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Hinsdale vacation rentals

We found 709 vacation rentals — enter your dates for availability

Discover a selection of 8 homes and other vacation rentals in Hinsdale that are perfect for your trip. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll find the amenities you need and want, which might include a hot tub and a washer and dryer. Whatever you're looking for, you'll be able to choose a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Hinsdale

Showing deals for:May 22 - May 29

Image gallery for Ski at Historic Stone Church in The Berkshires

Interior
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

Ski at Historic Stone Church in The Berkshires

Lanesborough

9% off
Price is $353
$2,470 for 7 nights
All fees included
Ski at Historic Stone Church in The Berkshires

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Find out more about Hinsdale

Why visit Hinsdale

  • Outdoor Adventures: Enjoy a range of outdoor activities, from hiking in nearby mountains to exploring nature preserves.
  • Romantic Getaways: Unwind in cozy vacation homes that offer a perfect setting for couples seeking tranquility.
  • Historic Attractions: Discover local history through historic homes and charming downtown Hinsdale.
  • Family-Friendly Activities: Participate in various activities that cater to families, ensuring fun for all ages.
  • Scenic Campgrounds: Immerse yourself in nature at local campgrounds, ideal for relaxation and exploration.

Popular types of accommodation in Hinsdale

Hinsdale offers a variety of vacation rentals to suit every traveler’s needs. Whether you're looking for houses, cozy cottages, or modern condos, you’ll find the perfect spot for your getaway. Ideal for families or groups, our selection includes spacious house rentals and charming vacation cabins, complete with essential amenities for a comfortable stay. Explore the options and create unforgettable memories in Hinsdale.

  • Houses: The top choice for travelers in Hinsdale, offering spacious and comfortable accommodations perfect for families or groups.
  • Condos: A popular option, these units provide a blend of convenience and amenities, ideal for those seeking a home-away-from-home experience.
  • Cottages: Charming and cozy, cottages in Hinsdale offer a quaint atmosphere for a relaxing getaway.
  • Cabins: Nestled in nature, cabins provide a rustic escape for those looking to unwind.
  • Apartments: Versatile and convenient, apartments are a great choice for couples or solo travelers.**

Top attractions near Hinsdale

Hinsdale, Massachusetts, is perfect for outdoor and romantic getaways, featuring stunning landscapes and a rich cultural experience. Visitors can explore various attractions, including nature preserves, historic homes, and nearby mountains, catering to adventure seekers and history enthusiasts alike. Don't miss the local campgrounds for a chance to immerse yourself in nature and enjoy the serene surroundings. Whether you're seeking relaxation or adventure, Hinsdale has something for everyone.

  • Wahconah Falls State Park: Experience the thrill of adventure amidst stunning natural scenery. This park features beautiful waterfalls, hiking trails, and picturesque landscapes, making it a perfect spot for outdoor enthusiasts and nature lovers.
  • National Shrine of the Divine Mercy: Discover a place of peace and reflection with rich cultural significance. This serene shrine offers a unique spiritual experience, inviting visitors to explore its beautiful grounds and engage in contemplative practices.
  • Berkshire Museum: A family-friendly destination showcasing art, history, and science. Engage with interactive exhibits and enjoy cultural events that inspire curiosity and creativity in visitors of all ages.

Things to do recommended for couples

For a romantic getaway in Hinsdale, enjoy a concert at Tanglewood Music Center, just 11 miles away, or hit the slopes at Jiminy Peak Mountain Resort, 12 miles away. For outdoor adventure, visit Berkshire East Ski Resort, located 18 miles away, and create unforgettable memories together.

Things to do recommended for families

Families vacationing in Hinsdale can unwind at Kennedy Park, just 9 miles away, for relaxation. Thrill-seekers can enjoy the Alpine Super Slide, located 12 miles from town. For a serene experience, Goose Pond Reservation, 11 miles away, offers beautiful landscapes perfect for family picnics and exploration.

Things to do recommended for groups

Groups visiting Hinsdale can enjoy a round of golf at Bas Ridge Golf Course, experience local culture at the Colonial Theater just 7 miles away, and shop for great deals at Lee Premium Outlets, located 11 miles from town, offering a fun day for everyone.

