Stephentown Holiday Rentals

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Holiday Rentals in Stephentown

The entire Stephentown Hotel! 28 person occupancy
Private kitchen

The entire Stephentown Hotel! 28 person occupancy

10.0 out of 10, Exceptional, (1)
"We got 7 families to all stay on the property. Lots of fun. Clean and comfortable sleeping accommodations."
The entire Stephentown Hotel! 28 person occupancy
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is HK$1,456
HK$1,675 total
includes taxes & fees
5 Jan - 6 Jan 2025
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is HK$1,468
HK$1,610 total
includes taxes & fees
6 Jan - 7 Jan 2025
Jiminy Peak Mountain Resort
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (232)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is HK$1,134
HK$1,735 total
includes taxes & fees
30 Dec - 31 Dec
Berkshire Village Carriage House - Super Private!!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books

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
Lake

Berkshire Lake access

10.0 out of 10, Exceptional, (49)
"The house worked was exceptionally clean and worked great for us. The landowner was exceptionally helpful in providing suggestions. We loved visiting the Norman Rockwell Museum and walking around Lenox. Thanks for everything!"
Berkshire Lake access
Beautiful 5-Star Private Estate! Inquire about our Early Booking Reduced Rates!
Fridge, microwave, oven, stovetop

Beautiful 5-Star Private Estate! Inquire about our Early Booking Reduced Rates!

9.6 out of 10, Exceptional, (85)
"We had fun! Game room great! Spacious and comfortable. Never got to enjoy outdoors, so maybe another trip in the future!"
Beautiful 5-Star Private Estate! Inquire about our Early Booking Reduced Rates!
3 Bedroom Lakefront Home with Hot Tub & Fireplace
View from property

3 Bedroom Lakefront Home with Hot Tub & Fireplace

10.0 out of 10, Exceptional, (108)
"Wonderful early Christmas celebration with my adult children! It was beautifully decorated for Christmas including a Christmas tree!"
3 Bedroom Lakefront Home with Hot Tub & Fireplace
Amore Estate - beautiful room with many places to explore and relax in.
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (18)
"There was plenty of room for four families. Beds were comfy. If you plan on cooking you might want to bring your own knives and pans. Teflon pans were scraped . Only metal utensil available to flip pancakes. "
Amore Estate - beautiful room with many places to explore and relax in.
Chic Pittsfield Home With A View!
Property grounds

Chic Pittsfield Home With A View!

9.0 out of 10, Wonderful, (9)
"This property was just as shown in the listing and met our needs very well. It was well appointed and had many inviting areas to gather and relax in. The kitchen was well equipped and easy to use. Some very nice touches with closets and bathroom storage areas that made staying there user friendly. "
Chic Pittsfield Home With A View!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining

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

10.0 out of 10, Exceptional, (117)
"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
The Kemble- Built by a US Secretary of State in Lenox
Exterior detail

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!
Fridge, microwave, oven, stovetop

Stockbridge Home, Come Experience The Berkshires!

10.0 out of 10, Exceptional, (24)
"We enjoyed everything about this lovely house in the Berkshires--the latest appliances, thoughtful details (throws on all the beds and sofas), a great backyard. Would highly recommend! "
Stockbridge Home, Come Experience The Berkshires!
Home away from home
Fridge, microwave, oven, stovetop

Home away from home

8.2 out of 10, Very good, (14)
"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
Wellspring by AvantStay | Indoor Pool + Views
Exterior

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (9)
"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
Mountainside Condo Ski In Ski Out
Pool

Mountainside Condo Ski In Ski Out

9.0 out of 10, Wonderful, (21)
"Stay at Jiminey for the 13 nights. Condo was clean and had anything you could ever need! "
The price is HK$1,157
HK$1,457 total
includes taxes & fees
20 Jan - 21 Jan 2025
Mountainside Condo Ski In Ski Out
The Winthrop Estate - 12K SF 32 Acres
Exterior

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
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

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
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Interior

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (37)
"The home was convenient to hiking, shopping and dining. It is on a busy street and can be a bit tricky getting in and out of driveway. Inside the home was warm and welcoming. The kitchen had all cooking pans and tools we needed to make meals. There is a great grocery store right down the road. The beds were comfortable and the bathrooms were clean. The hostess was very helpful and attentive when we had a question about the heat. Be aware the staircase to upstairs bedrooms and 2nd bathroom are...
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
2 bedroom town house with game room
Miscellaneous

2 bedroom town house with game room

6.4 out of 10, (13)
"Comfortable and presentable. Location is great for going downtown or shopping in general. Restaurants are very close by. Property manager was easy to communicate with."
The price is HK$699
HK$1,165 total
includes taxes & fees
30 Dec - 31 Dec
2 bedroom town house with game room
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
Reception

Hyatt Place Albany/Downtown

3.0 star property
9.0 out of 10, Wonderful, (761)
"Everything was good. I enjoyed my stay"
The price is HK$979
HK$1,116 total
includes taxes & fees
1 Jan - 2 Jan 2025
Hyatt Place Albany/Downtown
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Lobby

Hampton Inn & Suites Albany-Downtown

2.5 star property
8.6 out of 10, Excellent, (1003)
"Good "
The price is HK$957
HK$1,091 total
includes taxes & fees
19 Jan - 20 Jan 2025
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Comfort Inn Glenmont - Albany South
Lobby

Comfort Inn Glenmont - Albany South

2.5 star property
7.8 out of 10, Good, (913)
"Nice clean hotel but hot tub was working and restaurant was not open. Great hotel for the price. "
The price is HK$748
HK$853 total
includes taxes & fees
2 Jan - 3 Jan 2025
Comfort Inn Glenmont - Albany South
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?

Berkshire Village Carriage House - Super Private!!: This holiday home rental outside of Stephentown is located in the mountains, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of books in this rental home to help you unwind.

How many holiday rentals are there in Stephentown?

Choose from 5 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 Pittsfield State Forest. 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.