Stephentown Vacation Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Vacation Rentals in Stephentown

Charming 3-bedroom Cabin for nature lovers

8.0 out of 10, Very Good, (1)
"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...
The price is ¥20,764
¥44,576 total
includes taxes & fees
Sep 8 - Sep 9
Charming 3-bedroom Cabin for nature lovers

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1991)
"Beautiful location!"
The price is ¥16,037
¥19,537 total
includes taxes & fees
Sep 14 - Sep 15
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (971)
"I loved everything, pretty clean. The play areas are so cool. "
The price is ¥23,540
¥26,293 total
includes taxes & fees
Sep 10 - Sep 11
Jiminy Peak Mountain Resort

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is ¥14,509
¥16,207 total
includes taxes & fees
Sep 10 - Sep 11
Huttopia Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (128)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
The Ponds at Foxhollow

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (12)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is ¥18,506
¥27,115 total
includes taxes & fees
Sep 22 - Sep 23
Taborton Harvest Boulder Pines Cabin in the woods

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
The price is ¥88,682
¥163,997 total
includes taxes & fees
Sep 22 - Sep 23
Hancock Village Inn at Jiminy Peak

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

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox

Spacious 5-bedroom house in charming Lee with WiFi

The price is ¥48,116
¥99,224 total
includes taxes & fees
Sep 22 - Sep 23
Spacious 5-bedroom house in charming Lee with WiFi

The Rizzy Apartment

7.2 out of 10, Good, (7)
"Great time "
The price is ¥23,051
¥31,931 total
includes taxes & fees
Sep 8 - Sep 9
The Rizzy Apartment

The Bluebirds Nest

7.8 out of 10, Good, (6)
"My family stays at a lot of VRBOs and I have never had a host as accommodating and patient as Antonio. He was quick to respond and even came to the VRBO when I locked myself out."
The price is ¥19,854
¥30,555 total
includes taxes & fees
Sep 6 - Sep 7
The Bluebirds Nest

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

9.0 out of 10, Wonderful, (26)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

9.6 out of 10, Exceptional, (90)
"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

Chic Madison Parkview

9.6 out of 10, Exceptional, (25)
"the apartment was in a great location, easy check-in, very simple check-in"
The price is ¥13,229
¥25,991 total
includes taxes & fees
Sep 16 - Sep 17
Chic Madison Parkview

The Lakeshore House

10.0 out of 10, Exceptional, (1)
"Excellent stay!"
The price is ¥71,804
¥118,724 total
includes taxes & fees
Sep 7 - Sep 8
The Lakeshore House

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is ¥23,836
¥70,102 total
includes taxes & fees
Sep 6 - Sep 7
Comfortable Berkshires retreat on mtn resort, SISO

Taborton Harvest Timber Trails Unique cabin experience

10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
The price is ¥18,506
¥27,115 total
includes taxes & fees
Sep 6 - Sep 7
Taborton Harvest Timber Trails Unique cabin experience

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (146)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

2 bed room Apartment

10.0 out of 10, Exceptional, (4)
"Clean rooms, comfortable beds. Easy access location. Quiet neighborhood. Would stay again."
The price is ¥11,844
¥23,984 total
includes taxes & fees
Sep 8 - Sep 9
2 bed room Apartment

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.8 out of 10, Exceptional, (17)
"Very friendly hosts, great location. "
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Stephentown Hotel Reviews

Find out more about Stephentown

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 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?

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table: This vacation home near Stephentown is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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?

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.