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Stephentown Center Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Stephentown Center holiday rentals

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,748 reviews)
"This was a fantastic property to end our New England trip!"
United States
Adrianne
The price is NZ$179
includes taxes & fees
16 Nov - 17 Nov
Vacation Village in the Berkshires
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,208 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
United States
Joel
The price is NZ$212
includes taxes & fees
10 Nov - 11 Nov
Berkshire Mountain Lodge
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

3. 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 NZ$439
includes taxes & fees
22 Oct - 23 Oct
Berkshires Apartment at the Stephentown Hotel
A bedroom with a wooden bed, a window with a view of trees, and a red chair.

4. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
10.0 out of 10, Exceptional, (1 review)
"The cabin was just what we needed! A gorgeous fall day, trees only visible from the window. The cabin had a comfortable bed, plenty of blanket and a chair. A rocker was on the porch. From this cabin, you turn right from the door and walk straight to the Bessie Woods trail. The common area had everything we needed, clean, comfortable. If you want to relax, this is pretty special!"
United States
Trena
The price is NZ$328
includes taxes & fees
22 Oct - 23 Oct
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
A snow-covered outdoor area with a fire pit, tables, and chairs.

5. 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 NZ$485
includes taxes & fees
22 Oct - 23 Oct
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A wooden cabin with a porch, a door, and a window.

6. Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (19 reviews)
"Good location for sightseeing around the north east and New England"
United States
Nathan
The price is NZ$301
includes taxes & fees
22 Oct - 23 Oct
Taborton Harvest Boulder Pines Cabin in the woods
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

7. 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 NZ$485
includes taxes & fees
22 Oct - 23 Oct
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Four people seated at a table with food and drinks, wearing winter sports helmets.

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

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (9 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

9. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
The price is NZ$485
includes taxes & fees
22 Oct - 23 Oct
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

10. 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)
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

11. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.0 out of 10, Wonderful, (8 reviews)
"Excellent communication with our host and property exactly as described. Easy check in/check out."
United States
Jillian G.
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
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
8.6 out of 10, Excellent, (7 reviews)
The price is NZ$362
includes taxes & fees
18 Oct - 19 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.

13. 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 NZ$503
includes taxes & fees
18 Oct - 19 Oct
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A spacious kitchen with wooden cabinets, a large island, and a dining area with benches.

14. Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience
Sand Lake
10.0 out of 10, Exceptional, (6 reviews)
"It was a great getaway "
United States
Chandra F.
The price is NZ$301
includes taxes & fees
18 Oct - 19 Oct
Taborton Harvest Timber Trails Unique cabin experience
A spacious living room with a dining area, a kitchen, and a large window.

15. 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 NZ$389
includes taxes & fees
9 Nov - 10 Nov
1800s Carriage house in Berkshires / Hudson Valley
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

16. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (8 reviews)
"A lovely house! Very convenient for a Tanglewood weekend."
United States
Robert B.
The price is NZ$1,003
includes taxes & fees
22 Oct - 23 Oct
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
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
3.0 star property
Stephentown
The price is NZ$986
includes taxes & fees
18 Oct - 19 Oct
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A sign for The Stephentown Hotel with a depiction of a red building and mountains.

18. 2 Bed Berkshire Getaway @ Stephentown Hotel

2 Bed Berkshire Getaway @ Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (7 reviews)
"This place is amazing! It is so clean and updated with lots of amenities! Lots of arcade games in the apartment thatthe whole family enjoyed! It's a quick trip to jimney peak to ski it's just down the road. Great restaurants nearby. Definitely recommend this place."
United States
elizabeth r.
The price is NZ$542
includes taxes & fees
18 Oct - 19 Oct
2 Bed Berkshire Getaway @ Stephentown Hotel
A wooden deck with outdoor furniture, a glass door leading to a view of a grassy area with trees.

19. Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Hancock
8.0 out of 10, Very good, (1 review)
"I chose this place at the very last minute. It was all that I expected and wanted and more: two bedrooms with three beds, a comfortable living space, two full bathrooms, kitchen with all the basic necessities, TV in each bedroom and in the living room, a dining table and chairs, an outside porch with table, a big open space, and grill, easy parking and access, quiet, .and access to two pools. The place was well tended: clean, with towels and extras blankets ready. Howard, the owner, checked on...
United States
Cecilia S.
The price is NZ$565
includes taxes & fees
19 Oct - 20 Oct
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

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

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
Hancock
9.8 out of 10, Exceptional, (6 reviews)
"Great location on mountain and great communication by unit owner."
United States
Marc F.
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"The room and the hotel looked very clean, and the staff were very friendly. Also, the breakfast offered a good variety."
Luisa 1-night trip
Posted 3 hours ago
The Yankee Inn

Find out more about Stephentown Center

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Stephentown Center holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Stephentown Center. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Stephentown Center. Seeing all the best attractions is bound to make you fall in love with Stephentown Center. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Stephentown Center short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Stephentown Center?

Yes, there are holiday rentals close to the most popular sights in Stephentown Center, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Stephentown Center has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Stephentown Center is located near skiing, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday 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 wider area.

What are holiday rentals like in Stephentown Center?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Stephentown Center. Holiday rentals provide amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family trips.