Hillsdale holiday lettings

We found 565 holiday rentals — enter your dates for availability

Discover a selection of 51 homes and other holiday rentals in Hillsdale that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for hanging out with the people that matter most, including air conditioning and cable TV. At the end of the day, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Hillsdale

Showing deals for:22 May - 29 May

Image gallery for Best of the Berkshires & Hudson Valley

Exterior detail
10 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)

Best of the Berkshires & Hudson Valley

Canaan

8% off
Price is £2,983
for 7 nights, 1 home
£426 per night
includes taxes & fees
Best of the Berkshires & Hudson Valley

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Take in the picturesque beauty of Hillsdale

Learn about the unique charm of Hillsdale with a stay in a holiday home rental. This city's coffee shops, skiing and horse riding attract many visitors, as does its relaxing and scenic location. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Hillsdale

Are you searching for things to do while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Hillsdale a fun place to get away to. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Catamount Ski Area (2.5 mi / 4.1 km)
  • Ski Butternut (10.5 mi / 16.9 km)
  • Hudson Chatham Winery (10.9 mi / 17.5 km)
  • Lake Taghkanic State Park (10.9 mi / 17.6 km)
  • Furnace Brook Winery at Hilltop Orchards (16.5 mi / 26.6 km)
  • Wyndhurst Golf & Club (17.4 mi / 28 km)

Exploring the natural landscape of Hillsdale

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Hillsdale is a great place to get out in nature. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Copake Lake (4.3 mi / 7 km)
  • Lake Mansfield Park (8.3 mi / 13.4 km)
  • Housatonic River Walk (8.5 mi / 13.7 km)
  • Housatonic River (8.5 mi / 13.7 km)
  • Lake Taghkanic State Park (10.9 mi / 17.6 km)
  • Berkshire Botanical Garden (12.8 mi / 20.6 km)

Travelling to and around Hillsdale

The nearest airport is in Hudson, NY (HCC-Columbia County), located 12.5 mi (20.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is 20.8 mi (33.4 km) away.

Frequently asked questions

What is the best area to stay in Hillsdale when booking a holiday rental?
When considering a holiday rental in Hillsdale, New York, the best area to stay is the charming Hillsdale village itself. This quaint community offers a delightful mix of rural charm and local amenities, making it a great base for your getaway. The village features a variety of properties, from cosy cottages to more spacious family homes, suiting different preferences and group sizes.

Staying in Hillsdale places you in close proximity to some wonderful attractions. For instance, the nearby Catamount Ski Area is a fantastic destination for winter sports enthusiasts, providing excellent skiing and snowboarding opportunities. In the warmer months, the area is equally inviting, with beautiful hiking trails and scenic spots great for picnicking and enjoying the great outdoors. Additionally, the local farmers' market is a must-visit, where you can sample fresh produce and artisanal goods, giving you a taste of the region's vibrant community spirit.
How much does it cost to rent a holiday home in Hillsdale?
Prices for holiday rentals in Hillsdale 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 Hillsdale 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 Hillsdale holiday house rentals?
You can find great discounts on house rentals in Hillsdale 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 Hillsdale ski resort rentals?
For ski resort rentals near Hillsdale, New York, travellers should focus on the nearby Catamount Ski Area, located just over the border in Massachusetts, which is easily accessible from Hillsdale. The town itself offers a range of rental options, including cosy cabins and charming chalets that provide a warm and inviting atmosphere after a day on the slopes. Many of these properties come equipped with amenities such as wood-burning fireplaces, fully stocked kitchens, and spacious living areas, great for both families and groups of friends.

In Hillsdale and the surrounding areas, visitors can find rustic lodges that often feature outdoor spaces for barbecues and relaxation, along with proximity to local attractions such as hiking trails and picturesque views of the Berkshires. Some rentals may also include access to hot tubs, which can be a delightful way to unwind after skiing.

Additionally, the nearby towns like Great Barrington and Stockbridge offer more rental choices, from modern apartments to quaint historic homes. These locations not only provide convenient access to skiing but also a vibrant local scene with shops, restaurants, and cultural attractions, making Hillsdale an excellent base for a winter getaway.
What is the most popular type of holiday rental accomodation in Hillsdale?
In Hillsdale, holiday houses are the most popular type of holiday rental, with around 123 available in the area. These homes are generally spacious and well-suited for families or larger groups, featuring multiple bedrooms, fully equipped kitchens, and often outdoor spaces like decks or gardens for relaxation. Additionally, several chalets, apartments, cabins, and cottages can be found, each offering unique charms and amenities, such as rustic decor in cabins or modern conveniences in apartments.
Are there any family house rentals in Hillsdale?
In Hillsdale, New York, families can choose from a variety of holiday rentals, with around 34 options available in the area. This charming locale is known for its picturesque landscapes and proximity to outdoor activities, making it an excellent choice for family getaways. Many properties feature spacious living areas, fully equipped kitchens great for preparing family meals, and outdoor spaces where children can enjoy themselves.

