Housatonic vacation rentals

We found 506 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:May 15 - May 22

Image gallery for Best of the Berkshires & Hudson Valley

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

Best of the Berkshires & Hudson Valley

Canaan

9% off
Price is $511
$3,575 for 7 nights
All fees included
Best of the Berkshires & Hudson Valley

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

Find out more about Housatonic

Why visit Housatonic

  • Outdoor adventures: Housatonic is ideal for skiing and exploring its beautiful parks and preserves.
  • Scenic Housatonic River: Enjoy stunning views and relaxing activities along the picturesque river.
  • Historic charm: Discover local historic houses that reflect the area’s rich cultural heritage.
  • Family-friendly ambiance: The welcoming atmosphere makes it perfect for both family outings and romantic getaways.
  • Variety of accommodations: Choose from cozy cottages to modern condos that enhance your stay.

Popular types of accommodation in Housatonic

Planning your getaway to Housatonic? The excitement is just beginning as you choose your perfect retreat. From charming houses and cozy cottages to modern condos, you’ll find an array of options. Enjoy the rustic charm of a Housatonic house with a welcoming outside deck, perfect for relaxing evenings. Plus, you can savor delicious meals at nearby CA restaurants, all while being greeted by friendly staff ready to make your stay memorable.

  • Houses: The top choice for visitors in Housatonic, offering spacious accommodations perfect for families or groups seeking comfort and privacy.
  • Condos: A popular option for those wanting modern amenities and a community feel, ideal for both short and long stays.
  • Cottages: These quaint retreats provide a cozy atmosphere, perfect for a romantic getaway or a peaceful solo retreat.
  • Apartments: A convenient choice for travelers looking for a home-like environment with easy access to local attractions.
  • Cabins: A favorite for nature enthusiasts, offering rustic charm and proximity to the great outdoors.**

Top attractions near Housatonic

Housatonic, Massachusetts, is perfect for outdoor adventures, offering fantastic skiing and exploration opportunities. Visitors can enjoy historic houses, national and state parks, and local preserves, making it an ideal spot for cultural and family experiences. Don't miss the scenic Housatonic River, which adds to the area's charm. Whether you're seeking adventure or relaxation, Housatonic has something for everyone.

  • National Shrine of the Divine Mercy: A serene and inspiring place of worship, this shrine offers a peaceful atmosphere for reflection and prayer, surrounded by beautiful grounds that enhance its spiritual vibe.
  • Norman Rockwell Museum: This art museum showcases the iconic works of Norman Rockwell, capturing American culture and nostalgia through his illustrations, making it a must-visit for art lovers.
  • Berkshire Botanical Garden: A picturesque garden perfect for outdoor strolls, it features diverse plant collections, lovely pathways, and romantic spots, ideal for families and couples seeking tranquility.

Things to do recommended for couples

For a romantic getaway in Housatonic, enjoy a concert at Tanglewood Music Center, just 7 miles away, or hit the slopes at Ski Butternut, 6 miles out. Don't forget to visit Furnace Brook Winery at Hilltop Orchards, 9 miles away, for a charming wine-tasting experience.

Things to do recommended for families

Your family vacation in Housatonic, Massachusetts, can be filled with fun at Lake Mansfield Park, just 4 miles away, offering a peaceful spot for relaxation. Additionally, explore the scenic Tyringham Cobble, located 7 miles away, perfect for enjoying nature and some quality family time.

Things to do recommended for groups

Groups visiting Housatonic can enjoy a scenic hike along the Housatonic River Walk, experience captivating performances at the Mahaiwe Performing Arts Center, and conquer the thrilling zip lines at Catamount Aerial Adventure Park for an unforgettable outdoor adventure.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Housatonic

If you’re planning a trip with friends, family, or pets, or if you're considering a longer stay, be sure to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Housatonic with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Housatonic with young kids: Traveling with young kids can be quite a challenge. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Housatonic: For many families, a getaway wouldn't feel complete without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly homes offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Housatonic: If you’re in search of vacation rentals with great offers for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don’t forget to consider adding amenities like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Housatonic

Housatonic offers a charming escape for adventurers and relaxation seekers alike. With its picturesque backdrop and welcoming atmosphere, visitors can explore quirky spots and enjoy stunning river views. The warmer months present the perfect opportunity for outdoor activities, whether you’re skiing or simply soaking in the scenery. Nearby cities and neighborhoods enhance your experience with family-friendly vibes and romantic settings, making it an ideal destination for a memorable vacation.

