Stephentown Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Stephentown holiday rentals

3.0 star property
The price is HK$1,533
HK$4,329 total
includes taxes & fees
26 Feb - 27 Feb
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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 HK$1,212
HK$2,500 total
includes taxes & fees
26 Feb - 27 Feb
Charming 3-bedroom Cabin for nature lovers
8.0 out of 10, Very good, (1 review)
"excellent communication with property manager."
United States
Nancy H.
The price is HK$1,369
HK$4,398 total
includes taxes & fees
11 Mar - 12 Mar
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Camping in Williamstown

Huttopia Berkshires
1.0 star property
9.4 out of 10, Exceptional, (9 reviews)
"Healthy food too!"
United States
GEORGINA
The price is HK$1,317
HK$1,471 total
includes taxes & fees
16 Mar - 17 Mar
Huttopia Berkshires
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 HK$1,478
HK$2,514 total
includes taxes & fees
11 Mar - 12 Mar
BLUSH: Boutique TINY home*private spa*walk to town
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 HK$1,447
HK$2,523 total
includes taxes & fees
3 Mar - 4 Mar
Sugar Shack - 300 square feet of pure sweetness.
10.0 out of 10, Exceptional, (13 reviews)
"Loved this cabin! The communal building is very clean & bathrooms are spotless. There is a farm stand near the entrance where you can buy firewood and fresh eggs. Trails are literally connected to the property for easy nature walks. We plan on coming back!"
United States
Abby L.
The price is HK$977
HK$1,432 total
includes taxes & fees
26 Feb - 27 Feb
Taborton Harvest Boulder Pines Cabin in the woods

Holiday Home in Florida

Florida Mountain Log Cabin
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 HK$1,437
HK$2,667 total
includes taxes & fees
26 Feb - 27 Feb
Florida Mountain Log Cabin
The price is HK$1,408
HK$2,403 total
includes taxes & fees
2 Mar - 3 Mar
3-bedroom house in beautiful Berkshires, close to amenities!
10.0 out of 10, Exceptional, (8 reviews)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
United States
SteveS
The price is HK$1,942
HK$3,501 total
includes taxes & fees
26 Feb - 27 Feb
Treat yourself at the stunning June Farms Wellness Huts!
9.8 out of 10, Exceptional, (6 reviews)
"Such an amazingly unique property with a wonderfully homey feel! While Troy has some not so great parts, we felt reasonably comfortable and safe here. It's amazing to have the Hudson right by on."
Canada
Rachel H.
The price is HK$669
HK$1,628 total
includes taxes & fees
26 Feb - 27 Feb
Riverfront rustic mansion house
10.0 out of 10, Exceptional, (29 reviews)
"We enjoyed our stay "
United States
Lydia T.
The price is HK$528
HK$1,117 total
includes taxes & fees
26 Feb - 27 Feb
Getaway Near Mass MoCA, Great Hiking, Scenic Views
3.0 star property
8.8 out of 10, Excellent, (2,265 reviews)
"Excellent location and terrific space and amenities."
United States
Michelle
The price is HK$813
HK$994 total
includes taxes & fees
26 Feb - 27 Feb
Vacation Village in the Berkshires

Apartment in Williamstown

2-Bdr Apt In Town, By the Water
9.6 out of 10, Exceptional, (12 reviews)
"Clean, close to town, very convenient. On a busy road, so just be aware of that. But overall a good place to stay. "
United States
Brian L.
The price is HK$938
HK$2,216 total
includes taxes & fees
2 Mar - 3 Mar
2-Bdr Apt In Town, By the Water

Apartment in Williamstown

Downtown | Waterfront | Walk to Shops
10.0 out of 10, Exceptional, (7 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is HK$1,016
HK$2,252 total
includes taxes & fees
4 Mar - 5 Mar
Downtown | Waterfront | Walk to Shops
10.0 out of 10, Exceptional, (5 reviews)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is HK$821
HK$1,818 total
includes taxes & fees
3 Mar - 4 Mar
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
9.4 out of 10, Exceptional, (9 reviews)
"Very nice place."
United States
verna A.
The price is HK$802
HK$1,609 total
includes taxes & fees
26 Feb - 27 Feb
★MODERN 1BR GREAT Location Downtown! W/D Parking!★

Holiday Home in Great Barrington

Family Ski Getaway in the Berkshires
9.0 out of 10, Wonderful, (11 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,583
HK$2,476 total
includes taxes & fees
26 Feb - 27 Feb
Family Ski Getaway in the Berkshires

Holiday Home in Williamstown

North Getaway Cottage
9.2 out of 10, Wonderful, (24 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is HK$1,583
HK$3,507 total
includes taxes & fees
26 Feb - 27 Feb
North Getaway Cottage

Apartment in South End

2 bed room Apartment
8.8 out of 10, Excellent, (8 reviews)
"Clean rooms, comfortable beds. Easy access location. Quiet neighborhood. Would stay again."
United States
Sarah K.
The price is HK$743
HK$1,394 total
includes taxes & fees
1 Mar - 2 Mar
2 bed room Apartment
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

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 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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Stephentown is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Stephentown?

Choose from 7 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 Hancock Shaker Village.

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.