Stephentown Vacation Rentals from SAR 262: Search Short-Term Rentals

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Our top choices for Stephentown vacation rentals

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

1. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Stephentown

SAR 2,205 total

includes taxes & fees

15 Nov - 16 Nov

A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

2. Berkshires Apartment at the Stephentown Hotel

Stephentown

Nicole O.

3. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Stephentown

Robbie S.

SAR 2,150 total

includes taxes & fees

15 Nov - 16 Nov

A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.

4. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Stephentown

Christine P.

SAR 898 total

includes taxes & fees

15 Nov - 16 Nov

5. Vacation Village in the Berkshires

Williamstown

Carol

SAR 378 total

includes taxes & fees

15 Nov - 16 Nov

A large building with a prominent tower, surrounded by trees and a winding road.

6. Berkshire Mountain Lodge

Pittsfield

Susan J

SAR 406 total

includes taxes & fees

6 Dec - 7 Dec

A spacious living area with a stone fireplace, comfortable seating, and a view of the kitchen.

7. UNIQUE - 1BR Country Condo @ Jiminy Peak

Hancock

Nancy P.

A hotel room with a bed, a desk, a television, a window with curtains, and artwork on the walls.

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

Hancock

David

A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

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

Hancock

patricia f.

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.

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

Hancock

Dana

A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

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

Hancock

Eileen O.

A cozy living room with a large window, wooden walls, and a television.

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

Hancock

Maura D.

13. Comfortable Berkshires retreat on mtn resort, SISO

Hancock

Amit

SAR 2,598 total

includes taxes & fees

15 Dec - 16 Dec

A rustic wooden interior with shelves stocked with various products, a 'Tree-Free' sign, and a section with bottled beverages.

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

Hancock

Neil J.

A rustic wooden interior with various stalls selling items like books, snacks, and wine.

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

Hancock

Ann

Four people seated at a table with food and drinks, wearing winter sports helmets.

16. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Hancock

Wendy D.

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

Hancock

shannon m.

A cozy living room with a fireplace, leather sofa, and a television.

18. Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby

Hancock

Marc F.

A spacious living area with a high ceiling, a kitchen in the background, and a large abstract painting on the wall.

19. Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

Hancock

Chad J.

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Find vacation rentals that suit your style

Top Stephentown Hotel Reviews

Vacation Village in the Berkshires

Williamstown

10/10 Excellent

Anonymous traveler

A building entrance with a large planter with purple flowers and a small tree.

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

Berkshire Mountain Lodge

Pittsfield

10/10 Excellent

Elliott

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

10/10 Excellent

Gregory

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Michelle

Two Adirondack chairs facing a river with a forested hill in the background.

The Yankee Inn

Lenox

10/10 Excellent

We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!

Colleen

A wooden cabin with a porch and steps leading to a door, surrounded by snow.

Jiminy Peak Mountain Resort

Hancock

10/10 Excellent

Lloyd A.

A wooden cabin with a fire pit in the snow, large windows, and a covered porch area.

Huttopia Berkshires

Williamstown

10/10 Excellent

Dandara

A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

Hilton Garden Inn Lenox Pittsfield

Pittsfield

10/10 Excellent

A small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.

Williamstown Motel

Williamstown

10/10 Excellent

Grantley

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

Berkshires Untold

Lenox

10/10 Excellent

High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free. There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...

Jill

A garden with a swing set, a blue chair, and a flower bed.

Maple Terrace Motel

Williamstown

10/10 Excellent

Eric

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

Willows Motel Williamstown

Williamstown

10/10 Excellent

Sandra

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

Courtyard by Marriott Lenox Berkshires

Lenox

10/10 Excellent

Alyssa

A kitchen with a countertop, a refrigerator, and a window.

The Villager Motel

Williamstown

10/10 Excellent

Anonymous traveler

Frequently Asked Questions

Are there vacation rentals in Stephentown?

Yes, we have vacation rentals in Stephentown close to Zema's Nursery, or you can go with a secluded option if you want a relaxing stay. Stephentown is known for its ski areas and restaurants.

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

Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game Room: This Stephentown vacation home rental is located in a rural location and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 13 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a pool table and a hot tub.

How many vacation rentals are there in Stephentown?

Choose from 7 Expedia vacation rentals in Stephentown for a memorable vacation.

What’s there to see and do in Stephentown?

Family-friendly attractions include Zema's Nursery, whereas Taconic Ridge State Forest is a spot to enjoy the outdoors. In the larger area, you’ll find Jiminy Peak Mountain Resort and Hancock Shaker Village.

What’s a vacation rental in Stephentown like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Stephentown. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.

Stephentown Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Stephentown vacation rentals

1. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

2. Berkshires Apartment at the Stephentown Hotel

3. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

4. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

5. Vacation Village in the Berkshires

6. Berkshire Mountain Lodge

7. UNIQUE - 1BR Country Condo @ Jiminy Peak

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

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

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

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

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

13. Comfortable Berkshires retreat on mtn resort, SISO

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

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

16. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

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

18. Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby

19. Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

Find vacation rentals that suit your style

Top Stephentown Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Stephentown?

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

How many vacation rentals are there in Stephentown?

What’s there to see and do in Stephentown?

What’s a vacation rental in Stephentown like?