Stephentown Holiday Rentals

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Check prices for these dates

Tonight
13 Nov - 14 Nov
Tomorrow
14 Nov - 15 Nov
This weekend
14 Nov - 16 Nov
Next weekend
21 Nov - 23 Nov

Holiday Rentals in Stephentown

Interior
Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers

Stephentown
7.0 out of 10, Good, (2)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
United States
John O.
The price is HK$1,204
HK$2,484 total
includes taxes & fees
17 Nov - 18 Nov
Charming 3-bedroom Cabin for nature lovers
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2133)
"We came here because it was off season, great price, and it had an indoor pool. "
United States
Monica
The price is HK$741
HK$912 total
includes taxes & fees
14 Nov - 15 Nov
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very good, (984)
"We didn't spend much time there, but it was nice, comfortable, clean and quiet. It was close to the things we had planned to do."
United States
Philip
The price is HK$1,123
HK$1,255 total
includes taxes & fees
14 Nov - 15 Nov
Jiminy Peak Mountain Resort
Exterior
Huttopia Berkshires

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 HK$1,469
HK$1,641 total
includes taxes & fees
14 Dec - 15 Dec
Huttopia Berkshires
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (133)
"Perfect location "
United States
krystle
The price is HK$1,079
HK$1,206 total
includes taxes & fees
5 Dec - 6 Dec
The Ponds at Foxhollow
Exterior detail
Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake
10.0 out of 10, Exceptional, (13)
"We LOVED our stay! Cabins were spotless and the main building was just great! Waking up to a picture window behind us with all the fall colors in their glory was such a highlight. "
United States
Barb W.
The price is HK$971
HK$1,432 total
includes taxes & fees
14 Nov - 15 Nov
Taborton Harvest Boulder Pines Cabin in the woods
Games room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.0 out of 10, Wonderful, (4)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,574
HK$2,313 total
includes taxes & fees
14 Nov - 15 Nov
Pet Friendly Riverfront Home in Great Barrington
1 bedroom, iron/ironing board, WiFi, bed sheets
NEW Cozy Apt Bright + Modern W/D

NEW Cozy Apt Bright + Modern W/D

Hudson Park
8.8 out of 10, Excellent, (26)
"Quiet, safe neighborhood walked three block to the supermarket was able to cook the bed was very comfortable great shower pressure and the place was cleanl, I recommend will be back."
United States
Desiree S.
The price is HK$587
HK$1,390 total
includes taxes & fees
19 Nov - 20 Nov
NEW Cozy Apt Bright + Modern W/D
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox

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

Lenox
10.0 out of 10, Exceptional, (17)
"We booked this house as the venue for our wedding, and it was absolutely perfect! Every room was gorgeous, with elegant décor and plenty of space for our guests. Even the bathrooms were stunning, making every part of the home feel special. The kitchen had everything we needed to host our 50-person wedding, from all the utensils to the appliances, making meal prep and serving a breeze. The communication with the hosts was amazing—Daniel was quick to respond, incredibly helpful, and made sure...
United Kingdom
Carrie S.
The Kemble- Built by a US Secretary of State in Lenox
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is HK$3,303
HK$6,146 total
includes taxes & fees
1 Dec - 2 Dec
Spacious 5-bedroom house in charming Lee with WiFi
Fridge, microwave, oven, stovetop
The Bluebirds Nest

The Bluebirds Nest

Washington Square
7.4 out of 10, Good, (8)
"We were unimpressed with our stay at The Bluebird’s Nest. Outside of quick responsiveness for WiFi details, the experience wasn’t good. The apartment felt lived in with food in the refrigerator and dirty dishes in the dishwasher. There was garbage piled up under the stairs to the front door, electrical boxes with exposed wires and cracks around the tub. The beds and bedding were very uncomfortable (hard, hot and noisy). We would not stay again."
United States
Tim W.
The price is HK$482
HK$982 total
includes taxes & fees
5 Dec - 6 Dec
The Bluebirds Nest
Exterior
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (15)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
United States
Jim O.
The price is HK$4,655
HK$8,634 total
includes taxes & fees
18 Nov - 19 Nov
Hancock Village Inn Near Jiminy Peak
Outdoor banquet area
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!

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)
"The house was very clean and well stocked. There were so many fun things to do - swimming pool, ping pong, darts, air hockey, gym, pinball, basketball hoop, foosball, etc. it was a great house for 4 families. The owner was very communicative and responded quickly to questions about the neighborhood, it was also very well located. Highly recommend!"
United States
Daisy H.
Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

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
Smart TV, books
Chic Madison Parkview

Chic Madison Parkview

Albany
9.6 out of 10, Exceptional, (28)
"Good location and well kept"
United States
Steve J.
The price is HK$692
HK$1,360 total
includes taxes & fees
24 Nov - 25 Nov
Chic Madison Parkview
Property grounds
The Lakeshore House

The Lakeshore House

Niverville
10.0 out of 10, Exceptional, (1)
"Excellent stay!"
United States
KEITARO A.
The price is HK$3,769
HK$6,232 total
includes taxes & fees
14 Nov - 15 Nov
The Lakeshore House
Dining tables
2 bed room Apartment

2 bed room Apartment

South End
10.0 out of 10, Exceptional, (4)
"Clean rooms, comfortable beds. Easy access location. Quiet neighborhood. Would stay again."
United States
Sarah K.
The price is HK$738
HK$1,385 total
includes taxes & fees
16 Nov - 17 Nov
2 bed room Apartment
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.

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

Lenox
9.2 out of 10, Wonderful, (32)
"Beautiful property with tons of space and fantastic for a group of friends or family"
United States
Greg S.
Amore Estate - beautiful room with many places to explore and relax in.
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
9.0 out of 10, Wonderful, (7)
"Family ski trip was made extremely enjoyable by staying at this property. Everything worked out as advertised"
United States
Henry C.
The price is HK$1,251
HK$4,198 total
includes taxes & fees
14 Nov - 15 Nov
Comfortable Berkshires retreat on mtn resort, SISO
Property grounds
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

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.
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 Hotel Reviews

Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

10/10 Excellent
"Great experience "
Kwasi 1-night trip
Posted 2 days ago
Hampton Inn & Suites Albany-Downtown

Find out more about Stephentown

Search for holiday rentals in Stephentown on Expedia! You can easily find your home rentals, villas, holiday apartments in Stephentown using one of the methods below:

  • View our selection of featured holiday rentals in Stephentown
  • Use the map to find apartments and other holiday homes in the Stephentown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Stephentown while they last

Look no further and take a look at our great range of rental properties in Stephentown!

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?

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!: This holiday home rental outside of Stephentown offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a fridge, a stovetop and a coffee maker, so that you can cook with friends or family. You can relax into your holiday with a garden and table football.

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?

Family-friendly attractions include Zema's Nursery, whereas Taconic Ridge State Forest is a spot to enjoy the outdoors. 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.