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Stephentown Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Stephentown vacation rentals

A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

1. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is ￥22,177
￥42,921 total
includes taxes & fees
Oct 18 - Oct 19
Berkshires Apartment at the Stephentown Hotel
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

2. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is ￥27,856
￥88,719 total
includes taxes & fees
Sep 26 - Sep 27
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

3. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is ￥35,452
￥87,706 total
includes taxes & fees
Oct 8 - Oct 9
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.

4. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
The price is ￥24,448
￥46,170 total
includes taxes & fees
Oct 18 - Oct 19
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A modern kitchen with granite countertops, a central island, and a dining area with a gray sofa.

5. 5 Bed / 3 bath Apt Near Jiminy Peak Berkshires

5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
Stephentown
9.4 out of 10, Exceptional, (6 reviews)
"Great Place, Dillon was a excellent host and was very responsive for all our questions"
United States
Sai Chakravarthy M.
The price is ￥56,753
￥105,034 total
includes taxes & fees
Oct 18 - Oct 19
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

6. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,673 reviews)
"Love this place for a weekend getaway."
United States
Jacob
The price is ￥15,058
￥18,556 total
includes taxes & fees
Sep 27 - Sep 28
Vacation Village in the Berkshires
A snow-covered outdoor area with a fire pit, tables, and chairs.

7. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is ￥16,859
￥36,385 total
includes taxes & fees
Sep 27 - Sep 28
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,153 reviews)
"Clean & comfortable stay"
United States
Robert
The price is ￥12,598
￥17,608 total
includes taxes & fees
Oct 1 - Oct 2
Berkshire Mountain Lodge
A large building with a covered entrance and multiple windows, surrounded by snow-covered ground and parked cars.

9. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Hancock
8.6 out of 10, Excellent, (18 reviews)
"Great stay! Perfect location by the pool and nicely renovated as advertised!"
United States
Matthew B.
The price is ￥16,574
￥35,535 total
includes taxes & fees
Sep 28 - Sep 29
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
A wooden cabin with a porch, a door, and a window.

10. Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (18 reviews)
"This was a dash away and perfect! "
United States
Linda R.
The price is ￥19,784
￥28,987 total
includes taxes & fees
Oct 6 - Oct 7
Taborton Harvest Boulder Pines Cabin in the woods
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

11. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Hancock
9.6 out of 10, Exceptional, (33 reviews)
"The suite was a great. Comfortable, clean and decorated very nicely. Bed was very comfortable with nice linens and pillows. "
United States
Eileen O.
The price is ￥16,574
￥36,067 total
includes taxes & fees
Sep 28 - Sep 29
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

12. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (18 reviews)
"Nice Place"
United States
Tom C.
The price is ￥17,093
￥37,833 total
includes taxes & fees
Sep 27 - Sep 28
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

13. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is ￥11,079
￥32,743 total
includes taxes & fees
Sep 29 - Sep 30
NEW RENO - Chalet-style farm loft near Tanglewood
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

14. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.8 out of 10, Exceptional, (6 reviews)
"Excellent communication with our host and property exactly as described. Easy check in/check out."
United States
Jillian G.
The price is ￥22,574
￥46,671 total
includes taxes & fees
Sep 28 - Sep 29
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
A rustic wooden interior with shelves stocked with various products, a 'Tree-Free' sign, and a section with bottled beverages.

15. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is ￥17,948
￥38,963 total
includes taxes & fees
Sep 27 - Sep 28
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Four people seated at a table with food and drinks, wearing winter sports helmets.

16. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (9 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
The price is ￥16,859
￥37,627 total
includes taxes & fees
Sep 27 - Sep 28
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

17. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
The price is ￥16,574
￥35,535 total
includes taxes & fees
Sep 28 - Sep 29
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

18. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is ￥25,559
￥80,269 total
includes taxes & fees
Sep 27 - Sep 28
Comfortable Berkshires retreat on mtn resort, SISO

19. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (12 reviews)
"We had a great stay here. Clean, well-equipped, great location. Hope to come back again!"
United States
Tricia
The price is ￥20,575
￥45,754 total
includes taxes & fees
Sep 28 - Sep 29
Downtown | Waterfront | Walk to Shops
A white two-story house with a porch, surrounded by trees and a hill.

20. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is ￥33,814
￥72,130 total
includes taxes & fees
Sep 30 - Oct 1
1789 Shaker Farmhouse in Berkshires/Hudson Valley
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Excellent location. Clean and comfortable room. Excellent onsite restaurant built into the hotel."
Andrew 1-night trip
Posted less than an hour ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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:

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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?

Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game Room: This Stephentown vacation home rental is located in a rural location and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 13 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a pool table and a hot tub.

How many vacation rentals are there in Stephentown?

Choose from 7 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.