Stephentown Vacation Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

This weekend
Next weekend

Vacation Rentals in Stephentown

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1759)
"Great place "
The price is ¥23,119
¥26,903 total
includes taxes & fees
Feb 3 - Feb 4
Vacation Village in the Berkshires

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is ¥35,635
¥39,804 total
includes taxes & fees
Feb 14 - Feb 15
The Ponds at Foxhollow by Capital Vacations

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (924)
"Staff was exceptionally helpful and friendly."
The price is ¥29,131
¥31,956 total
includes taxes & fees
Feb 5 - Feb 6
Jiminy Peak Mountain Resort

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (237)
"Overall, our stay was great! My girlfriend and I made a quick decision to head up to the slopes to start the new year and found this perfect spot! Great area, 15 mins to multiple ski resorts, cleanly, easy access, had everything we needed. Will be back for sure!"
The price is ¥23,120
¥35,295 total
includes taxes & fees
Feb 13 - Feb 14
Berkshire Village Carriage House - Super Private!!

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

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

9.4 out of 10, Exceptional, (21)
"Fantastic, large house with tons of places to explore in the house and on the property. We came for a long weekend with 3 families and both the adults and kids felt quickly at home and really enjoyed our stay. We cannot wait to some back!"
Amore Estate - beautiful room with many places to explore and relax in.

Spacious Luxury Berkshire's Estate on 21 acres

Spacious Luxury Berkshire's Estate on 21 acres

Private Estate w/pool, gym, pond, trails, arcade! Chef dinner w/ week long stay!

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!"
Private Estate w/pool, gym, pond, trails, arcade! Chef dinner w/ week long stay!

Chic Madison Parkview

9.8 out of 10, Exceptional, (9)
"Easy access both to parking and to the unit. Comfortable with all of the necessities which made it perfect for our two-night stay. Washington Park is directly across the street and good food options within walking distance."
The price is ¥15,259
¥26,665 total
includes taxes & fees
Feb 1 - Feb 2
Chic Madison Parkview

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

10.0 out of 10, Exceptional, (5)
"Condo was conveniently located at the base of the mountain. Had everything you would need for a quick weekend getaway. Owner was available for any questions."
The price is ¥24,362
¥45,558 total
includes taxes & fees
Feb 3 - Feb 4
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

8.8 out of 10, Excellent, (28)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is ¥17,845
¥44,503 total
includes taxes & fees
Feb 3 - Feb 4
Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (9)
"Annual mother/son ski and food fest!Lots of fun with family and friends. Plenty of space for everyone.. Kitchen wascwell"
The price is ¥92,170
¥161,693 total
includes taxes & fees
Feb 4 - Feb 5
Hancock Village Inn at Jiminy Peak

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

Cabin in the woods

10.0 out of 10, Exceptional, (9)
"This place was awesome... I was 15 minutes away working late... and I was too tired to drive home... I actually scheduled the wrong night and realized it after I got confirmation. But I messaged the renters and they just happened to have a cabin vacancy... they gave me the directions.. the key code and we worked everything out afterwards. The set-up is genius... the common area building has all the plumbing in it. Bathroom and showers with an open very well built living room with a kitchen. My...
The price is ¥18,496
¥26,141 total
includes taxes & fees
Feb 13 - Feb 14
Cabin in the woods

Private Access To Laurel Lake, Enjoy Lake Life

10.0 out of 10, Exceptional, (14)
"The property was better than advertised. Everything anyone could need was provided and we could not have hoped for a better experience. Very large home and could easily accomodate 8 people or more. The Berkshires are magical and this home was great for out time there."
Private Access To Laurel Lake, Enjoy Lake Life

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (65)
"Beautiful home perfect for our multi-generational family. We loved the separate spaces and easy walk to the town center. We can’t wait to come back!"
Enjoy comfortable elegance in this secluded grand home located in town

Chic Pittsfield Home With A View!

8.6 out of 10, Excellent, (10)
"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!

Comfortable Berkshires retreat on mtn resort, SISO

The price is ¥49,630
¥102,497 total
includes taxes & fees
Feb 5 - Feb 6
Comfortable Berkshires retreat on mtn resort, SISO

Wellspring by AvantStay | Indoor Pool + Views

10.0 out of 10, Exceptional, (10)
"We all enjoyed our stay. The house and indoor pool were wonderful. There are plenty of comfortable places to sit and enjoy the gorgeous views. We loved the location which is both close to Lenox restaurants, as well as, the southern Berkshires for food markets and activities for kids. The property manager was attentive, and the owner was very responsive. We loved our week at this family friendly property and highly recommend it. "
Wellspring by AvantStay | Indoor Pool + Views

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

10.0 out of 10, Exceptional, (118)
"Property as described. Great location to towns. Larger interior space than anticipated. Great Kitchen for a group of 5 to cook, chat and enjoy! Overall a warm and spacious home for old college friends to reunite. "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
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.
Don't see what you're looking for?
See all available properties in Stephentown
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Stephentown you may be interested in

Hyatt Place Albany/Downtown

3.0 star property
9.0 out of 10, Wonderful, (807)
"Friendly check-in. Clean room"
The price is ¥20,842
¥23,759 total
includes taxes & fees
Feb 6 - Feb 7
Hyatt Place Albany/Downtown

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.6 out of 10, Excellent, (1003)
"Easy to get to, nice location "
The price is ¥18,015
¥20,124 total
includes taxes & fees
Feb 16 - Feb 17
Hotel Downstreet, Ascend Hotel Collection

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1759)
"Great place "
The price is ¥23,119
¥26,903 total
includes taxes & fees
Feb 3 - Feb 4
Vacation Village in the Berkshires
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 vacation rentals in Stephentown?

Yes, we have vacation rentals in Stephentown close to Zema's Nursery, or you can go with a secluded option if you want a relaxing stay. Stephentown is known for its ski areas and restaurants.

What's the top vacation rental that Stephentown has to offer?

Berkshire Village Carriage House - Super Private!!: This vacation home rental near Stephentown is located in the mountains and has a garden, a barbecue grill, 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 the books in this rental home to help you unwind.

How many vacation rentals are there in Stephentown?

Choose from 5 Expedia vacation rentals in Stephentown for a memorable vacation.

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 larger area, you’ll find Jiminy Peak Mountain Resort and Hancock Shaker Village.

What’s a vacation rental in Stephentown like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Stephentown. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.