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Stockbridge vacation rentals

We found 760 vacation rentals — enter your dates for availability

Discover a selection of 30 homes and other vacation rentals in Stockbridge that are perfect for your trip. Whether you're staying in a vacation rental with your kids and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, such as WiFi and cable TV. What you'll find is a rental that has what everyone needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Stockbridge

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

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Find out more about Stockbridge

Why visit Stockbridge

  • Cultural experiences: Explore historic houses and museums that showcase the rich heritage of Stockbridge.
  • Natural beauty: Enjoy scenic nature reserves and serene lakes ideal for outdoor activities and relaxation.
  • Charming town atmosphere: Stroll through the quaint streets filled with unique shops and delightful eateries.
  • Family-friendly adventures: Nearby West Stockbridge offers fun activities suitable for all ages.
  • Diverse accommodations: Choose from cozy cottages, modern condos, and charming inns to suit your vacation needs.

Popular types of accommodation in Stockbridge

Planning a getaway to Stockbridge? The next step is finding the perfect place to stay. Explore popular accommodations like houses, cozy cottages, and modern condos, all conveniently located to help you make the most of your trip. Whether you're looking for a charming home in Stockbridge, a comfortable breakfast inn, or nearby MA hotels, we have options that offer transparency, savings, and peace of mind for your vacation.

  • Houses: The top choice for visitors in Stockbridge, these homes offer ample space and privacy, making them ideal for families and groups.
  • Condos: A popular option for travelers seeking a modern stay, condos provide convenient amenities and a communal atmosphere.
  • Cottages: These quaint and charming rentals offer a cozy escape, perfect for romantic getaways or peaceful retreats.
  • Apartments: Ideal for solo travelers or couples, apartments offer a home-like feel in the heart of Stockbridge.
  • Cabins: For those looking to reconnect with nature, cabins provide a rustic yet comfortable experience surrounded by the great outdoors.**

Top attractions in and around Stockbridge

Stockbridge, Massachusetts, is perfect for a culture-filled, romantic getaway. Visitors can explore historic houses, beautiful nature reserves, and serene lakes, making it an ideal destination for outdoor enthusiasts and families alike. Whether you're seeking cultural experiences or simply want to unwind in nature, Stockbridge offers a charming blend of attractions that cater to all types of travelers.

  • National Shrine of the Divine Mercy: A serene and spiritually enriching site, this shrine offers beautiful gardens and chapels where visitors can reflect and pray. Its tranquil atmosphere and stunning architecture provide a unique cultural experience in the heart of Stockbridge.
  • Norman Rockwell Museum: Dedicated to the iconic American illustrator, this museum showcases his artwork and the creative process behind it. Visitors can explore exhibitions that celebrate Rockwell's storytelling through art, capturing the essence of American life.
  • The Mount: The former home of author Edith Wharton, this historic house features breathtaking gardens and stunning architecture. Located 4 miles away, it provides insight into Wharton's life and work, along with beautiful views of the surrounding landscape.

Things to do recommended for couples

For a romantic getaway in Stockbridge, immerse yourselves in the enchanting sounds at Tanglewood Music Center, just 5 miles away. Enjoy skiing at Ski Butternut, 7 miles from town, or savor exquisite wines at Furnace Brook Winery, located 8 miles away, perfect for a cozy afternoon together.

Things to do recommended for families

Experience family-friendly fun at Lake Mansfield Park, just 6 miles from Stockbridge, where relaxation and wellness await. Alternatively, visit Tyringham Cobble, 5 miles away, for a serene outdoor adventure surrounded by nature's beauty.

Things to do recommended for groups

Groups visiting Stockbridge can enjoy a captivating performance at Shakespeare and Company, explore unique finds at the Berkshire Mountain Country Store, and embark on an adventurous hike along the scenic Housatonic River Walk, perfect for creating lasting memories together.

