Hillsdale vacation rentals

We found 566 vacation rentals — enter your dates for availability

Discover a selection of 51 homes and other vacation rentals in Hillsdale that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation homes have the amenities you expect for your stay, which might include parking and a fireplace. No matter what you're looking for, you're sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Hillsdale

Showing deals for:Mar 27 - Apr 3

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

New Marlborough

10% off
Price is CA $375
CA $3,372 total
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington

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Find out more about Hillsdale

Why visit Hillsdale

  • Outdoor Activities: Enjoy skiing, hiking, and exploring the stunning natural landscapes of Hillsdale and its surrounding national parks.
  • Charming Local Culture: Experience the warmth of friendly locals and the romantic vibe in the picturesque small hamlets.
  • Hillsdale Farmers Market: Immerse yourself in local offerings at this vibrant market, showcasing fresh produce and artisanal goods.
  • Cozy Accommodations: Choose from charming private homes, cozy condos, and delightful cottages, many featuring inviting outdoor spaces.
  • Serene Lakes: Relax by the tranquil lakes, perfect for quiet moments in nature or family-friendly activities.

Popular types of accommodation in Hillsdale

If you're wondering what types of vacation rentals await you in Hillsdale, look no further. Our most popular options include charming houses, cozy condos, and delightful cottages. Many of these accommodations feature inviting back decks, private patios, and seasonal pools for your enjoyment. Plus, dog runs are available for your furry companions, ensuring everyone has a fantastic stay. Discover the perfect getaway in Hillsdale today.

  • Houses: The top choice for visitors to Hillsdale, these homes offer ample space and comfort, perfect for families or groups seeking a home-like atmosphere.
  • Condos: A popular option, condos provide modern amenities and often come with added conveniences like pools or fitness centres.
  • Cottages: These charming retreats provide a quaint and cozy experience, ideal for those wanting a peaceful getaway.
  • Apartments: A practical choice, apartments offer a homey feel with the benefit of self-catering facilities.
  • Cabins: For a rustic experience, cabins are a favourite among nature enthusiasts looking for a serene escape.**

Top attractions near Hillsdale

Hillsdale, New York, is a fantastic destination for skiing, adventure, and sports vacations, offering a range of attractions like national parks, nature reserves, and serene lakes. Whether you're seeking outdoor activities, cultural experiences, or thrilling adventures, Hillsdale has it all. Don't miss the local highlights such as the charming city of Hillsdale and the vibrant Hillsdale Farmers Market, perfect for immersing yourself in the area's unique offerings.

  • Bash Bish Falls State Park: Experience the natural beauty of this national park, featuring breathtaking waterfalls and scenic hiking trails. Perfect for outdoor enthusiasts seeking adventure and tranquility, it’s a must-visit for nature lovers.
  • National Shrine of the Divine Mercy: This serene shrine offers a unique cultural experience, inviting visitors to reflect and appreciate its beautiful architecture and spiritual ambiance, along with the stunning gardens.
  • Norman Rockwell Museum: Celebrate American art and culture at this museum, showcasing Norman Rockwell's iconic works. It’s a delightful destination for art lovers and those interested in storytelling through visuals.

Things to do recommended for couples

Hillsdale offers a delightful romantic getaway. Enjoy skiing at Catamount Ski Area, just 3.2km away, or indulge in a wine tasting at Hudson Chatham Winery, 17.7km from town. For a night of entertainment, don’t miss the Tanglewood Music Center, located 25.7km from Hillsdale.

Things to do recommended for families

Your family will love exploring Lake Mansfield Park, only 12.9km from Hillsdale, perfect for relaxation and wellness. Tyringham Cobble and Stissing Lake Park, both 25.7km away, also offer serene environments for outdoor fun and family bonding amidst nature.

Things to do recommended for groups

Groups visiting Hillsdale can experience the thrill of the Catamount Aerial Adventure Park with its zipline ropes course, enjoy a captivating show at the Mahaiwe Performing Arts Center, and play a round of golf at the scenic Greenock Country Club nearby.

