Search Resorts in Stephentown

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Check availability on Resorts in Stephentown

Compare 26 Resorts in Stephentown with updated reviews, rates, and availability.

"This property is great for skiing, especially with kids. There is a nice pool and little movie theater thats prefect for after a day on the slopes."

"Great time at jiminy! This unit was super clean and super convenient to everything at jiminy including the lodge and lifts! Thank you for the speedy communication! Appreciate it! We’ll be back next year! Thanks!"

"We enjoyed staying at this clean, quiet, and comfy property. Close to so many beautiful spots! Only minutes to both New York and Vermont!"

Outdoor Pool by our cabin. Open from Memorial Day weekend through end of August.

"Kim is a wonderful host, and her cabin is just perfect. This is my second time staying at her place, since I like to travel with my dog whenever possible. Very roomy with a high ceiling, but still nice and toasty. It has everything you could want in a full kitchen, and there’s also a great restaurant and country store/deli just a few steps away. We had a great time at the haunt this Halloween season, which I had never done before. Lots of fun things to do, and gorgeous hikes in the area. I have...

"Great property! Great location. Smooth check-in."

"The property manager was great and very communicative. The hotel is the perfect place to stay if skiing at Jiminy peak. Ski school right outside, pool and arcade room for the children."

Save an average of 15% on thousands of hotels when you're signed in

Other property types in Stephentown

"The pool/clubhouse was a bit chaotic but the overall experience of this location was fantastic. It was lovely."

SAR 733 total

includes taxes & fees

1 Dec - 2 Dec

"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....

SAR 614 total

includes taxes & fees

23 Nov - 24 Nov

Recent reviews of Stephentown hotels

5/5 Excellent

"Didn’t like that there are no trays in shower to hold any soaps or bottles while washing… nothing!!! Tub too high for elderly with slightest arthritis. No curtain on shower bathroom window. Took quite a while to get hot water to wash hands in sink. However, the inn is filled with amazing collectibles. The dinner was delicious. Plenty of seats but gave us a table facing wall (but near window) —why not more in middle of room area with more interesting view! And same table for breakfast and dinner until we requested a different table the 2nd time. Friendly service. Twin beds very comfortable better if Full size. Happy to have 2 chairs in room. Wouldn’t stay again due to bathroom issues. "

A verified traveler stayed at The Red Lion Inn

Posted 2 days ago

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

5/5 Excellent

Very good quality of towels.

"The unit was perfect in size, very good quality of towels. For the cribs, they provided new sheets and blanket that was important for us. "

A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Posted 3 days ago

The Constance, The Whitlock, & The Dewey By The Lenox Collection

5/5 Excellent

"This was a comfortable, clean room in a great little shopping and dining neighborhood. The staff was very friendly and helpful. I look forward to staying here again! "

A verified traveler stayed at The Constance, The Whitlock, & The Dewey By The Lenox Collection

Posted 5 days ago

Explore a world of travel with Expedia

Frequently asked questions

What can I expect from a resort vacation in Stephentown?

You deserve some time off, and a resort is just the place to find all the services and amenities you need for a relaxing trip to Stephentown. One of the comfortable resort hotels in the surrounding area could be just what you’re searching for, whether you want a luxurious suite, blissful spa treatments, or fun activities to try.

What's the best resort for my stay in Stephentown?

Our highest-rated resorts near Stephentown: In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort right by Jiminy Peak Mountain Resort. 5.3 mi (8.5 km) from Stephentown. Has ski-in/ski-out access, a fitness center, and a garden. Cozy Cabin on resort property in Cultural Berkshires. - Ski resort right by Jiminy Peak Mountain Resort. 5.2 mi (8.4 km) from Stephentown. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers. All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx. - Only a 5-minute walk from Jiminy Peak Mountain Resort. 5.4 mi (8.6 km) from Stephentown. Amenities include a sauna.

What can I do in Stephentown?

Zema’s Nursery, Jiminy Peak Mountain Resort, and Pittsfield State Forest are a few interesting places to visit nearby. Additional attractions in the area include Hancock Shaker Village and Mount Greylock State Reservation Visitor Center.

What's the seasonal weather like in Stephentown?

The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Stephentown are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

What's the best way to get to and around Stephentown?

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 10.3 mi (16.6 km) away from the heart of the city. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 24.2 mi (38.9 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.

Search Resorts in Stephentown

Check availability on Resorts in Stephentown

Compare 26 Resorts in Stephentown with updated reviews, rates, and availability.

Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base

In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants

Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out

1 Bedroom - Vacation Village in the Berkshires Resort - Hancock

Cozy Cabin on resort property in Cultural Berkshires.

Hot SKI-in SKI-out Rentals Bentley Brook Resort!

Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury

Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort

Bentley Brook: Ultimate Ski-In Ski-Out -Crazy

Vacation Village In The Berkshires 5 Star Resort - Suite B

Pres Week- Bentley Brook Resort - Your Peak Winter Escape

Bentley Brook: Elevate Your Winter Thrills with Premier Ski-In/Ski-Out Luxury

Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

Embark on Alpine Escapades: Bentley Brook Resort Unveils Ski-In/Ski-Out Bliss

Bentley Brook at Jiminy Peak ^ Studio

Slope-Side Ski-in Ski-Out: Bentley Brook Resort

Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl

Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A

All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!

Other property types in Stephentown

The entire Stephentown Hotel! 28 person occupancy

Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

Recent reviews of Stephentown hotels

Recent reviews of Stephentown hotels

The Red Lion Inn

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Popular Destinations

More Accommodation Types in Stephentown

Frequently asked questions