*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 Hinsdale

When traveling with a group, family, or pets, or if you're considering extended stays, it's important to prioritize your preferences when searching. Here are some helpful Vrbo booking tips for you.

  • Traveling to Hinsdale with a group: Take into account how many bedrooms you'll require, as well as features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Hinsdale with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, thinking about how close you are to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Hinsdale: For many families, a vacation wouldn't be the same without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly homes come equipped with feeding bowls and cozy beds, ensuring that all members of your family feel comfortable and at home.
  • Planning for a long term stay visiting Hinsdale: 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 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 Hinsdale

Hinsdale, Massachusetts, is a charming destination perfect for outdoor adventures and romantic getaways. Explore the picturesque downtown Hinsdale, where family-friendly activities abound, or unwind in a cozy vacation home nestled in the scenic surroundings. Nearby attractions offer a blend of relaxation and history, making it ideal for travelers seeking both budget-friendly options and memorable experiences. With its beautiful landscapes and welcoming atmosphere, Hinsdale is sure to be a highlight of your vacation.

  • Lenox: Lenox is a charming city located 10 miles from Hinsdale, known for its vibrant arts scene and natural beauty. Visitors flock to this picturesque town for a variety of experiences ranging from romantic getaways to family-friendly outings. The area is rich in cultural attractions, including music concerts and theater performances, making it a perfect spot for entertainment enthusiasts. Outdoor lovers can enjoy activities like skiing in the nearby mountains or relaxing by the serene lakes. Lenox also hosts notable event venues, making it a hub for conferences and gatherings.
  • Pittsfield: Situated just 7 miles from Hinsdale, Pittsfield is an exciting city that caters to adventure seekers and sports fans alike. Known for its excellent skiing opportunities, the city boasts several ski fields and resorts that are ideal for both beginners and seasoned skiers. Beyond winter sports, visitors can explore local lakes and mountains, perfect for hiking and fishing during warmer months. Pittsfield's vibrant community offers thrilling waterparks and recreational activities, ensuring a fun-filled experience for families and thrill-seekers.
  • Lee: Located 11 miles away from Hinsdale, Lee is a delightful city that offers a mix of romantic and family-oriented experiences. The city's cultural landscape shines through its theaters and music concerts, providing entertaining evenings for visitors. Outdoor enthusiasts will appreciate the beautiful lakes and scenic mountains that surround the area, ideal for hiking or picnicking. Lee is also home to historical monuments, adding a touch of culture to your visit. With its charming atmosphere, Lee is a wonderful destination for creating lasting memories with loved ones.

Best time to go to Hinsdale

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January22.5°F (-5.3°C)Light RainMostly CloudyAverageAverage
February24.3°F (-4.3°C)Light RainMostly CloudyAverageAverage
March32.0°F (0.0°C)Light RainMostly CloudyAverageSlightly Low
April43.9°F (6.6°C)Light RainMostly CloudyHighSlightly Low
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
June63.7°F (17.6°C)Light RainMostly SunnyHighAverage
July69.8°F (21.0°C)Light RainMostly SunnyHighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnyAverageSlightly High
September60.8°F (16.0°C)Light RainMostly SunnyAverageAverage
October49.6°F (9.8°C)Light RainMostly SunnyLowSlightly Low
November37.6°F (3.1°C)Light RainMostly SunnyLowAverage
December29.1°F (-1.6°C)Light RainMostly CloudyLowSlightly High

Booking with Vrbo is simple

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

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash on the full booking amount. Being the organizer really has its perks. Become a member of our One Key rewards program to enjoy exclusive savings and accumulate OneKeyCash on eligible stays. Sign up today and begin reaping the rewards.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient area to plan new adventures, pick up right where you left off, or manage your travel arrangements. You can easily find the properties you've saved and booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Why people love visiting adventurous Hinsdale

Enjoy the history and other features of Hinsdale. Renowned for its golfing, restaurants and shopping, this city welcomes all visitors. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Hinsdale

Are you looking for attractions to visit while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Hinsdale a one-of-a-kind vacation spot. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Bousquet Ski Area (8 mi / 12.9 km)
  • Wyndhurst Golf & Club (9.8 mi / 15.8 km)
  • Jiminy Peak Mountain Resort (11.7 mi / 18.8 km)
  • Furnace Brook Winery at Hilltop Orchards (13.6 mi / 21.9 km)
  • Otis Ridge (16.9 mi / 27.1 km)
  • Berkshire East Ski Resort (17.8 mi / 28.6 km)

Exploring the natural features in Hinsdale

Whether you're looking for adventure or just want to take in the scenery, Hinsdale is a great spot to appreciate mother nature. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Mount Greylock State Reservation Visitor Center (9.1 mi / 14.7 km)
  • The Mount (10.7 mi / 17.3 km)
  • Goose Pond Reservation (11.2 mi / 18.1 km)
  • Stockbridge Bowl (12.2 mi / 19.6 km)
  • Mount Greylock (13.9 mi / 22.4 km)
  • Tyringham Cobble (13.9 mi / 22.4 km)

Traveling to and around Hinsdale

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 8.5 mi (13.7 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Westfield, MA (BAF-Barnes Municipal), which is 28 mi (45 km) away.

Frequently asked questions

What is the best area to stay in Hinsdale, Massachusetts, United States of America when booking a vacation rental?
When considering a vacation rental in Hinsdale, Massachusetts, the area around the town center is an excellent choice. This picturesque neighborhood offers a charming small-town atmosphere while providing convenient access to local amenities. You'll find a variety of properties here, ranging from cozy cottages to more spacious homes, allowing for flexibility depending on your group size and preferences.

One of the top attractions in this area is the scenic Hinsdale Lake, which offers opportunities for fishing, kayaking, and enjoying the natural beauty of the surroundings. Additionally, the nearby Berkshire Scenic Railway Museum provides a fascinating glimpse into the region's history and is a delightful outing for families and history enthusiasts alike.
How much does it cost to rent a vacation home in Hinsdale?
Prices for vacation rentals in Hinsdale 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 Hinsdale 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 Hinsdale vacation house rentals?
You can find great discounts on house rentals in Hinsdale 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 Hinsdale ski resort rentals?
For renting near ski resorts in Hinsdale, Massachusetts, travelers should consider the nearby town of Pittsfield, which is approximately a 30-minute drive from popular skiing areas like Jiminy Peak. In Pittsfield, visitors can find a range of vacation rentals, including cozy cabins and modern condos that typically feature amenities such as full kitchens, fireplaces, and outdoor spaces for relaxing after a day on the slopes.

Additionally, the area surrounding Jiminy Peak offers various lodging options, including lodges and chalets that often provide ski-in/ski-out access, making it convenient for avid skiers. These properties can include features like hot tubs, ski storage, and onsite dining options, enhancing the overall experience for travelers looking for winter adventures.

For those seeking a more rural experience, the town of Lanesborough, located close to the slopes, presents charming cabins and homes set against the backdrop of the Berkshire Mountains. Many of these rentals come equipped with modern comforts and are in proximity to local attractions such as hiking trails and scenic views, making them ideal for both skiers and nature enthusiasts.
What is the most popular type of vacation rental accomodation in Hinsdale?
In Hinsdale, vacation houses are the most popular type of rental, with several available throughout the area. These properties typically feature spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking to enjoy the natural beauty of the Berkshires. Many vacation houses also come with outdoor spaces, such as decks or patios, great for relaxing after a day of exploring local parks and lakes.

Cottages and cabins are also prevalent, with several options offering a quaint, cozy atmosphere. These accommodations often include rustic charm, kitchen facilities, and comfortable furnishings, allowing guests to fully immerse themselves in the serene surroundings. Apartments are another option in Hinsdale, providing a more compact living space with essential amenities, suitable for couples or solo travelers.
Are there any family house rentals in Hinsdale?
In Hinsdale, Massachusetts, there are several family-friendly house rentals available, making it a great option for those traveling with children. This charming locale offers spacious rooms, often featuring multiple bedrooms, full kitchens for preparing meals, and comfortable living areas great for family gatherings. Many properties also provide outdoor spaces, where kids can enjoy playing or families can gather for barbecues.

