Stephentown holiday rentals

We found 370 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in Stephentown that are perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as Wi-Fi and a washer and dryer. At the end of the day, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Stephentown

Showing deals for:13 Nov - 20 Nov

Renovated kitchen
Outdoor dining
Interior
Dining
Exceptional
(39 reviews)

Large, family-friendly farmhouse located in the beautiful Berkshires

Williamstown

20% off
AU$6,177
for 7 nights, 1 home
AU$882 per night
includes taxes & fees
Large, family-friendly farmhouse located in the beautiful Berkshires
Property grounds
Private kitchen
Private kitchen
Interior
Exceptional
(5 reviews)

Dog Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak

Williamstown

20% off
AU$2,935
for 7 nights, 1 room
AU$419 per night
includes taxes & fees
Dog Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak
Dining Room w/ Doors to Screened Porch Dining Area
Fully screened porch!
Kitchen with stainless steel appliances
Reading nook with natural lighting
Exceptional
(7 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond

12% off
AU$5,423
for 7 nights, 1 home
AU$775 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Living area
Terrace/patio
Private kitchen
Room
Exceptional
(20 reviews)

Family-friendly, private three bedroom cottage in the beautiful Berkshires

Williamstown

12% off
AU$4,597
for 7 nights, 1 cottage
AU$657 per night
includes taxes & fees
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Interior
Living area
Interior
Exterior detail
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
AU$6,029
for 7 nights, 1 home
AU$861 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
View from the lawn by the water
view from the 2nd bedroom
Open plan dining area with water views and access to the sunroom
Workstation with a view!
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
AU$6,872
for 7 nights, 1 home
AU$982 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Interior
Property grounds
Interior
Exterior
Exceptional
(10 reviews)

Mountain View Retreat in Hudson Valley near Berkshire Attractions

Old Chatham

8% off
AU$2,574
for 7 nights, 1 cottage
AU$368 per night
includes taxes & fees
Mountain View Retreat in Hudson Valley near Berkshire Attractions
Country Inn heated pool & outdoor hot tub is open all year.  Towels are provided
Spring at Jiminy Peak 2019
Night skiing view from living room
View from ski room to trail thru woods to Grouse Run - fantastic location!!
Exceptional
(46 reviews)

Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.

Hancock

12% off
AU$7,938
for 7 nights, 1 home
AU$1,134 per night
includes taxes & fees
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Living area
Interior
Room
Interior
Exceptional
(40 reviews)

A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.

Stephentown

8% off
AU$2,440
for 7 nights, 1 home
AU$349 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.
Main Level Living Area
The Deck at Christiansen's Tavern
The Country Store
Outdoor Pool near The Country Store
Exceptional
(24 reviews)

Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak

Hancock

8% off
AU$7,373
for 7 nights, 1 home
AU$1,053 per night
includes taxes & fees
Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak
Spacious Eat In Kitchen w/  lots of counter space for family/friend meals!
Create your special memories in our Bellavista Barn!
Beautiful Large In-Ground Heated Pool! Complete Privacy!
Enjoy Breakfast at kitchen table overlooking the pool & patios!
Exceptional
(98 reviews)

Incredible Estate: Pool, Pond, Gym, Arcade, Trails & more: Perfect Summer Vacate

Old Chatham

8% off
AU$17,547
for 7 nights, 1 home
AU$2,507 per night
includes taxes & fees
Incredible Estate: Pool, Pond, Gym, Arcade, Trails & more: Perfect Summer Vacate
Interior
BBQ dinner not included :)
Interior
Exterior
Exceptional
(10 reviews)

Family Fun in The Berkshires at Beautiful Hygge House

Richmond

8% off
AU$5,185
for 7 nights, 1 home
AU$741 per night
includes taxes & fees
Family Fun in The Berkshires at Beautiful Hygge House
Entry and living room
Dining
Interior
view into large bathroom
Exceptional
(14 reviews)

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

Richmond

17% off
AU$3,567
for 7 nights, 1 apartment
AU$510 per night
includes taxes & fees
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Beaver Pond Pool/clubhouse
new backyard table
kitchen and laundry room area
another view of same bedroom as well as makeup table
Exceptional
(17 reviews)

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Lanesborough

22% off
AU$5,164
for 7 nights, 1 apartment
AU$738 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Heidi visiting Jane's 18th Century Studio
Interior
Interior
Backside of barn
Exceptional
(99 reviews)

19th c. Barn in the Berkshires

Cheshire

8% off
AU$4,083
for 7 nights, 1 home
AU$583 per night
includes taxes & fees
19th c. Barn in the Berkshires
Smart TV in Downstairs room with view of entrance to house and doors to room
View from 2nd floor balcony (after leaves have fallen)
Views from the back of the 16 acres on the property
Entrance into house with wood burning stove to right and staircase
Exceptional
(72 reviews)