*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 Stockbridge

If you're planning a trip with friends, family, or pets, or if you're interested in extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Stockbridge with a group: Think about how many bedrooms you require and any additional features you might want, like a full kitchen or outdoor area for group gatherings. Luckily, Vrbo allows you to easily filter for these options and much more.
  • Traveling to Stockbridge with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Stockbridge: For many, a family vacation isn’t truly complete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Stockbridge: If you're in search of vacation rentals that offer great deals for stays of a month or more, you’ve come to the right spot. By using the right filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Stockbridge

Stockbridge, Massachusetts, offers a delightful blend of culture and romance amidst the stunning Berkshire Hills. Explore the charming town, where historical sites and relaxing scenery create a perfect getaway. Nearby, West Stockbridge invites family-friendly adventures and picturesque views. Whether you're seeking entertainment or a serene escape, Stockbridge and its neighboring areas promise a memorable vacation experience filled with warmth and beauty.

  • Lenox: Located 5 miles from Stockbridge, Lenox offers a delightful mix of entertainment, romance, and family-friendly activities. This charming city is known for its vibrant cultural scene, featuring music concerts and theater performances that captivate audiences year-round. Outdoor enthusiasts can enjoy the picturesque landscapes, including nearby lakes and mountains, perfect for hiking and scenic views. Lenox is also home to event venues that host conferences and gatherings, making it a perfect spot for both leisure and business travelers.
  • Great Barrington: Situated 7 miles from Stockbridge, Great Barrington is a haven for adventure and sports lovers, particularly those passionate about skiing. With its proximity to ski fields and resorts, visitors can indulge in thrilling winter sports while enjoying the stunning mountain scenery. The town also boasts a charming downtown area filled with shops and restaurants, inviting travelers to explore local flavors and arts. Nature lovers can venture into nearby national state parks, offering ample opportunities for hiking and outdoor exploration.
  • The Berkshires: About 12 miles from Stockbridge, The Berkshires is renowned for its breathtaking outdoor scenery and adventurous spirit. This region is perfect for those seeking to immerse themselves in nature, with numerous ski resorts and fields catering to winter sports enthusiasts. The stunning landscape features beautiful lakes and mountains, ideal for hiking, fishing, and photography. The Berkshires also hosts various events and conferences, making it a versatile destination for both relaxation and recreation.

Best time to go to Stockbridge

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.8°F (-5.1°C)Light RainMostly CloudySlightly LowAverage
February24.6°F (-4.1°C)Light RainMostly CloudySlightly LowAverage
March32.5°F (0.3°C)Light RainMostly CloudySlightly LowSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May56.3°F (13.5°C)Light RainMostly SunnyAverageAverage
June64.0°F (17.8°C)Light RainMostly SunnyAverageAverage
July70.3°F (21.3°C)Light RainMostly SunnySlightly HighSlightly High
August68.4°F (20.2°C)Light RainMostly SunnySlightly HighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnySlightly HighAverage
October50.0°F (10.0°C)Light RainMostly SunnyAverageSlightly Low
November37.8°F (3.2°C)Light RainMostly SunnyAverageAverage
December29.5°F (-1.4°C)Light RainMostly CloudyAverageSlightly High

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Also, booking an extended stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to narrow down your search by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on the full booking amount. Being the planner has its perks. When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and accumulate OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, keep your travel plans on track, and manage your bookings. Your saved or reserved properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The historic city of Stockbridge awaits you

Enjoy the area's museums, history and architecture and make a vacation rental your home during your stay in Stockbridge. Well-liked for its gardens, camping and hiking, this city is both romantic and relaxing. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Stockbridge

Are you looking for top things to see and do while you're in the area? Venture out of your vacation home and experience everything that makes Stockbridge a one-of-a-kind vacation spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Wyndhurst Golf & Club (4.7 mi / 7.6 km)
  • Kennedy Park (6.8 mi / 10.9 km)
  • Ski Butternut (7.2 mi / 11.6 km)
  • Bousquet Ski Area (9.1 mi / 14.6 km)
  • Catamount Ski Area (11.6 mi / 18.7 km)
  • Otis Ridge (12.9 mi / 20.8 km)

Exploring the natural features in Stockbridge

Whether you're looking for adventure or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Stockbridge. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Naumkeag Museum (0.3 mi / 0.4 km)
  • Berkshire Botanical Garden (1.2 mi / 2 km)
  • Stockbridge Bowl (3.3 mi / 5.3 km)
  • The Mount (3.8 mi / 6.2 km)
  • Housatonic River (6.6 mi / 10.5 km)
  • Housatonic River Walk (6.6 mi / 10.6 km)

Transportation options to and around Stockbridge

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 9.6 mi (15.5 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Hudson, NY (HCC-Columbia County), which is 20 mi (32.3 km) away.

