Stephentown Holiday Rentals

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Holiday Rentals in Stephentown

Private country home minutes from the Berkshires
5.4 out of 10, (11)
"Do not stay here! I am an international traveler, backpacker, and am used to some rough accommodations, but this stay was truly awful. My friend and I booked the space for a weekend, despite reading the previous reviews, thinking it could not be that bad. The house was overwhelmingly musty, there was mold up into the windowsills, the carpeting felt damp to walk on, and least of all the beds were hard and uncomfortable. We left after one night. It felt like a health hazard to be there. Neither...
The price is AU$312
includes taxes & fees
5 Nov - 6 Nov
Private country home minutes from the Berkshires
The entire Stephentown Hotel! 28 person occupancy
The entire Stephentown Hotel! 28 person occupancy
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1738)
"The staff was very nice! And the room was spacious and clean with plenty of amenities. "
The price is AU$297
includes taxes & fees
3 Nov - 4 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (912)
"Very quiet and clean. would definitely go back. "
The price is AU$248
includes taxes & fees
2 Nov - 3 Nov
Jiminy Peak Mountain Resort
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (218)
"The room was beautiful. A lot of thought was put into what you would need during your stay. The location was convenient to a lot of sights, biking and restaurants. I would definitely stay again. "
The price is AU$338
includes taxes & fees
12 Nov - 13 Nov
Berkshire Village Carriage House - Super Private!!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (41)
"We had expectations of a peaceful rustic cabin in the woods, and this rental checked almost all of the boxes! The quaint town of Great Barrington was just close enough for convenience, but the house was rural enough to help us all relax and enjoy the quiet. We loved the dock and the firepit, and the house was well-stocked with firewood, towels, and toiletries. "
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Berkshire Lake access
10.0 out of 10, Exceptional, (47)
"The house was very clean and the yard is large. It's a great place for family vacations."
Berkshire Lake access
Outstanding Estate! Pool, Pond, Gym, Trails! 1,000 off your 2025 stay! Inquire!
9.6 out of 10, Exceptional, (84)
"This large home has many comfortable bedrooms, some very large suites. The kitchen is very well stocked. Our family had a wonderful stay. The pool was great, and a center of our enjoyment. Kids also enjoyed the game room."
Outstanding Estate! Pool, Pond, Gym, Trails! 1,000 off your 2025 stay! Inquire!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (116)
"As with our previous several stays, we thoroughly enjoyed the comfort and location of the house. We had a great time and can’t wait to do it all over again next Summer. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
3 Bedroom Lakefront Home with Hot Tub & Fireplace
10.0 out of 10, Exceptional, (105)
"Everything you ever need to have a beautiful getaway on a beautiful lake!"
3 Bedroom Lakefront Home with Hot Tub & Fireplace
Home away from home
8.4 out of 10, Very good, (13)
"Property was in good shape, though I recommend the owner consider refinishing the tub, the current paint job is not so good. The location is too far from downtown Troy to easily walk but is an easy drive. The building has multiple units and finding the right one was a bit tricky, but the place was clean and well-kept overall and parking was easy, I would stay again."
Home away from home
Amore Estate - beautiful room with many places to explore and relax in.
9.8 out of 10, Exceptional, (16)
"Clean, house has plenty of room. Lovely property. "
Amore Estate - beautiful room with many places to explore and relax in.
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (16)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (22)
"This was the perfect spot for two California couples exploring the Berkshires. The home was warm and inviting, with enough room not to feel crowded. A welcome respite after a day of hiking, museum tours and shopping. All of which were conveniently near by... It was lovely. "
Stockbridge Home, Come Experience The Berkshires!
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
10.0 out of 10, Exceptional, (23)
"My partner and I really enjoyed our relaxing stay at this quaint cottage. It was clean, comfortable, and tucked away in a very quiet area. It was easy to get to restaurants and theaters in Pittsfield / Lenox / Stockbridge. The hot tub was also a great way to spend a cozy fall afternoon!"
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Chic Pittsfield Home With A View!
9.4 out of 10, Exceptional, (6)
"Great view from the property, lovely house and yard. Coiuldn't have been a better stay. "
Chic Pittsfield Home With A View!
The Winthrop Estate - 12K SF 32 Acres
10.0 out of 10, Exceptional, (4)
"Everyone enjoyed the stay"
The Winthrop Estate - 12K SF 32 Acres
The Rizzy Apartment
8.0 out of 10, Very good, (4)
"Great time "
The price is AU$294
includes taxes & fees
5 Nov - 6 Nov
The Rizzy Apartment
Wellspring by AvantStay | Indoor Pool + Views
10.0 out of 10, Exceptional, (8)
"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."
Wellspring by AvantStay | Indoor Pool + Views
Find your Sanctuary at The Rectory at Stockbridge
10.0 out of 10, Exceptional, (6)
"The host, Samantha, was ideal! She was communicative, accomodating, and attentive. The place was perfect, right in the heart of town"
The price is AU$1,648
includes taxes & fees
8 Nov - 9 Nov
Find your Sanctuary at The Rectory at Stockbridge
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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Other types of properties in Stephentown you may be interested in

Hyatt Place Albany/Downtown
3.0 star property
8.8 out of 10, Excellent, (693)
"The parking situation is extremely inconvenient. Please do valet?"
The price is AU$207
includes taxes & fees
1 Dec - 2 Dec
Hyatt Place Albany/Downtown
Comfort Inn Glenmont - Albany South
2.5 star property
7.8 out of 10, Good, (875)
"A wonderful place to stay! "
The price is AU$158
includes taxes & fees
1 Dec - 2 Dec
Comfort Inn Glenmont - Albany South
Hilton Albany
3.5 star property
7.0 out of 10, Good, (1013)
"This hotel is declining. The rooms are starting to show their age. The shuttle service is important, but they need back up drivers. The front desk would not transfer me to a guest I named because I didn’t have their room number. If I had that, I wouldn’t have called the desk! This was very peculiar and never-before experienced anywhere! I’ve stayed there for years and am starting to see negative trends!"
The price is AU$234
includes taxes & fees
1 Dec - 2 Dec
Hilton Albany
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.

Frequently asked questions

Are there holiday rentals in Stephentown?

Yes, there are holiday rentals in Stephentown close to Zema's Nursery, or you can select a more secluded option if you're looking for a relaxing stay. Stephentown is known for its ski areas and restaurants.

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

Private country home minutes from the Berkshires: This highly rated holiday home rental in Stephentown is located in the mountains, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as a selection of books.

How many holiday rentals are there in Stephentown?

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

What’s there to see and do in Stephentown?

While exploring the area, visit family-friendly sights like Zema's Nursery, or get outside and enjoy nature at Mount Greylock State Reservation Visitor Center. In the wider area, you’ll find Jiminy Peak Mountain Resort and Hancock Shaker Village.

What’s a holiday rental in Stephentown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Stephentown. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip.