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Hinsdale holiday lettings

We found 709 holiday rentals — enter your dates for availability

Discover a selection of 8 homes and other holiday rentals in Hinsdale that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and a washer and dryer. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Hinsdale

Showing deals for:22 May - 29 May

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

8% off
Price is £2,068
for 7 nights, 1 room
£295 per night
includes taxes & fees
Ski at Historic Stone Church in The Berkshires

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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 holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Hinsdale

Are you hoping to discover attractions to visit while you're in the area? Venture out of your cosy holiday rental and experience everything that Hinsdale has to offer. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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 spend some time taking in the scenery, Hinsdale is a great place to get outside. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Travelling to and around Hinsdale

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 8.5 mi (13.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying 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 holiday rental?
When considering the best area to stay in Hinsdale, Massachusetts, you might want to explore the charming neighbourhoods that offer a delightful blend of natural beauty and local attractions. One particularly appealing area is the vicinity around the town centre, which boasts a number of holiday rentals that are both comfortable and conveniently located. This area not only provides easy access to the stunning landscapes of the Berkshires but also places you within a short distance of top attractions such as the picturesque Hinsdale Lake, great for leisurely walks and outdoor activities.

Additionally, the surrounding countryside is dotted with quaint shops and local eateries that truly capture the essence of small-town New England. Staying in this central area allows you to immerse yourself in the community's warm hospitality while enjoying the tranquillity that Hinsdale has to offer.
How much does it cost to rent a holiday home in Hinsdale?
Prices for holiday 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 holiday 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, your best options are near the beautiful shores of nearby lakes, particularly Crystal Lake and the surrounding areas. While Hinsdale itself is more of a rural town, the charm of lakeside living can be found just a short drive away. Lakeside properties often come with amenities such as private docks, outdoor seating areas, and fire pits, which are great for enjoying warm summer evenings by the water.

In the vicinity of Crystal Lake, you can expect to find cosy cottages and larger family homes equipped with fully functional kitchens and spacious living areas, ideal for gatherings. Many properties here also provide access to activities like kayaking, fishing, and swimming, allowing guests to fully embrace the outdoor lifestyle.

Additionally, nearby towns such as Dalton and Cheshire offer further rental opportunities, often featuring properties with scenic views and proximity to local parks and nature trails. These rentals may include amenities like barbecues, picnic areas, and easy access to hiking paths, making them great for those who enjoy both relaxation and adventure in a picturesque setting.
Where are the best Hinsdale ski resort rentals?
For ski resort rentals near Hinsdale, Massachusetts, travellers should consider the charming town of Adams, which is located just a short drive away from the popular ski area of Jiminy Peak. This resort offers a variety of accommodations, including convenient mountain lodges and cosy chalets that are superb for families and groups. Many properties here feature amenities such as ski-in/ski-out access, fully equipped kitchens, and spacious living areas, ensuring a comfortable stay after a day on the slopes.

In addition to Adams, the nearby town of Williamstown also provides excellent rental options. Visitors can find quaint cottages and larger homes that often come with outdoor spaces for enjoying the beautiful Berkshire scenery. These rentals frequently include modern conveniences like Wi-Fi, laundry facilities, and fireplaces, ideal for unwinding after an active day. The proximity to local restaurants and shops in both towns adds to the appeal for those looking to explore the area beyond skiing.

Moreover, the scenic landscapes surrounding Hinsdale offer opportunities for snowshoeing and cross-country skiing, with various trails accessible from many rental properties.
What is the most popular type of holiday rental accomodation in Hinsdale?
In Hinsdale, holiday houses are the most popular type of holiday rental, with around 12 available in the area. These houses typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Additionally, several cottages and cabins can be found, offering a charming, rustic atmosphere and often including amenities such as outdoor fire pits and private gardens for enjoying the natural surroundings. There are also several apartments available, which provide a convenient and homely base for visitors exploring the scenic beauty of Hinsdale.
Are there any family house rentals in Hinsdale?
In Hinsdale, Massachusetts, there are several family-friendly house rentals available, making it a great retreat for those travelling with children. Many of these properties are located in peaceful neighbourhoods, offering spacious living areas and full kitchens, superb for preparing family meals. Visitors can also expect amenities such as private backyards for outdoor activities and comfortable sleeping arrangements suitable for larger groups.