Frequently asked questions

What is the best area to stay in Stockbridge when booking a vacation rental?
When planning a vacation in Stockbridge, Massachusetts, one of the best areas to consider for your stay is the charming downtown area. This picturesque location not only offers a variety of vacation rentals, ranging from cozy cottages to elegant inns, but it also places you close to some of the town's top attractions. A short walk will take you to the Norman Rockwell Museum, where you can immerse yourself in the iconic artist's work and gain insight into his life and inspiration. Additionally, the beautiful Stockbridge Bowl is nearby, providing opportunities for swimming, kayaking, and picnicking amidst stunning natural scenery.

Another appealing option is the area around the Stockbridge Golf Club, which is great for those who enjoy outdoor activities. This neighborhood features lovely rental properties set against a backdrop of lush landscapes and rolling hills.
How much does it cost to rent a vacation home in Stockbridge?
Prices for vacation rentals in Stockbridge 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 Stockbridge 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 Stockbridge vacation house rentals?
You can find great discounts on house rentals in Stockbridge 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 Stockbridge ski resort rentals?
For the best ski resort rentals near Stockbridge, Massachusetts, look towards the nearby town of Lenox and the greater Berkshires region, which offers easy access to popular ski areas like Butternut Basin. In Lenox, travelers can find a variety of charming vacation rentals, including cozy cabins and spacious homes that typically feature amenities such as fireplaces, fully equipped kitchens, and sometimes even hot tubs for relaxation after a day on the slopes.

Staying in the picturesque town of Great Barrington, just a short drive from Stockbridge, provides additional options. Many properties here cater to winter sports enthusiasts, offering amenities such as ski storage, outdoor decks, and proximity to local dining and shopping. This area is known for its vibrant arts scene, making it great for travelers looking to combine skiing with cultural experiences.

The surrounding Berkshires also offer beautiful natural scenery, with hiking trails and scenic parks, making these rentals appealing year-round.
What is the most popular type of vacation rental accomodation in Stockbridge?
In Stockbridge, vacation houses are the most popular rental option, with around 24 available throughout the picturesque town. These homes typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and often cozy living areas that provide a cozy feel. Many vacation houses also come with outdoor spaces, such as porches or gardens, great for relaxing after a day of exploring nearby attractions like the Norman Rockwell Museum and the beautiful landscapes of the Berkshire Mountains.

Additionally, there are several cottages, apartments, condos, and cabins available, suiting a variety of traveler preferences. Cottages and cabins offer a charming, rustic experience, often set in serene locations, while condos and apartments provide convenient access to local amenities.
Are there any family house rentals in Stockbridge?
In Stockbridge, Massachusetts, there are numerous family-friendly house rentals available, with around 18 options to choose from. This charming town is located in the beautiful Berkshires, making it an ideal spot for families looking to enjoy both outdoor activities and cultural experiences. Many of the homes feature spacious living areas, full kitchens that allow for family meals, and outdoor spaces superb for children to play.

Visitors can explore nearby attractions such as the Norman Rockwell Museum, which offers engaging art exhibits suitable for all ages, and the picturesque Stockbridge Bowl for swimming and picnicking. See all family-friendly rentals in Stockbridge.
Can I rent a vacation home with a pool or hot tub in Stockbridge?
In Stockbridge, there are several vacation homes available for rent that feature pools and hot tubs, making it a great choice for travelers seeking relaxation and leisure. This picturesque town in the Berkshires offers a serene environment surrounded by nature, with many properties situated near local attractions and outdoor activities. Travelers can expect amenities such as private pools, inviting hot tubs, spacious outdoor decks, and fully equipped kitchens ideal for enjoying meals with family and friends. Some rentals may also include features like fire pits and gardens, allowing guests to fully embrace the tranquil atmosphere of this charming area. Find your rental in Stockbridge with a pool or a hot tub.
Can I find long-stay vacation rentals in Stockbridge?
A long-stay vacation rental in Stockbridge 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 Stockbridge?
In Stockbridge, Massachusetts, there are several pet-friendly house rentals available, with a total of 11 options to choose from. The area is known for its picturesque landscapes and charming New England architecture, making it a great destination for travelers with pets. Many of these vacation rentals come equipped with amenities such as spacious backyards, fully equipped kitchens, and cozy living areas, superb for relaxing after a day of exploring the surroundings.