Visitors can take advantage of the nearby natural attractions, such as the beautiful lakes and hiking trails in the surrounding area, ideal for outdoor adventures. Additionally, the town's close proximity to cultural sites and local parks adds to the appeal for families looking to explore.
Can I find long-stay vacation rentals in Hinsdale?
A long-stay vacation rental in Hinsdale 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 Hinsdale?
In Hinsdale, Massachusetts, travelers can find several pet-friendly house rentals that cater to those looking to enjoy the scenic beauty of the Berkshires. These vacation homes often feature amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can roam. Many properties offer cozy interiors, with fireplaces and comfortable furnishings, making them ideal for relaxing after a day of exploring the area.

Hinsdale is surrounded by beautiful landscapes, providing ample opportunities for outdoor activities with pets. Nearby, the scenic Lake Ashmere offers a tranquil environment for walks and picnics, while the surrounding state forests and parks are great for hiking and enjoying nature.
Are there any remote work vacation rentals in Hinsdale?
In Hinsdale, Massachusetts, travelers will find a selection of remote work vacation rentals available, totaling around 13 options. This charming town, located in the Berkshires, offers a peaceful environment conducive to productivity. Many properties come equipped with essential amenities for remote work, such as reliable Wi-Fi, desk chairs, and dedicated workspaces, ensuring a comfortable and efficient setting for those needing to balance work and leisure.

The area is known for its natural beauty, with easy access to hiking trails and scenic spots great for unwinding after a day of work. Additionally, Hinsdale is close to various attractions, including local parks and cultural sites, allowing for enjoyable breaks in between work commitments. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Hinsdale vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Hinsdale 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 Hinsdale?
In Hinsdale, popular rental amenities include kitchens, patios, and decks or patios, allowing guests to enjoy outdoor spaces and prepare meals at their convenience. Many rentals also come equipped with a blender and a coffee or tea maker, making it easy for travelers to start their day with a fresh beverage. These amenities enhance the home-like experience, enabling visitors to relax and enjoy the natural beauty of the area.
When is the best time to visit Hinsdale for a vacation rental?
The peak travel season in Hinsdale runs from May to July, making it a vibrant time for visitors looking to immerse themselves in the natural beauty and outdoor activities of the Berkshires. July, in particular, stands out as the most popular month, offering warm temperatures (ranging from the mid-50s to the low 80s Fahrenheit) that are superb for hiking, boating, and exploring the scenic landscapes.

During this time, the area comes alive with tourists who are eager to experience the local attractions, including the picturesque lakes and hiking trails that abound in the region. Outdoor enthusiasts will appreciate the opportunity to engage in activities like kayaking on Lake Buel or taking leisurely strolls through the lush, green parks.

For those seeking a more budget-friendly option, consider visiting in October. This month is characterized by stunning autumn foliage, with vibrant reds and golds painting the landscape. It's an ideal time for scenic drives and peaceful hikes, allowing travelers to enjoy the natural beauty without the crowds.
How early should I book a Hinsdale vacation rental?
Book your Hinsdale 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 Hinsdale, Massachusetts, United States of America?
In Hinsdale, Massachusetts, visitors can enjoy the natural beauty and outdoor activities that the area offers. The town is located in the Berkshires, providing easy access to breathtaking landscapes and hiking trails. Nearby, you can explore the scenic Mount Greylock State Reservation, which features the highest peak in Massachusetts and offers stunning panoramic views, especially from the summit.

For those interested in local culture, Hinsdale is close to the charming town of Stockbridge, where attractions like the Norman Rockwell Museum celebrate the famous American painter. The area is also known for its tranquil lakes, such as Ashmere Lake, which is great for swimming, fishing, and kayaking during the warmer months.

Art lovers might consider a short trip to nearby Lenox, home to Tanglewood, the summer home of the Boston Symphony Orchestra, which hosts a variety of concerts and events throughout the season.
Can I change or cancel my Hinsdale home rental booking on Vrbo?
To find Hinsdale 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 Hinsdale 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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