Stephentown holiday lettings

We found 407 holiday rentals — enter your dates for availability

Discover a selection of 5 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 Mar - 20 Mar

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10 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)

Best of the Berkshires & Hudson Valley

Canaan, NY

8% off
Price is £3,049
for 7 nights, 1 home
£436 per night
includes taxes & fees
Best of the Berkshires & Hudson Valley

Find spaces that suit your style

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)
  • Pineridge Cross Country Ski Center (10.1 mi / 16.3 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)
  • Waubeeka Golf Links (10.6 mi / 17.1 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:

  • Mount Greylock State Reservation Visitor Center (9.2 mi / 14.8 km)
  • Brodie Mountain (9.5 mi / 15.3 km)
  • Queechy Lake (10.2 mi / 16.4 km)
  • Lenox Mountain (11.5 mi / 18.4 km)
  • Lenox Mountain Reserve (11.9 mi / 19.1 km)
  • Pleasant Valley Wilderness Sanctuary (12.2 mi / 19.6 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 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 holiday rentals of all sizes and shapes, and we'll help you to find your ideal match.
How much does it cost to rent a holiday rental 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 Vrbo holiday 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 holiday rentals in Stephentown?
Good news! Yes. You can pick from six holiday rentals that cater to pets in Stephentown. Lots of our pet-friendly holiday 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 travelling with your besties, family or even pets, Vrbo holiday homes have the best amenities for starting a new adventure with the people you love.
Are there large group holiday 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 holiday rentals in Stephentown that welcome kids?
Stephentown has six family-friendly holiday 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 holiday rentals 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 rentals with WiFi in Stephentown?
Stephentown has four holiday rentals 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 Vrbo homes make it easy to go online.
How can I find holiday rentals with air conditioning in Stephentown?
Stephentown has five holiday 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 holiday rental in Stephentown?
Age restrictions can differ between properties on Vrbo, so look at the rules of the holiday rental in Stephentown you're interested in. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental 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.

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