Photo by Janine Edmondson

Hinsdale vacation rentals

We found 712 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:Apr 3 - Apr 10

Image gallery for Waterfront Cottage 10 Min From Great Barrington

Property grounds
10 out of 10, Exceptional, (100 reviews)
Exceptional
(100 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
Price is $323
$2,264 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 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)
  • Kennedy Park (8.7 mi / 14 km)
  • Wood's Pond (8.8 mi / 14.2 km)
  • Wyndhurst Golf & Club (9.8 mi / 15.8 km)
  • Jiminy Peak Mountain Resort (11.7 mi / 18.8 km)
  • Otis Ridge (16.9 mi / 27.1 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:

  • Kennedy Park (8.7 mi / 14 km)
  • Wood's Pond (8.8 mi / 14.2 km)
  • Mount Greylock State Reservation Visitor Center (9.1 mi / 14.7 km)
  • Lenox Mountain (9.6 mi / 15.4 km)
  • The Mount (10.7 mi / 17.3 km)
  • Goose Pond Reservation (11.2 mi / 18.1 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 when booking a vacation rental?
When considering a vacation rental in Hinsdale, Massachusetts, the area around the picturesque Lake Ashmere is an excellent choice. This serene neighborhood offers a tranquil retreat with easy access to the lake, where you can enjoy activities such as swimming, kayaking, and fishing. The surrounding natural beauty makes it a superb setting for relaxation and outdoor adventures.

In addition to the lake, Hinsdale is close to the scenic hiking trails of the nearby Pittsfield State Forest, which is a fantastic spot for outdoor enthusiasts. The forest features various trails that cater to different skill levels, allowing you to immerse yourself in the stunning natural landscape.

While vacation rental properties may vary in number, the Lake Ashmere area typically has a good selection of options, ranging from cozy cabins to larger homes, making it suitable for couples, families, or groups of friends.
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 areas for renting a beach house in Hinsdale?
For renting a beach house in Hinsdale, Massachusetts, travelers should explore the beautiful areas surrounding the local lakes, particularly Lake Ashmere and the nearby Berkshire lakes. The properties near Lake Ashmere often come with stunning water views and amenities such as private docks, outdoor seating areas, and fully equipped kitchens, great for families or groups looking to enjoy lakefront living. Many rentals in this area also feature cozy fire pits and spacious decks, ideal for evening gatherings.

In the vicinity, the town of Otis offers additional options, where you can find charming cottages and homes located among the trees, providing a serene escape. Many of these properties include access to private beaches and recreational facilities like kayaks or paddleboards for guests to enjoy the tranquil waters. Additionally, the nearby Becket area presents more rustic accommodations, such as log cabins that offer a secluded feel while still being close to water activities.

For those who appreciate nature, the surrounding Berkshire region provides plenty of opportunities for hiking and exploring. Rentals in this area often come equipped with amenities like outdoor grills, fire pits for roasting marshmallows, and ample space for relaxation, making it a great destination for those looking to enjoy both the lake and the natural beauty of the Berkshires.
Where are the best Hinsdale ski resort rentals?
For ski resort rentals near Hinsdale, Massachusetts, travelers should consider the nearby areas of Pittsfield and Lenox, which are approximately a 20 to 30-minute drive from popular ski destinations such as Jiminy Peak. In Pittsfield, visitors can find a variety of vacation rentals, including cozy cabins and modern apartments, many equipped with amenities like full kitchens, fireplaces, and access to outdoor spaces for relaxation after a day on the slopes.

Lenox offers an enchanting setting with its charming inns and lodges, some of which have luxurious features like hot tubs, heated pools, and proximity to scenic hiking trails in the summer months. The area is also known for its cultural attractions, such as the Tanglewood Music Center and the Norman Rockwell Museum, providing added entertainment options during the off-ski season.

