Stephentown Vacation Rentals

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Vacation Rentals in Stephentown

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.
$264 nightly
The price is $293
Nov 12 - Nov 13
Total with taxes and fees
Charming 3-bedroom Cabin for nature lovers

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2132)
"We came here because it was off season, great price, and it had an indoor pool. "
United States
Monica
$112 nightly
The price is $125
Nov 12 - Nov 13
Total with taxes and fees
Vacation Village in the Berkshires

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
$149 nightly
The price is $166
Nov 12 - Nov 13
Total with taxes and fees
Jiminy Peak Mountain Resort

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
$221 nightly
The price is $247
Dec 12 - Dec 13
Total with taxes and fees
Huttopia Berkshires

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (132)
"Perfect location "
United States
krystle
$125 nightly
The price is $140
Dec 5 - Dec 6
Total with taxes and fees
The Ponds at Foxhollow

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.
$165 nightly
The price is $183
Nov 12 - Nov 13
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods

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

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.
$253 nightly
The price is $283
Nov 13 - Nov 14
Total with taxes and fees
Pet Friendly Riverfront Home in Great Barrington

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.
$166 nightly
The price is $179
Nov 19 - Nov 20
Total with taxes and fees
NEW Cozy Apt Bright + Modern W/D

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.
$1,026 nightly
The price is $1,111
Nov 18 - Nov 19
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak

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.
$666 nightly
The price is $743
Nov 18 - Nov 19
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi

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.
$114 nightly
The price is $124
Dec 12 - Dec 13
Total with taxes and fees
The Bluebirds Nest

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.

Chic Madison Parkview

Albany
9.6 out of 10, Exceptional, (28)
"Good location and well kept"
United States
Steve J.
$162 nightly
The price is $175
Nov 13 - Nov 14
Total with taxes and fees
Chic Madison Parkview

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!

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

Stockbridge
10.0 out of 10, Exceptional, (132)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

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.
$535 nightly
The price is $542
Nov 12 - Nov 13
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO

The Lakeshore House

Niverville
10.0 out of 10, Exceptional, (1)
"Excellent stay!"
United States
KEITARO A.
$716 nightly
The price is $802
Nov 12 - Nov 13
Total with taxes and fees
The Lakeshore House

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.
$165 nightly
The price is $178
Nov 13 - Nov 14
Total with taxes and fees
2 bed room Apartment

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

Find out more about Stephentown

Everything you need to know about Stephentown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Stephentown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stephentown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Stephentown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stephentown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Stephentown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $124 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Stephentown rentals

At Expedia, we put the best Stephentown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Stephentown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stephentown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stephentown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!: This vacation home near Stephentown offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and foosball.

How many vacation rentals are there in Stephentown?

Choose from 6 Expedia vacation rentals in Stephentown for a memorable vacation.

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 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.