*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 Hillsdale

When traveling with a group, family, pets, or planning for extended stays, it’s important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Hillsdale with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Hillsdale with young kids: Traveling with young kids can be quite the adventure. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Hillsdale: For many families, a vacation just isn’t the same without their furry companion. If you can relate, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Hillsdale: 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 conveniently discover and save on monthly rentals. Don't forget to include options like parking, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Hillsdale

Hillsdale, New York, is a hidden gem in the Hudson Valley, perfect for a relaxing adventure. Explore charming small hamlets amidst hilly landscapes, where you can ski or immerse yourself in the local scenery. Experience the warmth of friendly locals and the romantic vibe of this picturesque region. Whether you're seeking family-friendly activities or quiet moments in nature, Hillsdale offers a delightful escape for every traveller.

  • Great Barrington: Located 12.9km from Hillsdale, Great Barrington is a vibrant city that beckons adventure seekers and outdoor enthusiasts. Known for its excellent skiing facilities, visitors can enjoy activities at local ski resorts and fields, making it a popular winter destination. Beyond winter sports, the area boasts beautiful lakes and scenic mountains, perfect for hiking and exploring during the warmer months. Great Barrington's charming downtown features local shops, cafes, and a lively arts scene, providing a well-rounded experience for travelers.
  • Stockbridge: Situated 20.9km from Hillsdale, Stockbridge offers a rich cultural experience in a picturesque setting. This charming city is famous for its artistic heritage, with numerous galleries and theaters showcasing local talent. Visitors can enjoy music concerts and theatrical performances, making it an ideal spot for a romantic getaway or cultural exploration. The area is also home to lovely lakes and notable landmarks, including monuments and shrines, inviting travelers to immerse themselves in the history and beauty of this iconic New England town.
  • Copake: Just 8.0km from Hillsdale, Copake presents a wonderful destination for those seeking outdoor adventures. Known for its skiing opportunities, the city features ski fields and resorts that attract winter sports enthusiasts. During the summer months, visitors can explore the surrounding national state parks and enjoy hiking or picnicking by the scenic lakes and mountains. With its laid-back atmosphere and connection to nature, Copake is perfect for those looking to unwind and embrace the great outdoors.

Best time to go to Hillsdale

If you're planning a trip to Hillsdale, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in January to February and July, while off-peak times, like March, October and December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.0°F (-3.9°C)Light RainMostly CloudySlightly HighAverage
February26.6°F (-3.0°C)Light RainMostly CloudySlightly HighSlightly Low
March34.5°F (1.4°C)Light RainMostly CloudySlightly LowSlightly Low
April46.2°F (7.9°C)Light RainMostly CloudyAverageSlightly Low
May57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
June65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
July72.0°F (22.2°C)Light RainMostly SunnySlightly HighAverage
August70.0°F (21.1°C)Light RainMostly SunnyAverageSlightly High
September62.8°F (17.1°C)Light RainMostly SunnyAverageAverage
October51.6°F (10.9°C)Light RainMostly SunnySlightly LowAverage
November39.4°F (4.1°C)Light RainMostly SunnyAverageSlightly High
December31.3°F (-0.4°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your next getaway? Being open to adjusting your travel dates can really help, as prices tend to vary. Additionally, if you opt for a longer stay, you often unlock significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the ideal spot for your adventure.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a helpful platform for you to plan your journeys, seamlessly pick up from where you last left off, or review and arrange your travel plans. You can easily find your saved or booked properties organized into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Take in the picturesque beauty of Hillsdale

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

Activities and attractions in Hillsdale

Do you want to find things to do while you're in the area? Venture out of your cozy vacation rental and experience everything that Hillsdale has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Wyndhurst Golf & Club (17.4 mi / 28 km)
  • Catskill Golf Club (18.5 mi / 29.8 km)
  • Kennedy Park (18.8 mi / 30.2 km)

Exploring the natural landscape of Hillsdale

Whether you're an adventurous traveler or just want to take in the scenery, Hillsdale is a great place to get outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • 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)

Traveling to and around Hillsdale

The nearest airport is in Hudson, NY (HCC-Columbia County), located 12.5 mi (20.1 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to 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 vacation rental?
When considering a vacation rental in Hillsdale, New York, the area of Hillsdale Village is an excellent choice. This quaint village is not only picturesque but also conveniently located near some of the region's top attractions. Staying here offers easy access to the scenic landscapes of the Berkshires, making it superb for those who enjoy outdoor activities such as hiking and exploring nature.

