Stephentown Center Holiday Rentals

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Holiday Rentals in Stephentown Center

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2138)
"Great place!"
United States
Nicole
The price is NZ$166
includes taxes & fees
23 Nov - 24 Nov
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very good, (985)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
The price is NZ$285
includes taxes & fees
21 Nov - 22 Nov
Jiminy Peak Mountain Resort

Huttopia Berkshires

1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is NZ$373
includes taxes & fees
14 Dec - 15 Dec
Huttopia Berkshires

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (134)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
United States
michelle
The Ponds at Foxhollow

Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake
10.0 out of 10, Exceptional, (13)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
The price is NZ$326
includes taxes & fees
23 Nov - 24 Nov
Taborton Harvest Boulder Pines Cabin in the woods

The Kemble- Built by a US Secretary of State in Lenox

Lenox
10.0 out of 10, Exceptional, (17)
"Perfect house for our family reunion. Everything was perfect."
United States
Michael C.
The Kemble- Built by a US Secretary of State in Lenox

NEW Cozy Apt Bright + Modern W/D

Hudson Park
8.8 out of 10, Excellent, (26)
"The apartment is very cozy, spacious and discreet. Perfect if your just looking for something that’s not too in the open. "
United States
D’Andre D.
The price is NZ$316
includes taxes & fees
20 Nov - 21 Nov
NEW Cozy Apt Bright + Modern W/D

Charming 3-bedroom Cabin for nature lovers

Stephentown
7.0 out of 10, Good, (2)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
The price is NZ$565
includes taxes & fees
24 Nov - 25 Nov
Charming 3-bedroom Cabin for nature lovers

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (15)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is NZ$1,963
includes taxes & fees
9 Dec - 10 Dec
Hancock Village Inn Near Jiminy Peak

Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Old Chatham
9.6 out of 10, Exceptional, (93)
"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "
United States
Daniel R.
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

Safe Sweet Serene - Empire Plaza

2.0 star property
Albany
8.0 out of 10, Very good, (2)
"The building and apartment are dated but very adequate for a studio apartment. Comfortable bed. The neighborhood is great. "
United States
Larry B.
The price is NZ$317
includes taxes & fees
30 Nov - 1 Dec
Safe Sweet Serene - Empire Plaza

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge
10.0 out of 10, Exceptional, (133)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield
9.8 out of 10, Exceptional, (149)
"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."
United States
Sarah A.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale
9.8 out of 10, Exceptional, (19)
"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"
United States
maria f.
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
The price is NZ$1,294
includes taxes & fees
3 Dec - 4 Dec
Comfortable Berkshires retreat on mtn resort, SISO

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
9.2 out of 10, Wonderful, (32)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
United States
Jacquie S.
Amore Estate - beautiful room with many places to explore and relax in.

The Lakeshore House

Niverville
10.0 out of 10, Exceptional, (1)
"Excellent stay!"
United States
KEITARO A.
The price is NZ$1,399
includes taxes & fees
27 Nov - 28 Nov
The Lakeshore House

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

Pownal
9.4 out of 10, Exceptional, (84)
"This unique hideaway was great for our family. The open layout might not work for everyone, but suited us just fine! We were only here a couple nights but enjoyed the location and using the hot tub! "
United States
Elizabeth R.
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

2 bed room Apartment

South End
10.0 out of 10, Exceptional, (5)
"It was definitely a great get away very quiet and peaceful location "
United States
Jonaeh P.
The price is NZ$315
includes taxes & fees
21 Nov - 22 Nov
2 bed room Apartment

Taborton Harvest Timber Trails Unique cabin experience

Sand Lake
10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
United States
Georgia M.
The price is NZ$324
includes taxes & fees
29 Nov - 30 Nov
Taborton Harvest Timber Trails Unique cabin experience
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

Find out more about Stephentown Center

Everything you need to know about Stephentown Center holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Stephentown Center holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Stephentown Center holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stephentown Center holiday rentals we have selected for you start as low as NZ$166 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 holiday 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 holiday.

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 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.