The area is close to outdoor attractions, including nearby lakes and hiking trails that provide ample opportunities for family adventures. Whether it's a day spent fishing, boating, or exploring nature, Hinsdale offers a serene environment for families to enjoy.
Can I find long-stay holiday rentals in Hinsdale?
A long-stay holiday rental in Hinsdale is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Hinsdale?
In Hinsdale, Massachusetts, there are several pet-friendly house rentals available, making it an attractive destination for travellers with furry companions. The area offers a variety of holiday homes that typically feature amenities such as spacious backyards, fully equipped kitchens, and comfortable living spaces, ideal for families or groups looking to relax in a serene setting.

Nestled amid the scenic landscapes of the Berkshires, these rentals provide easy access to numerous outdoor activities. Nearby points of interest include the picturesque lakes and hiking trails that the region is known for, allowing guests to enjoy nature walks and recreational opportunities with their pets.
Are there any remote work holiday rentals in Hinsdale?
In Hinsdale, Massachusetts, there are numerous remote work-friendly holiday rentals available, with around 26 options to choose from. This picturesque town offers a serene environment ideal for those looking to balance work and leisure. Many properties are equipped with essential amenities for remote work, including dedicated desks, Wi-Fi access (often for an additional fee), and comfortable seating arrangements, ensuring a productive workspace.

Hinsdale's location is advantageous for outdoor enthusiasts, with nearby attractions such as the scenic Berkshire Mountains and the charming towns of the Berkshires, offering opportunities for hiking, exploring nature, and enjoying local culture during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Hinsdale holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Hinsdale with parking available—perfect for families or travellers 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 holiday rental amenities typically include a fully equipped kitchen, allowing guests to prepare their own meals during their stay. Many properties also feature outdoor areas such as patios or decks, superb for enjoying the tranquil surroundings. Additional conveniences like blenders and coffee or tea makers are commonly found, enhancing the comfort and functionality of these rentals.
When is the best time to visit Hinsdale for a holiday rental?
The peak season for visiting Hinsdale falls between May and July, with July being the most popular month. This vibrant time of year attracts travellers seeking outdoor adventures, including hiking and fishing in the picturesque Berkshire Mountains. With warm temperatures averaging between 15 to 30 degrees Celsius, it's the great climate for exploring the stunning landscapes and enjoying activities like kayaking on nearby lakes.

July also brings a lively option to the area, with many events and festivals that celebrate local culture and arts, making it an exciting time to experience the community spirit. Whether you're wandering through charming local shops or enjoying a scenic picnic, the summer months offer ample opportunities for relaxation and exploration.

For those looking for a more budget-friendly experience, consider visiting in October. This month showcases the breathtaking autumn foliage, allowing visitors to take in the vibrant colours of the changing leaves. The cooler temperatures can be refreshing, averaging around 5 to 15 degrees Celsius, ideal for leisurely hikes and scenic drives without the summer crowds.

Ultimately, your choice of when to visit Hinsdale will depend on your preference for a bustling holiday filled with activities or a more tranquil getaway immersed in nature's beauty.
How early should I book a Hinsdale holiday rental?
Book your Hinsdale holiday 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 holiday 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 enjoy a variety of attractions that highlight the area's natural beauty and local culture. The nearby Beartown State Forest offers an array of outdoor activities, including hiking trails that wind through scenic landscapes and opportunities for wildlife viewing. The forest is a popular destination for nature enthusiasts looking to explore the rich flora and fauna of the region.

Additionally, the quaint town centre features charming local shops and eateries where visitors can experience the community's warm hospitality. For those interested in history, the Hinsdale Historical Society provides insights into the town's past and is a great place to learn about local heritage.
Can I change or cancel my Hinsdale home rental booking on Vrbo?
To find Hinsdale holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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