Visitors might find amenities such as Wi-Fi, laundry facilities, and even game rooms in some rentals, ensuring a comfortable stay. The area is also close to attractions like the Bash Bish Falls State Park, ideal for hiking and picnicking, and the Catamount Ski Area for winter sports enthusiasts.
Can I rent a holiday home with a pool or hot tub in Hillsdale?
In Hillsdale, New York, there are several holiday homes available for rent that feature pools and hot tubs. This charming area, located in the scenic Berkshire Mountains, offers a peaceful retreat for those looking to unwind. Many of these properties come equipped with private pools, hot tubs, and spacious outdoor areas, great for enjoying the natural beauty that surrounds the town. Travellers can also expect amenities such as fully equipped kitchens, comfortable living spaces, and, in some cases, access to hiking trails or nearby lakes.
Can I find long-stay holiday rentals in Hillsdale?
A long-stay holiday rental in Hillsdale 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 Hillsdale?
In Hillsdale, New York, there are numerous pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these holiday homes offer a variety of amenities, including fully equipped kitchens, spacious living areas, and private outdoor spaces, making them suitable for families or groups.

The rentals are often located near scenic spots, allowing for enjoyable walks and outdoor adventures with your furry companions. The surrounding area features beautiful landscapes and parks, providing ample opportunities for hiking and exploring nature.
Are there any remote work holiday rentals in Hillsdale?
In Hillsdale, New York, there are numerous remote work holiday rentals available, with around 138 options to choose from. This charming area offers a peaceful retreat for those looking to combine work and leisure. Many properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated work desks, and comfortable living spaces, allowing you to maintain productivity while enjoying the serene surroundings.

The town's picturesque landscape, with its rolling hills and proximity to the Berkshires, provides a refreshing backdrop for remote work. Additionally, local attractions such as scenic parks and quaint shops offer opportunities to unwind after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Hillsdale holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Hillsdale 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 Hillsdale?
In Hillsdale, popular rental amenities include kitchens, which allow travellers to prepare their own meals, and decks or patios that provide outdoor space for relaxation and enjoying the scenery. Many rentals also feature onsite parking for convenience, as well as fireplaces that add a cosy touch during cooler months. Additionally, some properties permit pets, making it easier for guests to bring their furry friends along for the stay.
When is the best time to visit Hillsdale for a holiday rental?
July is the most popular time to visit Hillsdale, making it an ideal choice for those seeking a vibrant holiday experience. During the peak season, which spans from June to August, visitors flock to this charming town to enjoy a variety of outdoor activities and local events. The warm summer months offer the great climate for exploring the scenic landscapes and engaging in recreational pursuits such as hiking, cycling, and enjoying the beautiful parks.

In July, you can expect pleasant temperatures averaging between 15 to 25 degrees Celsius, providing a comfortable environment for sightseeing and outdoor adventures. Whether you're strolling through the quaint streets, visiting local art galleries, or enjoying a picnic at one of the many nearby lakes, the summer atmosphere is bustling and inviting.

For those looking for a more budget-friendly option, consider visiting in October. This month showcases the stunning autumn foliage, allowing you to experience the breathtaking colours of fall while enjoying a quieter atmosphere. It's a wonderful time for leisurely walks and appreciating the natural beauty of the region.

Ultimately, your choice of when to visit Hillsdale will depend on your preferences for lively summer activities or the serene charm of autumn.
How early should I book a Hillsdale holiday rental?
Book your Hillsdale 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 Hillsdale?
In Hillsdale, New York, visitors can enjoy a variety of attractions that showcase the area's natural beauty and cultural heritage. The picturesque Hillsdale area is surrounded by rolling hills and lush landscapes, making it ideal for outdoor activities such as hiking and birdwatching. Nearby, the Catamount Ski Area offers winter sports enthusiasts a chance to ski and snowboard, while in warmer months, the same area is superb for mountain biking and scenic chairlift rides.

The town itself features charming local shops and eateries where visitors can experience the flavour of the Hudson Valley. For art lovers, the nearby Art Omi International Arts Centre presents a unique outdoor sculpture park, as well as indoor galleries showcasing contemporary art. Additionally, the nearby town of Great Barrington, just a short drive away, offers more dining and shopping options, along with cultural venues like the Mahaiwe Performing Arts Centre, which hosts various performances throughout the year.
Can I change or cancel my Hillsdale home rental booking on Vrbo?
To find Hillsdale 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 Hillsdale 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.

More holiday ideas