  • Lenox: Nestled approximately 8 miles from Housatonic, Lenox is a charming town that offers a blend of culture and leisure. Known for its entertainment and romantic experiences, visitors can enjoy a variety of music concerts and theater performances throughout the year. In winter, Lenox transforms into a winter wonderland with skiing opportunities nearby. The local attractions include beautiful lakes and scenic mountains, which provide the perfect backdrop for outdoor activities. Additionally, Lenox is home to various event and conference venues, making it a great spot for gatherings and celebrations.
  • Great Barrington: Located just 5 miles from Housatonic, Great Barrington is an adventure lover's paradise. This vibrant city is renowned for its skiing and outdoor sports, attracting thrill-seekers year-round. Visitors can explore nearby ski fields and resorts that cater to all skill levels. In addition to winter sports, Great Barrington boasts stunning lakes and breathtaking mountain views, as well as access to the neighboring national state park, perfect for hiking and exploring nature's beauty.
  • The Berkshires: Situated 13 miles from Housatonic, The Berkshires is a picturesque region celebrated for its outdoor adventures and stunning scenery. It’s a dream destination for those looking to immerse themselves in nature, with numerous ski resorts and fields available during the winter months. Beyond skiing, visitors can enjoy the breathtaking views of the mountains and lakes that dot the landscape. The Berkshires also host various events and conferences, making it a versatile destination for both relaxation and recreation.

Best time to go to Housatonic

If you're planning a trip to Housatonic, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in March to August, October and December to January, while off-peak times, like February, September and November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.8°F (-5.1°C)Light RainMostly CloudyModerately HighAverage
February24.8°F (-4.0°C)Light RainMostly CloudyModerately LowAverage
March32.5°F (0.3°C)Light RainMostly CloudyModerately HighSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyModerately HighSlightly Low
May55.9°F (13.3°C)Light RainMostly SunnyModerately HighAverage
June63.7°F (17.6°C)Light RainMostly SunnyModerately HighAverage
July69.8°F (21.0°C)Light RainMostly SunnyModerately HighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnyModerately HighSlightly High
September60.8°F (16.0°C)Light RainMostly SunnyModerately LowAverage
October49.8°F (9.9°C)Light RainMostly SunnyModerately HighSlightly Low
November37.9°F (3.3°C)Light RainMostly SunnyModerately LowAverage
December29.3°F (-1.5°C)Light RainMostly CloudyModerately HighSlightly High

Booking with Vrbo is simple

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Unlock savings with One Key

Reserve an eligible Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner definitely has its perks. When you join our travel rewards program, OneKey, you'll gain immediate access to member discounts and the ability to earn and redeem OneKeyCash on qualifying reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a user-friendly platform where you can easily create new travel plans, resume your previous work, or manage your existing itineraries. You can access the properties you've saved or booked, organized neatly into categories such as Potential, Upcoming, or Current Trips. To begin utilizing Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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)
  • Furnace Brook Winery at Hilltop Orchards (9.1 mi / 14.6 km)
  • Bousquet Ski Area (11.5 mi / 18.5 km)
  • Hudson Chatham Winery (14.1 mi / 22.6 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, Massachusetts, United States of America when booking a vacation rental?
When considering a vacation rental in Housatonic, Massachusetts, the area around the downtown neighborhood emerges as a fantastic option. This charming locale offers easy access to local shops, cafes, and restaurants, creating a vibrant setting for visitors. One of the top attractions nearby is the beautiful Housatonic River, superb for outdoor activities like kayaking and fishing, allowing you to immerse yourself in the area's natural beauty. Additionally, the proximity to the famed Norman Rockwell Museum in Stockbridge, just a short drive away, provides an enriching cultural experience that art lovers will appreciate.

In terms of vacation rentals, the downtown area features a variety of options, making it convenient to find accommodations that suit your needs.
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 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 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 the best ski resort rentals near Housatonic, travelers should consider the nearby town of Great Barrington, which is just a short drive from both Butternut Basin Ski Area and Catamount Ski Area. In Great Barrington, visitors can find a variety of charming vacation rentals, including cozy cabins and spacious homes that often feature amenities such as fireplaces, hot tubs, and outdoor decks with mountain views, great for relaxing after a day on the slopes.

Additionally, the town boasts a vibrant downtown area with local shops and restaurants, providing plenty of options for dining and entertainment. Many properties in this area are equipped with full kitchens, allowing guests to prepare meals and enjoy family gatherings in a comfortable setting.

For those looking for a more rustic experience, the surrounding Berkshires offer properties with scenic views, access to hiking trails, and proximity to lakes for year-round outdoor activities. Some rentals even include communal amenities like fire pits and game rooms, enhancing the overall experience for families and groups.
What is the most popular type of vacation rental accomodation in Housatonic?
In Housatonic, vacation houses are the most popular type of rental, with about 11 available in the area. These homes typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many of these properties also feature outdoor spaces such as decks or gardens, allowing guests to enjoy the scenic surroundings. Additionally, there are several cottages available, which provide a charming and cozy atmosphere for those looking for a more intimate stay.
Are there any family house rentals in Housatonic?
In Housatonic, Massachusetts, there are several family-friendly house rentals available—approximately 11 properties that cater to groups and families. Many of these homes are situated in charming neighborhoods, providing easy access to local attractions and natural beauty. Visitors can enjoy spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces superb for kids to play and explore.

