Housatonic vacation rentals

We found 500 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 27 - Apr 3

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

New Marlborough

8% off
Price is $328
$2,297 for 7 nights
All fees included
Waterfront Cottage 10 Min From Great Barrington

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)
  • 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

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 areas for renting a beach house in Housatonic?
For renting a beach house in Housatonic, Massachusetts, travelers should consider the nearby area of Stockbridge, which is known for its picturesque scenery and proximity to the Housatonic River. The properties along the riverbank offer a serene escape, featuring amenities such as private docks for fishing or kayaking, spacious decks for outdoor dining, and cozy fireplaces for chilly evenings. Many of these rentals also come equipped with modern kitchens and comfortable living areas, making them great for family getaways.

Another great option is the area around Lake Mahkeenac in nearby Becket, where you can find vacation homes that provide access to a lovely sandy beach. These homes often include private beach access, outdoor grills, and gardens, ideal for enjoying summer activities by the water. Visitors can also explore the surrounding nature trails and enjoy hiking and biking in the lush landscapes.

For those interested in cultural attractions, the town of Lenox, just a short drive away, offers rentals that allow easy access to Tanglewood, the summer home of the Boston Symphony Orchestra. Accommodations here often feature charming architecture, outdoor spaces for relaxation, and proximity to local dining and shopping options.
Where are the best Housatonic ski resort rentals?
For ski resort rentals near Housatonic, Massachusetts, travelers should consider the nearby town of Great Barrington, which is approximately a 20-minute drive from the slopes of Butternut Ski Area. In Great Barrington, visitors can find a range of accommodations, including cozy chalets and modern condos that cater to both couples and families. Many of these properties come equipped with amenities such as fireplaces, full kitchens, and outdoor patios, superb for relaxing after a day on the mountain.

Additionally, the neighborhood around Lake Buel offers charming cabins with scenic lake views, ideal for those looking to combine winter sports with serene natural beauty. These rentals often feature amenities like wood-burning stoves, hot tubs, and easy access to both the lake and local hiking trails.

For those looking to explore additional ski options, the town of Lee is also a short drive away, where travelers can find quaint inns and lodges that provide a comfortable base for skiing adventures. Many of these accommodations come with breakfast included, as well as facilities like ski storage and shuttle services to the nearby ski areas, adding convenience for guests.
What is the most popular type of vacation rental accomodation in Housatonic?
In Housatonic, vacation houses are the most popular type of accommodation, with around 10 available for travelers. These houses often feature spacious layouts with multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Many also include outdoor spaces such as patios or gardens, allowing guests to enjoy the natural beauty of the surrounding area. Additionally, there are several cottages that provide a charming and cozy alternative, typically set in scenic locations that offer a peaceful retreat.
Are there any family house rentals in Housatonic?
In Housatonic, Massachusetts, there are several family-friendly house rentals available, making it an excellent choice for groups looking to explore the scenic beauty of the Berkshires. Many properties in this charming area feature spacious living rooms, fully equipped kitchens, and outdoor decks or patios where families can relax together. Some homes even come with amenities like game rooms, fire pits, or access to nearby hiking trails, ensuring plenty of activities for all ages.

Visitors will find that Housatonic is conveniently located near cultural attractions, such as the Norman Rockwell Museum and Tanglewood, which hosts various performances throughout the year. The nearby town of Great Barrington offers additional dining and shopping options, creating a well-rounded experience for families.
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 feature pools and hot tubs. This charming town is located in the scenic Berkshires, known for its beautiful landscapes and cultural attractions. Travelers can find homes with amenities such as private swimming pools, relaxing hot tubs, and spacious outdoor areas great for gatherings or family activities.
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, Massachusetts, there are several pet-friendly house rentals available, great for travelers looking to enjoy the scenic beauty of the Berkshires with their furry companions. Many of these rentals provide cozy amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can roam freely.

The area is known for its proximity to picturesque parks and nature trails, making it an ideal choice for pet owners who enjoy outdoor activities. The nearby Housatonic River offers opportunities for fishing and kayaking, while the surrounding woodlands are great for hiking. Additionally, the charming downtown area features local shops and eateries that welcome pets, ideal for those traveling with their four-legged friends.
Are there any remote work vacation rentals in Housatonic?
In Housatonic, Massachusetts, there are several vacation rentals available that are well-suited for remote work. Many of these properties feature dedicated office spaces complete with desks, chairs, and computer monitors, allowing for a productive work environment. Travelers can expect amenities such as high-speed Wi-Fi, ensuring smooth connectivity for virtual meetings or tasks that require reliable internet access.

The area itself is charming, with picturesque views of the Berkshire Mountains and proximity to local attractions, including hiking trails and cultural sites in nearby towns like Great Barrington. Some rentals may also offer outdoor spaces where you can take breaks and enjoy the fresh air, enhancing your work-from-home experience. 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 WiFi, kitchens, and patios. Many rentals feature well-equipped kitchens, allowing travelers to prepare their own meals, alongside cozy living areas great for relaxing after a day of exploring the nearby attractions. Patios provide outdoor space for guests to unwind and enjoy the fresh air. Additional amenities may include blenders for making smoothies and coffee or tea makers for a warm beverage in the morning.
When is the best time to visit Housatonic for a vacation rental?
January emerges as a popular time to visit Housatonic, drawing nature enthusiasts and those in search of cozy winter escapes. This month often features a blanket of snow, creating a picturesque setting that is great for outdoor activities such as snowshoeing and cross-country skiing. With temperatures typically ranging from the low 20s to mid-30s Fahrenheit, visitors can enjoy the crisp air while exploring the scenic beauty of the Berkshires.

The peak season in Housatonic spans from March to May, when the landscape comes alive with vibrant blooms and mild weather. This is a prime time for travelers looking to indulge in hiking, biking, and exploring the charming local art scene. The trails in the area, including those in nearby state parks, are easily accessible, making it convenient for visitors to enjoy the great outdoors.

For those seeking a more budget-friendly option, February offers an excellent opportunity to experience Housatonic at a lower price point. While this month is considered the low season, it provides a unique chance to appreciate the quiet beauty of winter without the crowds. Plus, the serene atmosphere is ideal for cozying up by a fire, enjoying local cuisine, or taking in the stunning winter landscapes.

Ultimately, your choice of when to visit Housatonic will hinge on your preferences—whether you're drawn to the lively activities of spring or the peaceful charm of winter.
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?
In Housatonic, Massachusetts, visitors can enjoy a variety of attractions that highlight the region's natural beauty and artistic culture. The town is located near the scenic Housatonic River, where outdoor enthusiasts can partake in activities like kayaking and fishing. Nearby, the picturesque Berkshire Mountains offer opportunities for hiking and enjoying breathtaking views.

Art lovers will appreciate the close proximity to the renowned Norman Rockwell Museum in Stockbridge, which celebrates the life and works of the famous American painter. Additionally, the area is rich in cultural experiences, with the Mahaiwe Performing Arts Center in Great Barrington showcasing a variety of performances, including concerts and theater productions.

For those looking to explore the outdoors, the nearby October Mountain State Forest provides trails for hiking, biking, and nature walks, making it a great spot for travelers.
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