside/location/appearance of the property to enter.
Communication with the property manager was fine up until the day of check in - I was told that I would be informed if we could check in early depending on the timing of the cleaning service however I did not hear from the property manager until hours after we were scheduled to check in (we were coming from out of town for a 4PM wedding and our check in time was 4PM)
The check in process initially seemed straightforward as I’ve had experience with temporary rentals before however, when we finally had the opportunity to check in just to sleep at our rental, we were met with confusion and we’re extremely concerned.
Despite being located in a remote town essentially on the border between NY and MA, the house’s location was far from any liveliness that existed in the community — not the issue. Though we had anticipated an older, quaint building based on the photos provided in the listing, we were met with a run down, windowless home with no signs of anyone inhabiting it for quite some time.
Because we were only able to get to the home after the wedding ceremony and reception, it wasn’t until late that we were able to contact the property manager with our obvious concerns. After several phone calls and growing frustration, the manager finally responded to my cell phone number with a question mark to which my partner angrily lashed back at.
After failing to hear from the property manager beyond that, my partner and I drove to the location of the event that we had attended as we felt safer parking there than in front of this run down VRBO. We ended up sleeping in our car and we’re informed later that day that the manager would be reporting us.
We never entered the building for fear of safety. We were confused and disoriented by the outer appearance not only looking completely different than the listing but by the lack of immediate response and assistance from the manager.
I had had high hopes for this stay as it seemed to be too good to be true; my initial interactions with the manager were pleasant. However, I left my stay having slept in my car feeling deceived and patronized.
I did take photos of the home and put them side by side what is being advertised for my open case with this this rental and VRBO’s customer service team.
Haley E.
Stayed 1 night in Oct 2021
Response from VrboOwner on 7 Jul 2023
Haley NEVER checked in. She called me at 3AM the morning of checkout (called approx x10 times) and said vile and nasty comments to me. I saved the screenshot. She cursed me out and called me vulgar comments. I replied to the guest via the App to ensure all communication was kept in the platform. Unfortunately, Haley chose extreme obscenities to scare me into refunding her money. She was intoxicated and confirmed she was at a wedding all night.
I have cameras on the property. She drove up at 2:30AM and never once walked into the property. I have proof that I am happy to share. The guest also confirmed she never checked in. The property has many photos and many reviews on other platforms such as Airbnb. Never once did a guest call and curse me out AND at such a late hour.
Check in hours are during normal business hours / not 3AM. No refund will be applied.
Dillon’s place is very spacious and clean. He was quick to respond when we called. Convenient location. Within 1 mile of great coffee shop and an excellent Mexican restaurant. Perfect place for our two children who are under 5. The beds were comfortable. It could use a few more kitchen items. Overall we would stay here again.
renee w.
Stayed 30 nights in Jul 2021
About the host
Hosted by Dillon Nash
Hi I'm Dillon! New York born and raised! Love traveling the world and exploring other cultures. Happy to give recommendations during your stay!
Why they chose this property
Beautiful apartment in the heart of the Berkshires! Located in the historic former Stephentown Hotel. Private apartment with a private entry. Firepit, BBQ and old fashion popcorn machine. 8 minutes to Jiminy Peak Ski Resort! Great restaurants, breweries, wineries all within driving distance.
What makes this property unique
Historic property, minutes to amazing outdoor activities such as lakes, trails, hiking, skiing / snowboarding, snowshoeing, ATV & snowmobile trails and more!
Languages:
English, Spanish
Premier Host
They consistently provide great experiences for their guests