The town's proximity to the picturesque Berkshires enhances the experience, with opportunities for hiking, biking, and enjoying cultural events. Families can also find nearby parks and recreational areas, ensuring plenty of outdoor fun.
Can I rent a vacation home with a pool or hot tub in Housatonic?
In Housatonic, there are several vacation homes available for rent that feature pools and hot tubs, making it an appealing destination for travelers seeking relaxation and recreation. The area is known for its picturesque landscapes and proximity to the Berkshires, where outdoor activities abound. Many of these rentals offer amenities such as private pools, spacious outdoor areas for lounging, and well-equipped kitchens for convenient meal preparation. Some properties may also include hot tubs, creating an ideal setting for unwinding after a day of exploring the beautiful surroundings.
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. 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 Housatonic?
In Housatonic, travelers can find several pet-friendly house rentals that cater to both comfort and convenience. Many of these homes are equipped with essential amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air.

The town's picturesque setting in the Berkshires offers a serene atmosphere, making it an ideal spot for those looking to escape into nature. Nearby, there are plenty of opportunities for outdoor activities, including hiking trails and parks that welcome pets, allowing you to explore the beautiful landscapes with your furry companions.
Are there any remote work vacation rentals in Housatonic?
In Housatonic, Massachusetts, there are several options for remote work vacation rentals, with around 11 available properties. These rentals often come equipped with amenities that cater to remote workers, including dedicated desk spaces and comfortable chairs, ensuring a productive environment. Many properties also feature reliable Wi-Fi, allowing for seamless connectivity during your work hours.

Housatonic itself is a charming town located in the Berkshires, offering a peaceful atmosphere ideal for balancing work and leisure. Nearby attractions include scenic parks and trails, providing opportunities for outdoor activities during breaks. The local community is known for its art scene and quaint shops, adding to the appeal of this destination for those looking to combine work with a bit of relaxation and culture. 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 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 Housatonic?
In Housatonic, popular vacation rental amenities include well-equipped kitchens, allowing travelers to prepare their meals with ease. Many rentals also feature onsite parking, which is convenient for guests with vehicles. Outdoor spaces such as patios and porches or lanais provide a relaxing area for enjoying the fresh air and views of the picturesque surroundings. Additionally, some properties come with a blender, superb for whipping up smoothies or other refreshments during your stay.
When is the best time to visit Housatonic for a vacation rental?
January is a wonderful time to visit Housatonic, especially for those who appreciate a cozy winter getaway. During this month, the serene atmosphere and snow-covered landscapes create a picturesque setting for outdoor activities such as skiing and snowshoeing in the nearby Berkshire Mountains.

As you plan your trip, keep in mind that peak season runs from March to May. This period invites nature enthusiasts and art lovers alike, as the arrival of spring brings blooming flowers and a vibrant arts scene, including the famous Tanglewood Music Festival. Temperatures during these months typically range from the mid-40s to mid-60s Fahrenheit, providing a comfortable climate for hiking and exploring local attractions.

For those looking for more budget-friendly options, February is a fantastic choice. While this month is considered the low season, it offers a unique charm with opportunities for winter sports and peaceful retreats. Visitors can enjoy the quiet beauty of the area and take advantage of reduced rates on vacation rentals, making it an excellent time for a relaxing escape.
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.
What are the top attractions in Housatonic, Massachusetts, United States of America?
In Housatonic, Massachusetts, visitors can explore a variety of attractions that showcase the region's natural beauty and cultural heritage. The picturesque Housatonic River runs through the area, offering opportunities for fishing, kayaking, and scenic walks along its banks. The nearby Berkshire Hills provide stunning views and hiking trails, superb for outdoor enthusiasts.

The town is also close to the historic town of Stockbridge, which is famous for the Norman Rockwell Museum, showcasing the works of the beloved American illustrator. Additionally, the nearby Berkshire Botanical Garden offers a serene environment with beautiful plant displays, making it a lovely spot for a leisurely stroll.

For those interested in arts and culture, the Mahaiwe Performing Arts Center in Great Barrington, not far from Housatonic, hosts a range of performances including music, theater, and film, providing a vibrant local arts scene.
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 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 cabin or a beach condo, 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 as applicable.

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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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.

Frequently asked questions

Can I find vacation rentals in Housatonic?
Yes, there are vacation rentals near the most popular local attractions in Housatonic, or you can choose a more secluded option if you're looking for a relaxing stay.
How many vacation rentals will I find in Housatonic?
Expedia has 12 vacation rentals for your stay in Housatonic.
What's there to see and do in Housatonic?
While exploring the area, visit family-friendly sights like Berkshire Scenic Railway Museum, or get outside and enjoy nature at Housatonic River. Norman Rockwell Museum and Berkshire Botanical Garden are a couple of places you'll find in the larger area.
What's a vacation rental in Housatonic like?
A vacation rental is a private property where you can stay for a few weeks or just a few days in Housatonic. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for family trips.

More Vacation Ideas