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Housatonic vacation rentals

We found 494 vacation rentals — enter your dates for availability

Discover a selection of 13 homes and other vacation rentals in Housatonic that are perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation homes have the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. You'll be sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Housatonic

Showing deals for:Mar 6 - Mar 13

Image gallery for Waterfront Cottage 10 Min From Great Barrington

Property grounds
10 out of 10, Exceptional, (99 reviews)
Exceptional
(99 reviews)

Waterfront Cottage 10 Min From Great Barrington

Great Barrington, MA

10% off
Price is CA $383
CA $3,445 total
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington

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Find out more about Housatonic

Find the perfect vacation rental for your Housatonic getaway

Experience the unique character of Housatonic with a stay in a vacation home rental. There's no shortage of things to see and do in the area.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 Housatonic

Do you want to find top things to see and do while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that Housatonic has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Kennedy Park (9.4 mi / 15.1 km)
  • Bousquet Ski Area (11.5 mi / 18.5 km)
  • Otis Ridge (14.7 mi / 23.7 km)

Exploring the natural landscape of Housatonic

Whether you're an active traveler or just want to appreciate the scenery, Housatonic is a great spot to appreciate mother nature. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • 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)

Traveling to and around Housatonic

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 11.9 mi (19.1 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 17.5 mi (28.1 km) away.

Frequently asked questions

What is the best area to stay in Housatonic when booking a vacation rental?
When considering a vacation rental in Housatonic, Massachusetts, the area around Main Street is an excellent choice. This charming neighbourhood offers a quaint atmosphere and easy access to local amenities. Staying here provides proximity to the scenic Housatonic River, where visitors can enjoy leisurely walks along the riverbanks or partake in various water activities during the warmer months.

Another appealing spot is the vicinity of the Housatonic Railway, which adds a touch of historical intrigue to your stay. This area is great for exploring the rich heritage of the region, with several properties available that celebrate the town's architectural charm. Additionally, being close to attractions such as the nearby Berkshire Botanical Garden and the Norman Rockwell Museum in Stockbridge enhances the appeal of this locale, offering delightful outings for art and nature enthusiasts alike.
How much does it cost to rent a vacation home in Housatonic?
Prices for vacation 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 travelling 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.
Are there any discounts for Housatonic vacation 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 in Housatonic, Massachusetts, travellers should focus on nearby Great Barrington, which is approximately a 15-minute drive away and offers convenient access to the slopes at Butternut Ski Area. In Great Barrington, visitors can find a variety of rental options, including charming cottages and larger family homes. Many properties feature ski storage, outdoor decks, and fireplaces, providing a warm and inclusive setting after a day on the mountain.

Additionally, the town boasts a vibrant arts scene and a selection of local eateries, enhancing the overall experience for visitors. Rentals often come equipped with modern amenities such as Wi-Fi, fully equipped kitchens, and comfortable living spaces, making them suitable for both short and extended stays.
What is the most popular type of vacation rental accomodation in Housatonic?
In Housatonic, vacation houses are the most popular type of rental accommodation, with around 10 available in the area. These houses typically offer spacious living arrangements, including multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them suitable for families or groups. Additionally, several cosy cottages can be found, providing a quaint and intimate atmosphere for travellers seeking a peaceful retreat. Many of these properties are situated near local attractions, allowing guests to easily explore the scenic beauty of the Berkshires and enjoy outdoor activities.
Are there any family house rentals in Housatonic?
In Housatonic, Massachusetts, there are several family-friendly house rentals available, providing a comfortable base for exploring the picturesque Berkshires. Many of these homes feature spacious living areas ideal for gatherings, fully equipped kitchens for family meals, and outdoor spaces where children can play and enjoy the fresh air.
Can I rent a vacation home with a pool or hot tub in Housatonic?
In Housatonic, Massachusetts, there are several vacation homes available for rent that come with pools or hot tubs, making it an attractive option for travellers looking to relax and unwind. This quaint town, located in the beautiful Berkshires, offers a range of properties that often feature amenities such as private swimming pools, hot tubs, and spacious outdoor areas great for entertaining or enjoying nature.
Can I find long-stay vacation rentals in Housatonic?
A long-stay vacation 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, making it a great choice for travellers looking to enjoy the scenic beauty of the Berkshires with their furry companions. Many of the vacation homes in the area feature amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces like gardens or decks that are great for relaxing after a day of exploration. Some properties may also include features like fireplaces and hot tubs, adding to the comfort of your stay.
Are there any remote work vacation rentals in Housatonic?
In Housatonic, Massachusetts, there are approximately 10 remote work vacation rentals available, making it a suitable destination for those looking to blend work and leisure. Many of these properties are designed with remote workers in mind, offering amenities such as dedicated office spaces, high-speed Wi-Fi, and ergonomic furniture, including desk chairs and computer monitors. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Housatonic vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation 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.
When is the best time to visit Housatonic for a vacation rental?
January is the most popular month to visit Housatonic, as winter enthusiasts flock to this charming town for its picturesque snow-covered landscapes and a variety of outdoor activities. During this time, many visitors enjoy skiing, snowboarding, and snowshoeing in the nearby Berkshires, making it an ideal destination for those seeking adventure in a serene setting.

The peak travel season runs from March to May, when the weather begins to warm up, and the natural beauty of the region comes to life. This period is great for hiking and exploring the stunning trails that wind through the area, allowing you to immerse yourself in the vibrant spring blooms and lush greenery. Temperatures during these months typically range from about 10°C to 20°C, providing a comfortable climate for outdoor activities and sightseeing.

If you're looking for a more budget-friendly option, consider visiting in February. This quieter month offers a unique opportunity to experience the charm of Housatonic without the crowds. You can enjoy the peacefulness of winter walks and take in the tranquil beauty of the snow-blanketed hills, all while benefiting from lower rental rates.
How early should I book a Housatonic vacation rental?
Book your Housatonic 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.
Can I change or cancel my Housatonic home rental booking on Vrbo?
To find Housatonic 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 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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Housatonic 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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