One of the highlights of Hillsdale Village is its proximity to the Catamount Ski Area, which is ideal for winter sports enthusiasts. In warmer months, visitors can enjoy the beauty of the nearby Bash Bish Falls State Park, a stunning natural waterfall that is superb for a day of hiking and picnicking. The village itself has a charming atmosphere with local shops and eateries that provide a taste of the community's character.
How much does it cost to rent a vacation home in Hillsdale?
Prices for vacation 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 travelling 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.
Are there any discounts for Hillsdale vacation 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 in Hillsdale, New York, travellers should consider the nearby Catamount Ski Area, which is just a short drive away. The surrounding area offers a variety of rental options, particularly in the charming town of Hillsdale itself and nearby towns like Great Barrington and Copake.

In Hillsdale, visitors can find quaint cottages and rustic lodges that provide a cozy atmosphere, ideal for groups or families. Many of these properties come equipped with essential amenities such as fully stocked kitchens, comfortable living areas with wood-burning stoves or fireplaces, and outdoor spaces for enjoying the natural surroundings.

Great Barrington, a bit further south, offers additional choices, including modern apartments and traditional New England homes. Many of these rentals feature amenities like hot tubs for après-ski relaxation, spacious decks, and proximity to local dining and shopping options.
What is the most popular type of vacation rental accomodation in Hillsdale?
In Hillsdale, vacation houses are the most popular type of rental, with approximately 46 available throughout the area. Many of these houses offer spacious living areas, fully equipped kitchens, and outdoor spaces such as patios or decks, superb for enjoying the tranquil surroundings. Additionally, there are several apartments, cottages, and cabins, each providing a great experience. Cottages often feature rustic charm and a cosy atmosphere, while cabins may include amenities like fireplaces and proximity to nature trails.
Are there any family house rentals in Hillsdale?
In Hillsdale, New York, there are a variety of family-friendly house rentals available, with around 44 options to choose from. This charming area boasts spacious homes, superb for families looking to enjoy a getaway surrounded by nature. Many properties feature amenities such as fully equipped kitchens, large living rooms for family gatherings, and outdoor spaces where children can play or adults can relax.
Can I rent a vacation home with a pool or hot tub in Hillsdale?
In Hillsdale, New York, there are several vacation homes available for rent that feature pools and hot tubs, with around 11 options to choose from. This picturesque town, located in the scenic Berkshire Mountains, offers a tranquil retreat for those looking to relax. Many of the rentals come equipped with private pools, hot tubs, and spacious outdoor areas, ideal for enjoying the beautiful surroundings during warmer months.
Can I find long-stay vacation rentals in Hillsdale?
A long-stay vacation 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 pet-friendly house rentals available, offering a variety of options for travellers with pets. Many of these rentals feature amenities such as spacious gardens or yards, ideal for pets to roam freely, and fully equipped kitchens for convenient self-catering. The local area is known for its picturesque landscapes and outdoor activities, making it a great choice for those looking to enjoy nature with their furry companions.
Are there any remote work vacation rentals in Hillsdale?
In Hillsdale, New York, there are plenty of remote work-friendly vacation rentals available, with around 51 options to choose from. This picturesque area is ideal for those looking to combine work and leisure amidst beautiful natural surroundings. Many properties come equipped with dedicated office spaces, desks, and comfortable chairs, ensuring a productive environment. High-speed Wi-Fi is commonly provided, along with amenities such as laptop workspaces and computer monitors, making it easy to set up an efficient work area. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Hillsdale vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation 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 vacation rental?
The best time to visit Hillsdale for a vacation rental is during the peak season from June to August, particularly in July when the area comes alive with activity. This summer period is ideal for those seeking outdoor adventures, as the warm weather invites exploration of the beautiful landscapes, hiking trails, and nearby lakes. Visitors can enjoy a range of activities, including kayaking, swimming, and attending local festivals that showcase the vibrant community spirit.

In July, temperatures typically hover in the high teens to low twenties Celsius, providing a comfortable climate for outdoor pursuits and leisurely sightseeing. This month is especially popular, so you can expect a lively atmosphere with other travellers enjoying the local offerings, from quaint shops to farm-to-table dining experiences.

For those looking for a more budget-friendly option, October presents a wonderful opportunity to experience the stunning autumn foliage that New York is famous for. This month allows for a quieter exploration of the scenic countryside, with fewer crowds and the chance to witness the vibrant colours of fall.
How early should I book a Hillsdale vacation rental?
Book your Hillsdale 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.
Can I change or cancel my Hillsdale home rental booking on Vrbo?
To find Hillsdale 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 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 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.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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