Stockbridge vacation rentals

We found 791 vacation rentals — enter your dates for availability

Discover a selection of 31 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:Jun 19 - Jun 26

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)
  • 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)
  • Jiminy Peak Mountain Resort (18.6 mi / 29.9 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)
  • Tyringham Cobble (5.2 mi / 8.3 km)
  • Lake Mansfield Park (6.2 mi / 9.9 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, Massachusetts, United States of America when booking a vacation rental?
When looking for the best area to stay in Stockbridge, Massachusetts, you might want to consider the charming downtown area. This neighborhood is not only picturesque but is also conveniently located near a variety of attractions. One of the highlights of downtown Stockbridge is the Norman Rockwell Museum, which showcases the iconic works of the beloved American illustrator. Additionally, you can enjoy a stroll through the beautiful gardens of the nearby Berkshire Botanical Garden, which offers a serene escape into nature.

Another great area to consider is the surrounding countryside, where you can find a range of vacation rentals that offer stunning views and a peaceful atmosphere. This area is great for those who appreciate outdoor activities, with opportunities for hiking and exploring the breathtaking landscapes of the Berkshires. The countryside also provides easy access to attractions like Tanglewood, the summer home of the Boston Symphony Orchestra, where visitors can enjoy world-class music in a beautiful natural setting.

In Stockbridge, you'll find a selection of vacation rentals that cater to various preferences, whether you're looking for a cozy cottage or a spacious home.
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 areas for renting a beach house in Stockbridge?
For renting a beach house in Stockbridge, travelers should focus on the beautiful waterfront properties along the scenic Stockbridge Bowl. This picturesque lake offers a range of vacation rentals that provide direct access to swimming, kayaking, and fishing. Many houses in this area come with desirable amenities such as private docks, spacious decks for outdoor dining, and well-equipped kitchens, ideal for families looking to enjoy a lakeside retreat.

In addition to the Stockbridge Bowl, nearby areas around the lake also feature charming cottages and larger homes that often include cozy fireplaces, outdoor fire pits, and serene views of the surrounding mountains. These properties are superb for relaxing after a day of outdoor activities, and some even offer access to community amenities like beaches and hiking trails.

Travelers will also appreciate the proximity to cultural points of interest, such as the Norman Rockwell Museum and Tanglewood, the summer home of the Boston Symphony Orchestra. Rentals in these areas often cater to art enthusiasts and music lovers, providing easy access to events and performances that highlight the rich cultural fabric of the Berkshires. Find your rental near the beach in Stockbridge.
Where are the best Stockbridge ski resort rentals?
For the best ski resort rentals near Stockbridge, Massachusetts, travelers should consider the area around the nearby Butternut Ski Area, which is just a short drive from Stockbridge. In this vicinity, you'll find a variety of cozy cabins and chalets that cater to winter sports enthusiasts. Many properties come equipped with modern amenities such as fully stocked kitchens, fireplaces, and spacious living areas, making them great for families or groups looking to unwind after a day on the slopes.

Additionally, the charming town of Stockbridge itself offers a selection of quaint bed-and-breakfasts and vacation rentals that provide a warm, inviting atmosphere. Many of these accommodations feature historical character, comfortable furnishings, and proximity to local shops and restaurants. Some properties even offer outdoor spaces for relaxation, while others might include hot tubs or saunas for post-ski relaxation.

Travelers can explore not only skiing but also the beautiful landscapes of the Berkshires, with opportunities for snowshoeing and cross-country skiing in the area. The rich cultural scene of Stockbridge, including museums and art galleries, adds to the appeal, making it a well-rounded destination for both winter sports and leisure activities.
What is the most popular type of vacation rental accomodation in Stockbridge?
In Stockbridge, vacation houses are the most popular type of rental, with around 22 available throughout the area. These homes typically offer spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking to enjoy the picturesque surroundings. Many of these houses feature outdoor spaces, such as patios or gardens, where guests can relax and take in the serene atmosphere. Additionally, there are several cottages, condos, and apartments available, providing a variety of options for travelers seeking a cozy retreat near attractions like the Norman Rockwell Museum and the beautiful landscapes of the Berkshires.
Are there any family house rentals in Stockbridge?
In Stockbridge, Massachusetts, there are around 19 family-friendly vacation rentals available, making it a great choice for those traveling with kids. The town is known for its stunning natural beauty and cultural attractions, providing families with plenty of options for exploration. Many of the homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play and enjoy the fresh air.

