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Housatonic holiday lettings

We found 504 holiday rentals — enter your dates for availability

Discover a selection of 12 homes and other holiday rentals in Housatonic that are perfect for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday homes have the amenities that you need and want for your stay, which might include parking and a fireplace. You're sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Housatonic

Showing deals for:2 Jan - 9 Jan

Image gallery for General Williams Estate House Lenox/Stockbridge

Front of house
9.8 out of 10, Exceptional, (110 reviews)
Exceptional
(110 reviews)

General Williams Estate House Lenox/Stockbridge

Stockbridge, MA

8% off
Price is £7,248
for 7 nights, 1 home
£1,035 per night
includes taxes & fees
General Williams Estate House Lenox/Stockbridge

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Find out more about Housatonic

Find out more about Housatonic

Find the perfect holiday rental for your Housatonic getaway

Learn about the unique charm of Housatonic with a stay in a holiday home rental. This city has something for everyone. 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 Housatonic

Do you want to discover attractions to see in the area? Venture out of your holiday home and experience everything that Housatonic has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Ski Butternut (6.2 mi / 10 km)
  • Wyndhurst Golf & Club (7.7 mi / 12.4 km)
  • Catamount Ski Area (8.6 mi / 13.9 km)
  • Furnace Brook Winery at Hilltop Orchards (9.1 mi / 14.6 km)
  • Bousquet Ski Area (11.5 mi / 18.5 km)
  • Hoffman's Pottery (4.4 mi / 7.2 km)

Exploring the natural landscape of Housatonic

Whether you're looking for fun outdoor activities or just want to take in the scenery, Housatonic is a great place to spend some time outside. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Berkshire Botanical Garden (3.2 mi / 5.1 km)
  • Naumkeag Museum (3.4 mi / 5.5 km)
  • Lake Mansfield Park (4.1 mi / 6.6 km)
  • Housatonic River (4.6 mi / 7.5 km)
  • Housatonic River Walk (4.6 mi / 7.5 km)
  • Stockbridge Bowl (5.7 mi / 9.1 km)

Travelling to and around Housatonic

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 11.9 mi (19.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Hudson, NY (HCC-Columbia County), which is 17.5 mi (28.1 km) away.

Frequently asked questions

What is the best area to stay in Housatonic when booking a holiday rental?
When considering a holiday rental in Housatonic, Massachusetts, the best area to stay is near the town centre. This charming neighbourhood offers a delightful mix of local amenities and a picturesque setting. Staying here allows easy access to the delightful shops and eateries that line the streets, providing a true taste of the local culture.

One of the top attractions nearby is the picturesque Housatonic River, which offers scenic views and opportunities for outdoor activities such as kayaking and fishing. Additionally, the historic Housatonic Railroad Depot, an architectural gem, is worth a visit for those interested in local history and railroads.
How much does it cost to rent a holiday home in Housatonic?
Prices for holiday rentals in Housatonic 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 Housatonic 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 Housatonic holiday house rentals?
You can find great discounts on house rentals in Housatonic 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 Housatonic ski resort rentals?
For ski resort rentals near Housatonic, Massachusetts, travellers should consider the nearby town of Great Barrington, which is just a short drive away from the slopes of Jiminy Peak. In Great Barrington, you can find a range of charming holiday homes and stylish condos that often feature amenities like fully equipped kitchens, spacious living areas, and sometimes outdoor hot tubs, making them ideal for relaxing after a day on the mountain.

Another option is the quaint village of Stockbridge, which not only offers proximity to skiing but also a lovely setting with cultural attractions. Here, visitors can find historical homes and modern rentals that typically include comfortable furnishings, fireplaces, and access to local shops and restaurants. The area is also known for its scenic beauty, with properties often featuring views of the surrounding mountains and easy access to winter hiking trails.
What is the most popular type of holiday rental accomodation in Housatonic?
In Housatonic, holiday houses are the most popular type of rental accommodation, with around 10 available throughout the area. These properties typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Additionally, there are several charming cottages scattered around the picturesque neighbourhood, providing a cosy and quaint atmosphere. Many of these rentals also feature outdoor spaces where guests can relax and enjoy the natural beauty of the surrounding Berkshires.
Are there any family house rentals in Housatonic?
In Housatonic, Massachusetts, there are several family-friendly house rentals available, making it a charming destination for those travelling with children. The area offers a variety of spacious properties, many of which feature full kitchens, ample living areas for family gatherings, and outdoor spaces great for kids to run around.
Can I rent a holiday home with a pool or hot tub in Housatonic?
In Housatonic, Massachusetts, there are several holiday homes available for rent that feature pools and hot tubs, providing a great option for those looking to unwind. This quaint town, situated in the scenic Berkshires, offers a peaceful retreat surrounded by nature. Many of the properties you can find here boast amenities such as private pools, hot tubs, and spacious outdoor areas for relaxation and entertainment.
Can I find long-stay holiday rentals in Housatonic?
A long-stay holiday rental in Housatonic is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Housatonic?
In Housatonic, there are several pet-friendly house rentals available, providing a great opportunity for travellers who wish to bring their furry companions along. Many of these accommodations feature amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can roam freely.
Are there any remote work holiday rentals in Housatonic?
In Housatonic, Massachusetts, there are around 10 remote work-friendly holiday rentals available, making it a suitable destination for those looking to blend work with leisure. Many of these properties are equipped with dedicated workspaces, including desks and office chairs, ensuring a comfortable environment for productivity. Additionally, amenities such as Wi-Fi and computer monitors are commonly provided, allowing for seamless connectivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Housatonic holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Housatonic with parking available—perfect for families or travellers 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 Housatonic?
In Housatonic, popular holiday rental amenities include fully equipped kitchens, which are essential for travellers looking to prepare their own meals. Many rentals also feature patios, providing a lovely outdoor space to relax and enjoy the surroundings. Additionally, amenities such as cookware, dishware, and utensils are commonly available, ensuring guests have everything they need for dining in. For added convenience, many properties include dishwashers and microwaves, making meal preparation and cleanup easier.
How early should I book a Housatonic holiday rental?
Book your Housatonic holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Housatonic home rental booking on Vrbo?
To find Housatonic holiday 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 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 travellers 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 cosy 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 Housatonic holiday 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.

More holiday ideas

More holiday ideas