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Williamstown

12% off
AU$3,433
for 7 nights, 1 home
AU$490 per night
includes taxes & fees
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

The charming area of Stephentown awaits your stay

Learn about the unique charm of Stephentown with a stay in a holiday home rental. This romantic city attracts visitors thanks to its skiing and restaurants. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Stephentown

Are you hoping to discover attractions to see while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Stephentown a fun place to get away to. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Jiminy Peak Mountain Resort (5.2 mi / 8.4 km)
  • Waubeeka Golf Links (10.6 mi / 17.1 km)
  • Furnace Brook Winery at Hilltop Orchards (11 mi / 17.7 km)
  • Bousquet Ski Area (11.2 mi / 18.1 km)
  • Kennedy Park (13.4 mi / 21.6 km)
  • Wyndhurst Golf & Club (15.9 mi / 25.7 km)

Exploring the natural features in Stephentown

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Stephentown. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Pontoosuc Lake (8.4 mi / 13.5 km)
  • Mount Greylock State Reservation Visitor Center (9.2 mi / 14.8 km)
  • Queechy Lake (10.2 mi / 16.4 km)
  • Mount Greylock State Reservation (12.4 mi / 19.9 km)
  • Mount Greylock (12.9 mi / 20.8 km)
  • Kennedy Park (13.4 mi / 21.6 km)

Transport to and around Stephentown

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 10.3 mi (16.6 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Hudson, NY (HCC-Columbia County), which is 24.2 mi (38.9 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Stephentown?
Based on our data, houses are considered the most popular property type in Stephentown. But naturally, everyone's idea of the perfect trip is bound to be different. Stayz has holiday homes of all sizes and shapes, and we'll help you to find your ideal match.
How much does it cost to rent a holiday home in Stephentown?
Length of stay, property type and time of year are some things that can affect the price of a holiday home. Simply click on your dates of travel to find your dream escape. From cosy country cottages to expansive villas, all Stayz holiday homes provide incredible value.
How much does it cost to rent a beach house in Stephentown?
Prices for beach houses in Stephentown will vary depending on the size and style of the property and when you plan to travel. Just enter your travel dates into Stayz and how many guests to see available options and prices. From there you can use the filters to refine your search results by ratings, nearby activities and more.
Are there pet-friendly holiday homes in Stephentown?
Good news! Yes. You can pick from six holiday homes that cater to pets in Stephentown. Lots of our pet-friendly holiday homes even come with space outdoors for your fur child to play around in, special dog beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect pad on Stayz.
What are popular home amenities in Stephentown?
The most popular home amenities people look for in Stephentown are a nearby waterfront, a firepit and a barbecue grill. Whether you're travelling with your besties, family or even pets, Stayz holiday homes have the best amenities for starting a new adventure with the people you love.
Are there large group holiday homes in Stephentown?
With five Stephentown properties that can host a group of five or more people, you can bring a few extra family members or pals along. Whether you're planning an informal get-together or a special celebration, we'll help you find the perfect space to fit the occasion.
Are there holiday homes in Stephentown that welcome kids?
Stephentown has six family-friendly holiday homes to choose from. And booking a stay that welcomes children is super easy with Stayz's "Properties good for families" filter. On top of having the whole place to yourselves, you'll also get amenities and perks like living rooms, kitchens and private pools.
What are the top attractions for families in Stephentown?
Arrange a fun family day out at Cherry Plain State Park. This popular attraction is within close proximity of the heart of Stephentown.
Can I find two-bedroom holiday homes in Stephentown?
Gather your family and experience complete comfort and privacy in one of the three two-bedroom holiday homes Stephentown has to offer.
Are there holiday homes with WiFi in Stephentown?
Stephentown has four holiday homes with WiFi, so you can stay connected while travelling. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with your family to sending emails, these Stayz homes make it easy to go online.
How can I find holiday homes with air conditioning in Stephentown?
Stephentown has five holiday homes where you'll be able to spend your days in air-conditioned comfort. To locate a stay on Stayz that features this amenity, enter your desired travel dates and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Stephentown?
Age restrictions can differ between properties on Stayz, so look at the rules of the holiday home in Stephentown you're interested in. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Stephentown for?
The amount of time you can stay in a Stephentown holiday home for differs depending on the property. Just put in your travel dates to see options offering extended stays. They come with the things you need to make your extended holiday more enjoyable and comfortable, such as air conditioning and kitchens. Some properties may also offer discounted weekly or monthly prices, so you can stay longer for less money.