Hillsdale holiday lettings

We found 561 holiday rentals — enter your dates for availability

Discover a selection of 53 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:6 Mar - 13 Mar

Image gallery for Waterfront Cottage 10 Min From Great Barrington

Property grounds
10 out of 10, Exceptional, (99 reviews)
Exceptional
(99 reviews)

Waterfront Cottage 10 Min From Great Barrington

Great Barrington, MA

8% off
Price is £1,913
for 7 nights, 1 cottage
£273 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington

Find spaces that suit your style

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)
  • Lake Taghkanic State Park (10.9 mi / 17.6 km)
  • Harney and Sons Tea Tasting Room (15 mi / 24.1 km)
  • Wyndhurst Golf & Club (17.4 mi / 28 km)
  • Catskill Golf Club (18.5 mi / 29.8 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)
  • Lake Buel (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 area surrounding the charming town centre is an excellent choice. This neighbourhood offers a delightful blend of local charm and convenient access to amenities, making it ideal for visitors seeking both relaxation and exploration. You'll find a variety of properties here, from quaint cottages to spacious homes, which cater to different group sizes and preferences.

Staying near the town centre places you within easy reach of the iconic Hillsdale General Store, a superb spot to pick up local produce and artisanal goods. Additionally, the nearby Copake Lake is a lovely destination for outdoor enthusiasts, offering opportunities for kayaking, fishing, and enjoying picturesque walks along its shores. The scenic beauty of the surrounding countryside also provides a tranquil backdrop for your stay.
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 skiing in Hillsdale, New York, travellers should consider rentals in the nearby area of Catamount Ski Area, which is just a short drive away. The town of Hillsdale itself offers a selection of charming cottages and homes that provide a warm and inclusive setting. Many of these properties come equipped with essential amenities such as fully equipped kitchens, comfortable living areas, and sometimes even fireplaces, allowing guests to unwind after a day on the slopes.

Additionally, the picturesque town of Great Barrington, located a bit further north, features a range of rental options from rustic cabins to contemporary homes. These accommodations often include amenities like outdoor decks, hot tubs, and proximity to local dining and shopping options in the vibrant downtown area.
What is the most popular type of holiday rental accomodation in Hillsdale?
In Hillsdale, holiday houses are the most popular type of accommodation, with around 46 available throughout the area. These houses are often set in serene surroundings, providing a comfortable and spacious environment for families or groups. Most of these properties come equipped with fully fitted kitchens, cosy living areas, and outdoor spaces such as decks or gardens, ideal for relaxation after a day of exploring. Additionally, there are several apartments, cottages, and cabins, all offering unique charms and amenities, making Hillsdale a versatile destination for different traveller preferences.
Are there any family house rentals in Hillsdale?
In Hillsdale, New York, there are numerous family-friendly holiday rentals available, with around 44 options to choose from. This charming area is known for its picturesque landscapes and outdoor activities, making it an excellent choice for families seeking adventure and relaxation. Many of these homes feature spacious living areas, fully equipped kitchens, and outdoor spaces where children can play.
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 or hot tubs, with around 11 options to choose from. This charming town in the scenic Berkshires offers a serene escape, superb for those looking to relax in nature. Many of these properties provide amenities such as private swimming pools, inviting hot tubs, and spacious outdoor areas ideal for gatherings or quiet evenings under the stars.
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, there are several pet-friendly house rentals available, with around 35 options to choose from. Many of these properties are situated in peaceful, rural settings, offering a serene escape for travellers with pets. Guests can expect amenities such as spacious yards, which are great for pet play, fully equipped kitchens for self-catering, and comfortable living areas to relax in after a day of exploring.
Are there any remote work holiday rentals in Hillsdale?
In Hillsdale, New York, there are numerous remote work-friendly holiday rentals available, with around 51 options to choose from. This picturesque area is ideal for those looking to balance work and leisure, featuring properties equipped with essential amenities such as high-speed Wi-Fi, dedicated office spaces, desks, ergonomic chairs, and even computer monitors. Many of these rentals also offer comfortable living areas, fully equipped kitchens, and outdoor spaces, allowing for a pleasant work environment amidst the beauty of the Hudson Valley. 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 holiday rental amenities typically include a fully equipped kitchen, which features cookware, dishware, and utensils, allowing guests to prepare their own meals. Rentals also commonly include a refrigerator and stovetop for convenience. Many properties offer patios, providing outdoor space for relaxation and enjoyment of the surrounding natural beauty.
When is the best time to visit Hillsdale for a holiday rental?
July is the most popular time to visit Hillsdale, when the summer season is in full swing and travellers flock to enjoy the area's vibrant outdoor activities. Between June and August, the warm temperatures invite visitors to explore the beautiful landscapes, partake in hiking and biking, and delight in local events that showcase the charm of this picturesque town.

During July, you can expect pleasant weather, typically around 25°C during the day, superb for enjoying the nearby lakes and parks. The lively atmosphere brings together both locals and tourists, creating a wonderful sense of community and shared experience. The abundance of outdoor festivals and farmers' markets adds an extra layer of enjoyment to your stay.

If you're looking for a more budget-friendly option, October presents an excellent opportunity to experience Hillsdale's stunning autumn foliage. With fewer tourists around, you can enjoy the serene atmosphere while taking in the breathtaking views of the changing leaves. This quieter month is ideal for those seeking a peaceful retreat and an opportunity to explore the scenic beauty without the hustle and bustle of peak season.
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.
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.

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