Photo by Janine Edmondson

Hinsdale holiday lettings

We found 696 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:24 Apr - 1 May

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 £1,874
for 7 nights, 1 cottage
£268 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington

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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)
  • 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)
  • Furnace Brook Winery at Hilltop Orchards (13.6 mi / 21.9 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 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:

  • Wood's Pond (8.8 mi / 14.2 km)
  • 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)
  • Chesterfield Gorge (12.8 mi / 20.6 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 a holiday rental in Hinsdale, Massachusetts, the most appealing area to stay in is near the charming downtown district. This area offers a delightful mix of local shops and eateries, making it convenient for visitors to explore the community. You'll find a variety of properties available, ranging from quaint cottages to more spacious homes, ensuring that there's something to suit different preferences and group sizes.
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, travellers should explore the nearby areas of Stockbridge and Great Barrington, situated along the picturesque shores of Lake Mahkeenac. In Stockbridge, holiday rentals often feature charming lakefront properties with amenities such as private docks, outdoor patios, and spacious gardens. Many houses come equipped with fully stocked kitchens and comfortable living areas, superb for families or groups seeking a relaxing retreat by the water.

Great Barrington also offers a variety of rental options, including cozy cottages and larger homes that provide easy access to the lake. These properties frequently boast amenities like fire pits for evening gatherings, and some have kayaks or canoes available for guests, ideal for enjoying the tranquil waters. The town is also known for its vibrant arts scene and local eateries, offering plenty of options for dining and entertainment.
Where are the best Hinsdale ski resort rentals?
For those seeking ski resort rentals near Hinsdale, Massachusetts, the closest options can be found at nearby ski areas such as Jiminy Peak. Located just a short drive away in Hancock, this resort offers a variety of accommodations, including lodges and condos that cater to different group sizes. Many of these properties come equipped with modern amenities such as full kitchens, living areas with fireplaces, and access to communal hot tubs, providing a comfortable retreat after a day on the slopes.

In Hinsdale itself, travellers may find charming cabins and rustic lodges that offer a more secluded experience, often set amidst beautiful wooded landscapes. These rentals typically feature cosy interiors, outdoor fire pits, and sometimes even access to private trails for cross-country skiing or snowshoeing. The area's serene environment makes it an excellent choice for those looking to escape the hustle and bustle.
What is the most popular type of holiday rental accomodation in Hinsdale?
In Hinsdale, holiday houses are the most common type of rental, with several available throughout the area. These properties typically offer spacious living arrangements, including multiple bedrooms, fully equipped kitchens, and often outdoor decks or gardens, providing a great setting for family gatherings or group retreats. Additionally, there are also several cottages and cabins that cater to those seeking a more rustic experience; these usually feature charming decor, wood-burning stoves, and proximity to nature. For those looking for a more compact option, several apartments are available, which generally include essential amenities like kitchen facilities and comfortable living spaces.
Are there any family house rentals in Hinsdale?
In Hinsdale, Massachusetts, there are several family-friendly house rentals available, making it a wonderful choice for those travelling with children. The town's charming atmosphere is complemented by its proximity to natural attractions, including the scenic hiking trails of the Berkshires and the tranquil waters of nearby lakes.

Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can enjoy themselves. Some properties may even offer amenities such as game rooms, fire pits, and private gardens, superb for family gatherings and relaxation after a day of exploring.
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, offering a range of amenities to ensure a comfortable stay. Many of these properties feature spacious living areas, fully equipped kitchens, and outdoor spaces such as decks or gardens, ideal for both relaxation and entertaining.

The area is known for its scenic beauty, with proximity to the picturesque beaches of the Berkshires and numerous hiking trails, making it a great destination for outdoor enthusiasts. Nearby, the stunning Lake Ashmere offers opportunities for swimming, fishing, and kayaking, which can be enjoyed with your furry companions.
Are there any remote work holiday rentals in Hinsdale?
In Hinsdale, Massachusetts, there are several remote work holiday rentals available, with around 15 options to choose from. This scenic area offers a tranquil environment conducive to productivity, with many properties featuring dedicated office spaces, desks, and ergonomic chairs. Travellers can expect amenities such as high-speed Wi-Fi and computer monitors, making it easy to set up a comfortable workspace while enjoying the beauty of the Berkshires. 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 include fully equipped kitchens, which often feature dishwashers and microwaves, allowing guests to prepare meals during their stay. Many of these rentals come with cookware, dishware, and utensils, ensuring that travellers have everything they need for a comfortable and convenient experience.
When is the best time to visit Hinsdale for a holiday rental?
The peak season for visiting Hinsdale, Massachusetts, is from May to July, with July being the most popular month. This time of year draws outdoor enthusiasts eager to explore the beautiful landscapes and partake in various activities, such as hiking, kayaking, and fishing in the serene waters of nearby lakes. The pleasant summer temperatures typically range in the high teens to low twenties Celsius, creating ideal conditions for outdoor adventures and sightseeing.

In July, Hinsdale buzzes with life, offering a vibrant atmosphere filled with fellow travellers and a range of events that celebrate the local culture. Whether you're wandering through the charming streets, enjoying a picnic in the park, or soaking up the sun by the water, the summer months provide ample opportunities for unforgettable experiences.

For those looking for a more budget-friendly option, consider a visit in October. This month offers the chance to witness the stunning autumn foliage as the leaves transform into a spectacular array of colours. October's cooler temperatures, generally in the low teens Celsius, create a lovely backdrop for leisurely hikes and scenic drives, allowing for a quieter exploration of the area's natural 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.
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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