Stockbridge is situated near beautiful parks and walking trails, providing ample opportunities for outdoor activities with pets. Nearby, the scenic Edith Wharton Park offers lovely walking paths, picnic areas, and open green spaces, ideal for enjoying a leisurely day out with your furry friends. Additionally, the town is home to pet-friendly cafes and shops, enhancing the overall experience for travelers looking to enjoy a getaway with their pets. See all pet-friendly rentals in Stockbridge.
Are there any remote work vacation rentals in Stockbridge?
In Stockbridge, Massachusetts, there are numerous remote work vacation rentals available, with around 23 options to choose from. This picturesque town, known for its beautiful landscapes and cultural attractions, offers a variety of properties that cater to remote workers. Many of these rentals are equipped with essential amenities such as high-speed Wi-Fi, dedicated desk spaces, and comfortable office chairs, ensuring a productive work environment. Some properties even feature additional items like computer monitors to enhance your setup.

Travelers can expect charming accommodations that blend comfort with functionality, often including cozy living areas and fully equipped kitchens, great for unwinding after a day of work. The scenic surroundings of Stockbridge, with its rich history and artistic heritage, provide excellent opportunities for breaks and relaxation. Nearby attractions include the Norman Rockwell Museum and the beautiful Berkshire Botanical Garden, making it easy to enjoy the local culture and nature when you're not working. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Stockbridge vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Stockbridge 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 Stockbridge?
In Stockbridge, popular vacation rental amenities include kitchens, which allow travelers to prepare their own meals, and WiFi for staying connected. Many rentals also feature coffee and tea makers for a convenient morning routine, blenders for those who enjoy smoothies or other blended drinks, and decks or patios that provide outdoor space for relaxation and enjoying the beautiful surroundings.
When is the best time to visit Stockbridge for a vacation rental?
July marks the peak travel season in Stockbridge, drawing visitors eager to immerse themselves in the vibrant summer atmosphere. With warm weather and lush landscapes, this month offers an array of outdoor activities, including hiking through the picturesque Berkshire Mountains and exploring the charming local art galleries. The lively arts scene and cultural events make it an ideal time for those looking to engage with the community and enjoy summer festivals.

From July through September, travelers can expect a bustling environment filled with fellow vacationers, making it a great opportunity for socializings and shared experiences. The average temperatures during this time typically range from the mid-60s to mid-80s Fahrenheit, creating a comfortable climate for outdoor pursuits and sightseeing in the area.

For those seeking to experience Stockbridge without the summer crowds, consider visiting in January. This month offers a unique charm, with the serene beauty of winter blanketing the landscape. During this time, January provides opportunities for cozy retreats and enjoying the peaceful ambiance of this picturesque town.

Ultimately, the best time to visit Stockbridge depends on whether you favor the energetic summer season filled with activities or the tranquil winter months that allow for introspective exploration and relaxation.
How early should I book a Stockbridge vacation rental?
Book your Stockbridge 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 Stockbridge?
In Stockbridge, visitors can enjoy a range of attractions that highlight the area's natural beauty and cultural heritage. The Norman Rockwell Museum, located in the heart of town, showcases the works of the iconic American artist and offers guided tours of the surrounding gardens. Strolling through the quaint Main Street, travelers can appreciate the historic architecture and visit local boutiques and galleries.

Nearby, the beautiful Stockbridge Bowl is superb for outdoor activities such as hiking, swimming, and picnicking, providing scenic views of the Berkshires. The area is also close to the Berkshire Botanical Garden, which features stunning landscapes and seasonal displays.
Can I change or cancel my Stockbridge home rental booking on Vrbo?
To find Stockbridge 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 Stockbridge 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.

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