Stephentown Center Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Stephentown Center vacation rentals

Indoor pool

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,829 reviews)
"Great resort, great location very spacious."
United States
Marcos
The price is CA $112
CA $141 total
includes taxes & fees
Nov 8 - Nov 9
Vacation Village in the Berkshires
Exterior

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,256 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is CA $107
CA $151 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Mountain Lodge
A wooden cabin with a porch, a door, and a window.

3. Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (20 reviews)
"Good location for sightseeing around the north east and New England"
United States
Nathan
The price is CA $157
CA $224 total
includes taxes & fees
Nov 6 - Nov 7
Taborton Harvest Boulder Pines Cabin in the woods
A cozy living room with a large window, wooden walls, and a television.

4. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is CA $150
CA $313 total
includes taxes & fees
Nov 8 - Nov 9
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

5. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is CA $131
CA $308 total
includes taxes & fees
Nov 9 - Nov 10
Berkshires Apartment at the Stephentown Hotel
A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

6. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is CA $150
CA $313 total
includes taxes & fees
Nov 8 - Nov 9
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

7. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (19 reviews)
"It's super well located, with a view of the hills from the picture window. Everything is comfortable, everything worked, and host's communication was excellent. Highly recommended."
United States
David
The price is CA $150
CA $313 total
includes taxes & fees
Nov 8 - Nov 9
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A bedroom with a large bed, two bedside tables, a painting, and a clock on the wall.

8. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is CA $150
CA $313 total
includes taxes & fees
Nov 8 - Nov 9
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

9. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Hancock
9.6 out of 10, Exceptional, (33 reviews)
"The suite was a great. Comfortable, clean and decorated very nicely. Bed was very comfortable with nice linens and pillows. "
United States
Eileen O.
The price is CA $150
CA $313 total
includes taxes & fees
Nov 8 - Nov 9
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
A cozy living room with a fireplace, leather sofa, and a television.

10. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
The price is CA $150
CA $313 total
includes taxes & fees
Nov 8 - Nov 9
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A row of multi-story buildings with a uniform architectural style, likely a hotel or resort, set against a backdrop of green hills and trees.

11. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"Great place, everything was so easy!!"
United States
Dana
The price is CA $150
CA $313 total
includes taxes & fees
Nov 8 - Nov 9
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

12. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.8 out of 10, Excellent, (8 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is CA $98
CA $270 total
includes taxes & fees
Nov 6 - Nov 7
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious kitchen with wooden cabinets, a large island, and a dining area with benches.

13. Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience
Sand Lake
10.0 out of 10, Exceptional, (7 reviews)
"It was a great getaway "
United States
Chandra F.
The price is CA $157
CA $224 total
includes taxes & fees
Nov 6 - Nov 7
Taborton Harvest Timber Trails Unique cabin experience
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

14. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is CA $355
CA $821 total
includes taxes & fees
Nov 17 - Nov 18
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Pool

15. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (12 reviews)
"Host was proactive in communication and answer each and every question."
United States
Amit
The price is CA $225
CA $722 total
includes taxes & fees
Nov 6 - Nov 7
Comfortable Berkshires retreat on mtn resort, SISO
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

16. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock
9.6 out of 10, Exceptional, (35 reviews)
"We really enjoyed our stay it was a very nice place for a family."
United States
Shmaya G.
The price is CA $225
CA $443 total
includes taxes & fees
Nov 8 - Nov 9
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

17. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.2 out of 10, Wonderful, (10 reviews)
"Great property and the host was extremely responsive and helpful."
United States
Robbie S.
The price is CA $284
CA $800 total
includes taxes & fees
Nov 12 - Nov 13
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

18. Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Hancock
9.8 out of 10, Exceptional, (21 reviews)
"Great location! "
United States
shannon m.
The price is CA $150
CA $313 total
includes taxes & fees
Nov 8 - Nov 9
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
A spacious living room with a dining area, a kitchen, and a large window.

19. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is CA $119
CA $294 total
includes taxes & fees
Nov 9 - Nov 10
1800s Carriage house in Berkshires / Hudson Valley
A sign for The Stephentown Hotel with a logo featuring a building and mountains.

20. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
The price is CA $177
CA $381 total
includes taxes & fees
Nov 9 - Nov 10
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Stephentown Center Hotel Reviews

A multi-story hotel with a classic facade, large windows, and a prominent entrance.
Hotel On North

Hotel On North

Hotel On North
Pittsfield

10/10 Excellent

This is a great hotel. Large rooms, great amenities and a steak house restaurant that is superb. We like it so much we are staying an extra night.
Canada
alan
Reviewed October 8, 2026
Hotel On North

Find out more about Stephentown Center

Everything you need to know about Stephentown Center vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Stephentown Center vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stephentown Center vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Stephentown Center vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stephentown Center. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stephentown Center vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stephentown Center vacation rentals we have selected for you start as low as CA $97 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Stephentown Center rentals

At Expedia, we put the best Stephentown Center vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Stephentown Center rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stephentown Center vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stephentown Center. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there vacation rentals in Stephentown Center?

Yes, we have vacation rentals close to popular attractions in Stephentown Center, or you can go with a more secluded option if you want a relaxing place to stay.

What's the top vacation rental that Stephentown Center has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: You might want to consider this vacation home rental near Stephentown Center, which is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

What can I see and do in Stephentown Center?

While exploring the area, visit family-friendly sights like Berkshire Museum, or get outside and enjoy nature at Brodie Mountain. Jiminy Peak Mountain Resort and Hancock Shaker Village are a couple of places you'll find in the larger area.

What are vacation rentals like in Stephentown Center?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Stephentown Center. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a small group gathering.