Visitors can explore nearby highlights such as the Norman Rockwell Museum, which celebrates the iconic American artist, or take a stroll through the beautiful gardens at the Berkshire Botanical Garden. Additionally, the area offers access to scenic hiking trails and opportunities for outdoor activities, ensuring that families have a memorable and enjoyable stay.
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 come with pools and hot tubs, making it an excellent destination for travelers seeking relaxation and recreation. This charming town in the Berkshires offers a mix of serene natural beauty and cultural attractions. Many rentals feature private pools set in picturesque backyards, as well as hot tubs that invite guests to unwind after a day of exploration.

Travelers can expect amenities such as fully equipped kitchens, spacious living areas, and outdoor dining spaces, great for family gatherings or socializing with friends. The area's proximity to outdoor activities, including hiking and skiing in the winter months, adds to the appeal of these properties. 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, there are several pet-friendly house rentals available, totaling around 11 options for travelers. This picturesque town, located in the Berkshires, offers a charming atmosphere with easy access to outdoor activities and cultural attractions. Many of these vacation rentals feature amenities such as spacious living areas, fully equipped kitchens, and private outdoor spaces, making them ideal for families or groups traveling with pets.

The area is surrounded by natural beauty, with nearby attractions like the Stockbridge Bowl, where visitors can enjoy hiking and scenic views. Additionally, the Norman Rockwell Museum is a short distance away, showcasing the town's artistic heritage. Stockbridge's quaint downtown area offers pet-friendly cafes and shops, ideal for those traveling with their furry friends.
Are there any remote work vacation rentals in Stockbridge?
In Stockbridge, Massachusetts, there are a variety of remote work vacation rentals available, with around 25 options to choose from. The area is renowned for its picturesque landscapes and rich cultural heritage, making it a delightful place to work remotely. Many of these properties come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated desk spaces, and comfortable desk chairs, ensuring a productive environment.

Travelers can expect additional features that enhance their stay, such as cozy living areas, fully equipped kitchens for preparing meals, and access to outdoor spaces to unwind after a long day of work. The charm of Stockbridge, coupled with its proximity to attractions like the Norman Rockwell Museum and the beautiful scenery of the Berkshires, creates a great balance of work and leisure. 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 fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature decks or patios, providing outdoor spaces to relax and enjoy the serene surroundings. Fireplaces are common, adding a cozy touch for those cooler evenings. Onsite parking is typically available, making it convenient for travelers who arrive by car. Additionally, some rentals come with a blender, superb for whipping up smoothies or cocktails to enjoy while taking in the beautiful views of the Berkshire Mountains.
When is the best time to visit Stockbridge for a vacation rental?
The peak season for vacation rentals in Stockbridge is during the summer months of July to September, when the charming town comes alive with visitors eager to enjoy its cultural offerings and stunning landscapes. July, in particular, is the most popular month, attracting travelers who appreciate the warm weather and vibrant setting, making it an ideal time for outdoor activities like hiking and exploring the beautiful gardens and parks.

During this peak season, you can expect average temperatures in the mid-70s to low 80s Fahrenheit, creating a comfortable environment for sightseeing and outdoor adventures. The picturesque backdrop of the Berkshires enhances your experience, with opportunities to attend local festivals, art shows, and live performances that showcase the region's rich artistic heritage.

If you're looking for a more budget-friendly option, consider visiting in January. This month offers a serene charm as Stockbridge transforms into a winter wonderland, great for cozy retreats and enjoying the peaceful atmosphere. While it may be colder, with temperatures often in the low 30s Fahrenheit, the beauty of the snow-covered landscape provides a great experience for those who enjoy winter activities and quiet exploration.

Ultimately, whether you choose to visit during the lively summer months or the tranquil winter season, Stockbridge has a range of delightful experiences tailored to every traveler's preferences.
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, Massachusetts, United States of America?
In Stockbridge, visitors can immerse themselves in a rich cultural and natural experience. One of the most popular attractions is the Norman Rockwell Museum, located along the banks of the Housatonic River, which showcases the iconic American artist's works and offers a glimpse into the history of illustration. Nearby, the picturesque Main Street is lined with charming shops and eateries, providing a delightful atmosphere for a leisurely stroll.

The Stockbridge Bowl, a beautiful lake surrounded by scenic landscapes, is superb for outdoor activities such as kayaking, swimming, and picnicking. Additionally, the nearby Berkshire Botanical Garden offers a serene setting with diverse plant collections and seasonal displays. For those who appreciate the arts, the Tanglewood Music Center, located a short drive away in Lenox, is the summer home of the Boston Symphony Orchestra and features concerts in a stunning outdoor setting.
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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