Stephentown vacation rentals

We found 435 vacation rentals — enter your dates for availability

Discover a selection of 5 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.

Vacation rentals with weekly discounts - Stephentown

Showing deals for:Nov 28 - Dec 5

Image gallery for Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !

Room
10 out of 10 rating
Exceptional
(15 reviews)

Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !

Averill Park, NY

9% off
Price is $282
$1,976 for 7 nights
All fees included
Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !

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Find out more about Stephentown

Find out more about Stephentown

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)
  • 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)
  • Wood's Pond (16.2 mi / 26 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:

  • 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 Reserve (11.9 mi / 19.1 km)
  • Pleasant Valley Wilderness Sanctuary (12.2 mi / 19.6 km)
  • Mount Greylock State Reservation (12.4 mi / 19.9 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 best area to stay in Stephentown when booking a vacation rental?
When planning a vacation rental in Stephentown, New York, one of the best areas to consider is near the picturesque Stephentown State Forest. This region offers a serene escape into nature, making it ideal for outdoor enthusiasts. With numerous hiking trails and opportunities for birdwatching, it's superb for those looking to immerse themselves in the natural beauty of the area. Vacation rentals here tend to be cozy cabins or charming homes that provide a tranquil atmosphere, and you can often find a variety of properties to choose from, suiting different group sizes and preferences.

Another great option is to stay closer to the town center, where you can enjoy the local charm and community feel. This area boasts easy access to small shops and eateries, allowing you to experience the quaint lifestyle of Stephentown. The nearby Grafton Lakes State Park is a great attraction, offering swimming, fishing, and extensive trails for hiking and biking. Staying here provides a balance between convenience and a peaceful retreat, making it a popular choice among visitors.
How much does it cost to rent a vacation home in Stephentown?
Prices for vacation rentals in Stephentown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Stephentown to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Stephentown vacation house rentals?
You can find great discounts on house rentals in Stephentown on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Stephentown ski resort rentals?
For skiing near Stephentown, New York, travelers should consider rentals in the nearby town of Pittsfield, which is approximately a 30-minute drive from the nearest ski areas like Bousquet Mountain and Jiminy Peak. In Pittsfield, you can find a variety of accommodations, including cozy cabins and modern condos that cater to ski enthusiasts. Many of these properties feature amenities such as fireplaces, fully equipped kitchens, and outdoor decks, making them ideal for relaxing after a day on the slopes.

Additionally, the town of Lenox, located a bit further away, offers a charming atmosphere with a selection of inns and vacation homes. Many of these rentals are well-appointed with comfortable living spaces, hot tubs, and easy access to local dining options and cultural attractions, such as the Tanglewood Music Center. The proximity to both skiing and the Berkshires' beautiful landscapes allows for a versatile stay that combines outdoor adventure with cultural experiences.
What is the most popular type of vacation rental accomodation in Stephentown?
In Stephentown, vacation houses are the most popular type of rental, with several available throughout the area. These homes typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for comfort and convenience. Many also include outdoor spaces such as decks or patios, allowing guests to enjoy the serene natural surroundings. Additionally, there are several apartments and cabins available, providing further options for travelers seeking different experiences.
Are there any family house rentals in Stephentown?
In Stephentown, New York, there are some family-friendly vacation rentals available, with around 11 options to choose from. This charming area offers a mix of spacious homes, superb for families looking to enjoy the great outdoors together. Many of these properties feature ample living spaces, full kitchens for preparing family meals, and backyard areas where children can play and explore.

Visitors can take advantage of nearby attractions like the beautiful Berkshire mountains, ideal for hiking and outdoor activities, as well as local lakes for swimming and fishing.
Can I rent a vacation home with a pool or hot tub in Stephentown?
In Stephentown, New York, there are several vacation homes available for rent that feature pools and hot tubs, providing travelers with excellent options for relaxation and entertainment. This serene area is known for its picturesque landscapes and proximity to outdoor activities, making it ideal for both families and groups seeking a peaceful getaway.

Many of these rentals come with amenities such as private pools, hot tubs, outdoor decks, and fully equipped kitchens, allowing guests to enjoy both indoor and outdoor living spaces. Some properties may also include features like fire pits and spacious lawns, great for gathering and enjoying the natural surroundings.
Can I find long-stay vacation rentals in Stephentown?
A long-stay vacation rental in Stephentown is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Stephentown?
In Stephentown, New York, there are several pet-friendly house rentals available, offering a variety of amenities to ensure a comfortable stay for travelers and their furry companions. Many of these rentals are situated in scenic locations, providing easy access to outdoor activities such as hiking and exploring nature. Expect to find properties featuring spacious living areas, fully equipped kitchens, and outdoor spaces like decks or yards where pets can roam freely.

The surrounding area is rich in natural beauty, with nearby parks and trails superb for walking dogs and enjoying the outdoors.
Are there any remote work vacation rentals in Stephentown?
In Stephentown, New York, there are several vacation rentals suitable for remote work, with around 11 options available. Travelers can expect properties equipped with essential amenities such as desks, Wi-Fi, and comfortable desk chairs, allowing for a productive work environment while enjoying the serene surroundings. Many of these rentals are situated in peaceful settings, often featuring scenic views of the countryside or nearby forests, providing a tranquil backdrop for focused work sessions.

Additionally, the area offers opportunities for outdoor activities, including hiking and exploring the natural beauty of the surrounding landscape. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Stephentown vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Stephentown with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Stephentown?
In Stephentown, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare meals during their stay. Many rentals also offer WiFi for staying connected and a blender for convenience in making smoothies or drinks. Onsite parking is commonly available, making it easy for travelers with vehicles. Additionally, several properties are pet-friendly, accommodating those who wish to bring their furry companions along for the trip.
How early should I book a Stephentown vacation rental?
Book your Stephentown vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Stephentown?
In Stephentown, visitors can enjoy a range of attractions that highlight the area's natural beauty and outdoor activities. The nearby Taconic State Park offers hiking trails, picnic areas, and stunning views, making it a great spot for nature lovers. For those interested in history, the Stephentown Historical Society provides insights into the local heritage. Additionally, the area is close to the Massachusetts border, allowing easy access to attractions like the Jiminy Peak Mountain Resort, which is popular for both winter sports and summer activities.
Can I change or cancel my Stephentown home rental booking on Vrbo?
To find Stephentown vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Stephentown vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.