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
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, (1746)
"The pool/clubhouse was a bit chaotic but the overall experience of this location was fantastic. It was lovely."
The price is HK$1,313
HK$1,519 total
includes taxes & fees
25 Nov - 26 Nov
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$1,160
HK$1,272 total
includes taxes & fees
25 Nov - 26 Nov
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, (225)
"One of the best properties i've ever stayed at "
The price is HK$1,113
HK$1,721 total
includes taxes & fees
25 Nov - 26 Nov
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, (47)
"The house was very clean and the yard is large. It's a great place for family vacations."
Berkshire Lake access
Beautiful One-of-a Kind Private Estate! Pool, Gym, Arcade, Trails, Pond, Library
Fridge, microwave, oven, stovetop
Beautiful One-of-a Kind Private Estate! Pool, Gym, Arcade, Trails, Pond, Library
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."
Beautiful One-of-a Kind Private Estate! Pool, Gym, Arcade, Trails, Pond, Library
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, (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
View from property
3 Bedroom Lakefront Home with Hot Tub & Fireplace
10.0 out of 10, Exceptional, (107)
"Very glad to have found Nana’s Place. It’s been perfect for us every time. Thank you!"
3 Bedroom Lakefront Home with Hot Tub & Fireplace
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
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!
Chic Pittsfield Home With A View!
Property grounds
Chic Pittsfield Home With A View!
8.8 out of 10, Excellent, (8)
"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
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
The Rizzy Apartment
Smart TV
The Rizzy Apartment
8.0 out of 10, Very good, (4)
"Great time "
The price is HK$739
HK$1,110 total
includes taxes & fees
23 Nov - 24 Nov
The Rizzy Apartment
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.
9.8 out of 10, Exceptional, (17)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Terrace/patio
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
9.4 out of 10, Exceptional, (59)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Wellspring by AvantStay | Indoor Pool + Views
Exterior
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
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$895
HK$1,362 total
includes taxes & fees
5 Dec - 6 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
8.8 out of 10, Excellent, (717)
"Parking was convenient and easy to get to highway from location. "
The price is HK$860
HK$980 total
includes taxes & fees
7 Dec - 8 Dec
Hyatt Place Albany/Downtown
Comfort Inn Glenmont - Albany South
Lobby
Comfort Inn Glenmont - Albany South
2.5 star property
7.8 out of 10, Good, (891)
"Nice place to stay. "
The price is HK$710
HK$809 total
includes taxes & fees
8 Dec - 9 Dec
Comfort Inn Glenmont - Albany South
Hotel Downstreet
Hypo-allergenic bedding, laptop workspace, blackout curtains
Hotel Downstreet
3.0 star property
8.6 out of 10, Excellent, (1043)
"Great location, wonderful staff, fun pool and cool art. Would definitely stay again! "
The price is HK$904
HK$1,009 total
includes taxes & fees
5 Dec - 6 Dec
Hotel Downstreet
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.
Beautiful view of the beach with palm trees

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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 6 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.