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Stephentown Vacation Rentals

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
$208 nightly
The price is $222
Oct 12 - Oct 13
Total with taxes and fees
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.
$509 nightly
The price is $565
Oct 8 - Oct 9
Total with taxes and fees
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
$499 nightly
The price is $554
Oct 8 - Oct 9
Total with taxes and fees
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.
$247 nightly
The price is $263
Oct 18 - Oct 19
Total with taxes and fees
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A sign for The Stephentown Hotel with a depiction of a red building and mountains.

5. 2 Bed Berkshire Getaway @ Stephentown Hotel

2 Bed Berkshire Getaway @ Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (7 reviews)
"This place is amazing! It is so clean and updated with lots of amenities! Lots of arcade games in the apartment thatthe whole family enjoyed! It's a quick trip to jimney peak to ski it's just down the road. Great restaurants nearby. Definitely recommend this place."
United States
elizabeth r.
$262 nightly
The price is $279
Oct 18 - Oct 19
Total with taxes and fees
2 Bed Berkshire Getaway @ Stephentown Hotel
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, (2,712 reviews)
"Very pleased with our stay -great place for the family we will G-d willing return"
United States
Denton
$110 nightly
The price is $123
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the Berkshires
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,180 reviews)
"Our visit was very nice. Facilities were beautiful!"
United States
marilyn
$115 nightly
The price is $128
Nov 5 - Nov 6
Total with taxes and fees
Berkshire Mountain Lodge
A snow-covered outdoor area with a fire pit, tables, and chairs.

8. 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.
$256 nightly
The price is $286
Oct 13 - Oct 14
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

9. 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.
$240 nightly
The price is $268
Oct 8 - Oct 9
Total with taxes and fees
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Four people seated at a table with food and drinks, wearing winter sports helmets.

10. 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.
$231 nightly
The price is $258
Oct 8 - Oct 9
Total with taxes and fees
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
A wooden cabin with a porch, a door, and a window.

11. 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.
$165 nightly
The price is $183
Oct 8 - Oct 9
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

12. 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.
$231 nightly
The price is $258
Oct 8 - Oct 9
Total with taxes and fees
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

13. 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.
$231 nightly
The price is $258
Oct 8 - Oct 9
Total with taxes and fees
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

14. 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)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
$204 nightly
The price is $207
Oct 8 - Oct 9
Total with taxes and fees
NEW RENO - Chalet-style farm loft near Tanglewood
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

15. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
$256 nightly
The price is $286
Oct 13 - Oct 14
Total with taxes and fees
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A spacious living room with a dining area, a kitchen, and a large window.

16. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
$224 nightly
The price is $227
Nov 2 - Nov 3
Total with taxes and fees
1800s Carriage house in Berkshires / Hudson Valley
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

17. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.6 out of 10, Exceptional, (7 reviews)
"Excellent communication with our host and property exactly as described. Easy check in/check out."
United States
Jillian G.
$287 nightly
The price is $321
Oct 8 - Oct 9
Total with taxes and fees
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Pool

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.
$535 nightly
The price is $542
Oct 8 - Oct 9
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

19. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (19 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
$240 nightly
The price is $270
Oct 26 - Oct 27
Total with taxes and fees
New Studio In Town, By the Water
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

20. 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
$248 nightly
The price is $279
Nov 4 - Nov 5
Total with taxes and fees
Downtown | Waterfront | Walk to Shops
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Very spacious and inviting..Loved the coffee maker in lobby!!!! All the girls at the front desk were extremely nice and welcoming. Very clean property and great location.. to Great Barrington, Lenox, Stockbridge, and Lee with great restaurants near by in those towns as well"
Frank 2-night trip
Posted 2 hours ago
Berkshire Mountain Lodge

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 $123 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.

Explore a world of travel with Expedia

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.