Housatonic vacation rentals

We found 540 vacation rentals — enter your dates for availability

Discover a selection of 10 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:Jun 19 - Jun 26

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 $506
$3,544 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 perfect for skiing, hiking, and other outdoor sports, appealing to adventure enthusiasts.
  • Scenic Beauty: The village is nestled by the picturesque Housatonic River, providing stunning natural surroundings.
  • Cultural Experiences: Explore historic houses and enjoy local art and culture, enriching your visit.
  • Cozy Accommodations: Choose from charming cottages and stylish condos for a comfortable stay.
  • Nearby Attractions: Don't miss nearby Great Barrington for additional adventures and local charm.

Popular types of accommodation in Housatonic

Planning a getaway to Housatonic? You're in for a treat. This charming area boasts a variety of accommodations, including houses, cozy cottages, and stylish condos. Whether you're looking for a family home or a romantic retreat, you'll find plenty of options. Don't forget to explore local favorites like Breakfast Housatonic restaurants for a taste of the community. Dive into our listings and discover the perfect spot for your Housatonic adventure.

  • Houses: The top choice for travelers in Housatonic, offering spacious and comfortable accommodations for families or groups.
  • Condos: A popular option for those seeking modern amenities and a prime location, ideal for couples and small families.
  • Cottages: Charming and cozy, these rentals provide a quaint getaway experience surrounded by nature.
  • Apartments: Conveniently located and fully equipped, perfect for travelers looking for a home-like stay.
  • Cabins: Rustic and inviting, these options provide a unique escape into the beautiful outdoors.**

Top attractions near Housatonic

Housatonic, Massachusetts, is an ideal destination for ski and adventure enthusiasts, offering a mix of historic houses, nature reserves, and state parks. Visitors can enjoy a rich cultural experience while exploring outdoor activities and family-friendly attractions. Don't miss the nearby Great Barrington for additional adventures and local charm. Whether you're traveling solo, with family, or friends, Housatonic promises a memorable vacation filled with exploration and fun.

  • National Shrine of the Divine Mercy: A peaceful and spiritually enriching destination, this shrine offers serene gardens and beautiful architecture, inviting visitors to reflect and meditate.
  • Norman Rockwell Museum: Celebrating the iconic American artist, this museum showcases Rockwell's beloved illustrations and offers insights into his creative process, making it a must-visit for art lovers.
  • The Mount: Once the home of author Edith Wharton, this historic estate features stunning gardens and architecture, providing a glimpse into the literary history of the region.

Things to do recommended for couples

Housatonic offers a charming escape for couples. Enjoy a scenic hike in the nearby mountains, a cozy picnic by the river, or explore local art galleries together. Don't miss a romantic dinner at a quaint restaurant, where you can savor delicious cuisine and share intimate conversations.

Things to do recommended for families

Families visiting Housatonic can enjoy a day at the picturesque Berkshire Botanical Garden, explore the wonders of the Norman Rockwell Museum, and hike the scenic trails of the nearby Monument Mountain, offering stunning views and outdoor fun for everyone.

Things to do recommended for groups

Groups visiting Housatonic can enjoy a scenic hike at Monument Mountain, explore the charming local shops, and savor delicious meals at farm-to-table restaurants. Don't miss the opportunity to relax by the Housatonic River or take part in a guided tour of the nearby Berkshire attractions.

*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

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—be sure to prioritize your preferences in the search. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Housatonic with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Housatonic with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Housatonic: For many families, a trip isn’t truly fulfilling without their furry companions. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and dog beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Housatonic: If you're seeking vacation rentals with discounts 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 rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Housatonic

Housatonic, Massachusetts, is a charming destination perfect for adventure seekers and families alike. Nestled near the picturesque Housatonic River, this small village offers a relaxing atmosphere with friendly locals. Explore the scenic surroundings, indulge in outdoor sports, and enjoy cozy spots that foster romantic moments. Whether you're hitting the slopes or simply unwinding by the water, Housatonic is a delightful getaway that promises memorable experiences for every traveler.

  • Lenox: Located 8 miles from Housatonic, Lenox is a vibrant city known for its rich cultural scene and romantic getaways. Visitors flock here for entertainment-themed experiences, with highlights including live music concerts and theatrical performances. Outdoor enthusiasts can explore the nearby mountains and lakes, while those seeking relaxation can enjoy the serene landscapes. Lenox also hosts various events at its conference venues, making it a hub for both leisure and business travelers.
  • Great Barrington: Just 5 miles from Housatonic, Great Barrington offers a thrilling escape for adventure seekers and sports enthusiasts. This city is famed for its ski fields and resorts, attracting winter sports lovers from all over. The picturesque surroundings include stunning lakes and mountains, perfect for outdoor activities year-round. Great Barrington's vibrant downtown area features charming shops and eateries, making it a great spot to unwind after a day on the slopes.
  • The Berkshires: Situated 13 miles from Housatonic, The Berkshires is a renowned destination for those seeking outdoor adventures and breathtaking scenery. This region is famous for its ski resorts and fields, providing ample opportunities for winter sports. Nature lovers will appreciate the stunning lakes and mountains, as well as the area's extensive hiking trails. The Berkshires also hosts various events and conferences, making it a versatile destination for visitors looking to experience both relaxation and excitement.

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 a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can really pay off, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental.

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, One Key, you can immediately access member discounts and earn OneKeyCash on qualifying reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient place to plan new trips, manage your travel arrangements, or review and organize your reservations. Your saved or booked properties are categorized into Potential, Upcoming, or Current Trips for easy access. To check out the 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)
  • The Bookstore (7.9 mi / 12.8 km)
  • Catamount Ski Area (8.6 mi / 13.9 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, 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.

More Vacation Ideas