Additionally, travelers looking for a more rustic experience can find rentals in the surrounding hills and forests, where properties often include wood-burning stoves, large decks, and picturesque views of the Berkshires.
What is the most popular type of vacation rental accomodation in Hinsdale?
In Hinsdale, Massachusetts, vacation houses are among the most popular rental options, with several available throughout the area. These houses typically feature multiple bedrooms, spacious living areas, fully equipped kitchens, and outdoor spaces for relaxation, making them ideal for families or larger groups looking to enjoy the natural beauty of the Berkshires. Cabins and cottages are also commonly found, offering a more rustic experience with cozy interiors and often proximity to outdoor activities like hiking or fishing in nearby lakes. Apartments are available as well, providing a comfortable and convenient option for travelers seeking a home base while exploring the charming surroundings.
Are there any family house rentals in Hinsdale?
In Hinsdale, Massachusetts, there are several family-friendly house rentals available, making it a great spot for gatherings. The area is known for its beautiful natural surroundings, with picturesque landscapes and nearby attractions such as the Berkshire Hills and local lakes. Many of these homes offer spacious living areas, full kitchens for preparing family meals, and outdoor spaces superb for children to play. Visitors can also expect amenities like Wi-Fi and cozy indoor setups, ensuring a comfortable stay for everyone.

For those interested in outdoor activities, the nearby Beartown State Forest provides opportunities for hiking, biking, and enjoying nature walks, while the local lakes offer swimming and fishing.
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, there are several pet-friendly house rentals available for travelers looking to enjoy the beautiful scenery of the Berkshires. Many of these rentals offer amenities such as spacious backyards, fully equipped kitchens, and cozy living spaces, making them ideal for families or groups traveling with pets. The homes often feature outdoor areas where pets can roam freely, and some may even include amenities like fire pits or grills for enjoyable evenings outside.

The surrounding area provides ample opportunities for outdoor activities, including hiking and exploring local parks that welcome pets. Nearby, the stunning October Mountain State Forest offers trails and natural beauty for those looking to embark on adventures with their furry companions.
Are there any remote work vacation rentals in Hinsdale?
In Hinsdale, Massachusetts, there are about 14 vacation rentals that cater to remote work needs. These properties typically offer dedicated office spaces, reliable Wi-Fi, and essential office amenities such as desks, desk chairs, and sometimes even computer monitors to create a comfortable work environment. Many rentals are located in serene surroundings, providing a peaceful atmosphere conducive to productivity.

Travelers can also enjoy the natural beauty of the region, with opportunities for hiking and exploring the nearby Berkshire Mountains during breaks from work. The town's charming local shops and restaurants add convenience, ensuring that remote workers can balance their professional commitments with leisure activities. 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 typically include WiFi, kitchens, and patios, which enhance the comfort and convenience of travelers. Many properties come equipped with a blender and a coffee/tea maker, allowing guests to prepare their own meals and enjoy beverages at their leisure.
When is the best time to visit Hinsdale for a vacation rental?
The best time to visit Hinsdale for a vacation rental is during the peak season from May to July, with July being particularly popular among travelers. This vibrant period draws visitors eager to take advantage of the pleasant summer weather, with temperatures ranging from the mid-50s to the high 80s Fahrenheit. Outdoor enthusiasts can enjoy an array of activities such as hiking the scenic trails of the nearby Berkshire Mountains or relaxing by the tranquil lakes in the area.

July especially offers a lively atmosphere, as families and adventure seekers flock to Hinsdale for its beautiful natural surroundings and community events. The longer daylight hours allow for ample opportunities to explore the picturesque landscapes and engage in recreational activities, making it a prime time for those seeking an energetic getaway.

For travelers looking for a more budget-friendly option, October presents an inviting alternative. This month provides a chance to witness the stunning autumn foliage that blankets the region. The crisp air and vibrant colors create a serene backdrop for peaceful walks and scenic drives, all while avoiding the busyness of peak tourist season.

Ultimately, Hinsdale caters to a variety of preferences, whether you're drawn to the bustling summer activities or the quiet charm of fall.
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?
In Hinsdale, Massachusetts, visitors can explore a variety of attractions that highlight the area's natural beauty and outdoor activities. The town is situated near the stunning Berkshire Mountains, offering opportunities for hiking and enjoying scenic views. The nearby October Mountain State Forest features extensive trails and is great for those who appreciate nature and wish to engage in outdoor adventures.

Additionally, the Ashintully Gardens, located a short drive away, provide a peaceful setting with beautifully landscaped grounds and walking paths, making it a lovely spot for leisurely strolls. For those interested in cultural experiences, the town is also close to the historic Norman Rockwell Museum in Stockbridge, showcasing the work of the iconic American artist.

The charming downtown area of Hinsdale offers quaint shops and local eateries, contributing to a pleasant small-town atmosphere that visitors can enjoy.
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.

More Vacation Ideas