Holiday Rentals in Stephentown

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Our top choices for Stephentown holiday rentals

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 €224
includes taxes & fees
12 Apr - 13 Apr
2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers
Stephentown
6.8 out of 10, (3 reviews)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
The price is €251
includes taxes & fees
10 Apr - 11 Apr
Charming 3-bedroom Cabin for nature lovers

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 €475
includes taxes & fees
10 Apr - 11 Apr
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is €475
includes taxes & fees
10 Apr - 11 Apr
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is €287
includes taxes & fees
27 Apr - 28 Apr
BLUSH: Boutique TINY home*private spa*walk to town

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is €320
includes taxes & fees
15 Apr - 16 Apr
Sugar Shack - 300 square feet of pure sweetness.

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (15 reviews)
"My whole experience was just what I needed! Im in love with this place inspired me and my dog was in heaven 💛 "
United States
Lea
The price is €142
includes taxes & fees
12 Apr - 13 Apr
Taborton Harvest Boulder Pines Cabin in the woods

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is €377
includes taxes & fees
14 Apr - 15 Apr
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
The price is €145
includes taxes & fees
10 Apr - 11 Apr
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Florida Mountain Log Cabin

Florida Mountain Log Cabin
Florida
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is €287
includes taxes & fees
13 Apr - 14 Apr
Florida Mountain Log Cabin

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)
"It was great experience and we loved the ammenities."
United States
Carrie C.
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is €321
includes taxes & fees
11 Apr - 12 Apr
Near Tanglewood: Historic Summer Retreat

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, (5 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (12 reviews)
"Room was perfect location for skiing. Able to see slopes and a few of the chairlifts from room. Beds were super comfortable. Parking was close by and in private area which helped avoid parking in huge resort parking lot. Owner was very responsive."
United States
Charles
The price is €239
includes taxes & fees
12 Apr - 13 Apr
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.6 out of 10, Exceptional, (12 reviews)
"wonderful apartment right in town."
United States
Stuart S.
The price is €249
includes taxes & fees
21 Apr - 22 Apr
2-Bdr Apt In Town, By the Water

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

★MODERN 1BR Apt w/ PRIVATE deck! W/D★

★MODERN 1BR Apt w/ PRIVATE deck! W/D★
Arbor Hill
7.8 out of 10, Good, (12 reviews)
"As advertised, great stay, able to walk to dinner and drinks "
United States
Julie B.
The price is €191
includes taxes & fees
10 Apr - 11 Apr
★MODERN 1BR Apt w/ PRIVATE deck! W/D★

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (7 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is €249
includes taxes & fees
26 Apr - 27 Apr
Downtown | Waterfront | Walk to Shops

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"The one-bedroom aparment is spacious, very clean, nice and funtional furniture and a perfectly well equipped kitchen area. Our 2 grandchildren had a fun time. And the apartament is footsteps from the ski lifts - a real treat! I highly recommend it!Ps. And the owner is always at hand, very helpful, and concerned that all is perfect for the guest's stay."
United States
Antonio S.
The price is €241
includes taxes & fees
12 Apr - 13 Apr
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
The price is €241
includes taxes & fees
12 Apr - 13 Apr
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Stephentown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Stephentown holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stephentown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stephentown holiday rentals we have selected for you start as low as €109 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Stephentown rentals

At Expedia, we put the best Stephentown holiday 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 holiday.

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 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?

Sleeps 40 • Heated Pool • Hot Tub • Game Room | Brookside Mountain Retreat: This highly rated holiday home rental in Stephentown is located in a rural location, and has a fireplace, a garden and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a pool table and 1 hot tub.

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 New Lebanon Library.

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.