Stephentown vacation rentals

We found 369 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 6 homes and other vacation rentals in Stephentown that are perfect for your trip. Vacation homes offer the best amenities for your family, friends, or furry companion, such as a hot tub and garden. At the end of the day, you'll be sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Get rewards you won't find with any other major vacation rental platform

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

The charming area of Stephentown awaits your stay

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

Activities and attractions in and around Stephentown

Do you want to discover things to do in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Stephentown has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Jiminy Peak Mountain Resort (5.2 mi / 8.4 km)
  • Bousquet Ski Area (11.2 mi / 18.1 km)
  • Waubeeka Golf Links (10.6 mi / 17.1 km)
  • Furnace Brook Winery at Hilltop Orchards (11 mi / 17.7 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 an active traveler or just want to spend some time taking in the scenery, Stephentown is a great place to spend some time outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Pittsfield State Forest (5.9 mi / 9.4 km)
  • Mount Greylock State Reservation Visitor Center (9.2 mi / 14.8 km)
  • Mount Greylock (12.9 mi / 20.8 km)
  • Grafton Lakes State Park (15.7 mi / 25.2 km)
  • The Mount (16.1 mi / 25.9 km)
  • Naumkeag Museum (18.7 mi / 30.1 km)

Transportation to and around Stephentown

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 10.3 mi (16.6 km) from the city center. If you can't find a flight that's convenient for your trip, 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 vacation rental 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. Vrbo has vacation rentals of all sizes and shapes, and we'll help you to find your ideal match.

How much does it cost to rent a vacation rental in Stephentown?

Length of stay, property type and time of year are some things that can affect the price of a vacation home. Simply click on your dates of travel to find your dream escape. From cozy country cottages to expansive villas, all Vrbo vacation rentals 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 Vrbo 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 vacation rentals in Stephentown?

Good news! Yes. You can pick from six vacation rentals that cater to pets in Stephentown. Lots of our pet-friendly vacation rentals 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 Vrbo.

What are popular rental amenities in Stephentown?

The most popular rental amenities people look for in Stephentown are a nearby waterfront, a firepit and a barbecue grill. Whether you're traveling with your besties, family or even pets, Vrbo vacation homes have the best amenities for starting a new adventure with the people you love.

Are there large group vacation rentals 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 vacation rentals in Stephentown that welcome kids?

Stephentown has six family-friendly vacation rentals to choose from. And booking a stay that welcomes children is super easy with Vrbo'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 vacation rentals in Stephentown?

Gather your family and experience complete comfort and privacy in one of the three two-bedroom vacation homes Stephentown has to offer.

Are there vacation rentals with WiFi in Stephentown?

Stephentown has four vacation rentals with WiFi, so you can stay connected while traveling. 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 Vrbo homes make it easy to go online.

How can I find vacation rentals with air conditioning in Stephentown?

Stephentown has five vacation rentals where you'll be able to spend your days in air-conditioned comfort. To locate a stay on Vrbo 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 vacation rental in Stephentown?

Age restrictions can differ between properties on Vrbo, so look at the rules of the vacation rental in Stephentown you're interested in. But normally, it's 16, 18 or 21.

More Vacation Rentals ideas

People also search for