Hillsdale vacation rentals

We found 561 vacation rentals — enter your dates for availability

Discover a selection of 52 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 13 - Mar 20

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 $331
$2,315 for 7 nights
All fees included
Waterfront Cottage 10 Min From Great Barrington

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Find out more about Hillsdale

Why visit Hillsdale

  • Outdoor Adventures: Enjoy activities like hiking, skiing, and exploring stunning national parks and serene lakes.
  • Charming Downtown: Stroll through picturesque downtown Hillsdale, perfect for summer getaways with a relaxing atmosphere.
  • Lakefront Relaxation: Unwind at the beautiful lakefront, ideal for leisure and family fun during the warmer months.
  • Diverse Accommodations: Choose from cozy cottages to spacious vacation homes that cater to every traveler's needs.
  • Welcoming Community: Experience the friendly locals who ensure a warm and inviting atmosphere throughout your stay.

Popular types of accommodation in Hillsdale

Discover the charm of Hillsdale with a variety of vacation rentals perfect for your getaway. Whether you prefer a cozy cottage, a spacious private vacation home, or a modern condo, Hillsdale has something to suit every traveler’s needs. With options like house rentals and holiday cottages, you'll find the ideal place to unwind and create lasting memories. Explore your options and enjoy a hassle-free vacation experience in this beautiful destination.

  • Houses: These spacious homes are the top choice for travelers seeking comfort and privacy, ideal for families or groups.
  • Condos: Perfect for those wanting a blend of luxury and convenience, these modern units offer great amenities and locations.
  • Cottages: These quaint and charming retreats provide a cozy atmosphere, perfect for a peaceful getaway.
  • Apartments: A practical option for visitors, offering flexibility and often located near local attractions.
  • Cabins: For a rustic experience, these cozy lodgings are nestled in nature, ideal for outdoor enthusiasts.**

Top attractions near Hillsdale

Hillsdale, New York, offers a fantastic vacation for adventure enthusiasts and sports lovers. With its stunning national parks, nature reserves, and serene lakes, the area is perfect for outdoor activities and cultural experiences. Whether you're skiing, hiking, or simply enjoying the beautiful landscapes, Hillsdale has something to offer for every traveler seeking adventure or relaxation in nature.

  • Bash Bish Falls State Park: A breathtaking destination known for its stunning waterfalls and scenic hiking trails, perfect for outdoor enthusiasts seeking adventure and natural beauty.
  • National Shrine of the Divine Mercy: A serene and culturally rich site, this shrine offers a peaceful atmosphere for reflection and spiritual connection, attracting visitors from all backgrounds.
  • Jug End State Reservation: This tranquil preserve features beautiful landscapes and wooded areas, ideal for hiking, wildlife observation, and enjoying the great outdoors.

Things to do recommended for couples

For a romantic getaway in Hillsdale, explore the slopes at Catamount Ski Area, enjoy captivating performances at Tanglewood Music Center, and savor exquisite wines at Hudson Chatham Winery. Each destination offers unique experiences perfect for couples looking to create lasting memories together.

Things to do recommended for families

Families visiting Hillsdale can enjoy a day at Lake Mansfield Park for relaxation and wellness, or explore the scenic trails at Tyringham Cobble. Stissing Lake Park also offers a great spot for recreation and family fun, making it a perfect getaway for everyone.

Things to do recommended for groups

Experience the thrill of ziplining at Catamount Aerial Adventure Park, hike the scenic Housatonic River Walk, or enjoy a show at the Mahaiwe Performing Arts Center for a taste of local culture. These activities promise fun and adventure for your group.

*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 an extended stay, it’s important to prioritize your specific needs. Here are some helpful booking tips for Vrbo 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 space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Hillsdale with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with ensuring access to age-appropriate features, 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 feels incomplete without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone, including your four-legged friend, feels comfortable and at home.
  • Planning for a long term stay visiting Hillsdale: If you're searching for vacation rentals that offer special deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can easily discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Hillsdale

Hillsdale, New York, is a charming destination perfect for outdoor enthusiasts and families alike. Enjoy the stunning scenery and relaxing atmosphere as you explore downtown Hillsdale, ideal for a summer getaway. The picturesque lakefront offers a fun place to unwind during the warmer months, while the friendly locals ensure a welcoming experience. Whether you're seeking adventure or a romantic retreat, Hillsdale has something for everyone to enjoy.

  • Great Barrington: Located 8 miles from Hillsdale, Great Barrington is a vibrant city known for its adventurous spirit and outdoor activities. Visitors flock to this area for a thrilling ski experience at the nearby ski resorts, offering diverse terrain for all skill levels. Beyond skiing, Great Barrington boasts picturesque lakes and stunning mountain views, along with access to national state parks. The combination of breathtaking landscapes and recreational opportunities makes it a perfect destination for adventure seekers.
  • Stockbridge: Situated 13 miles from Hillsdale, Stockbridge offers a unique blend of cultural richness and romantic charm. This city is renowned for its vibrant arts scene, featuring music concerts and theatrical performances throughout the year. Visitors can explore local landmarks such as serene lakes, historical monuments, and peaceful shrines. The enchanting atmosphere of Stockbridge makes it a delightful destination for those seeking entertainment and a romantic getaway, all while soaking in the area's rich history.
  • Copake: Just 5 miles from Hillsdale, Copake is an outdoor lover's paradise, perfect for adventure enthusiasts. This city is well-known for its ski fields and resorts, providing excellent opportunities for winter sports. Beyond skiing, Copake is surrounded by beautiful lakes and mountains, making it an attractive spot for hiking, fishing, and exploring the nearby national state parks. With its emphasis on outdoor activities, Copake is an ideal destination for those looking to immerse themselves in nature and enjoy exhilarating adventures.

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

Looking to save on your next vacation? Consider staying flexible with your travel dates, as this can lead to significant price differences. Furthermore, extending your stay can often unlock additional savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to narrow down your search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash from your booking. Being the planner definitely has its perks. By enrolling in our travel rewards program, OneKey, you can immediately access member discounts and earn OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo's Trip Board feature offers you a convenient way to plan your travels. You can easily create new trips, pick up right where you left off, or organize your existing plans. Any properties you've saved or booked are now neatly categorized under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/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)
  • 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 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 around the town center is an excellent choice. This charming part of Hillsdale offers a quaint, small-town atmosphere with easy access to local amenities, shops, and restaurants. Staying here puts you within a short drive of some delightful attractions, such as the beautiful Catamount Ski Area, which is superb for winter sports enthusiasts, and the stunning Olana State Historic Site, where you can explore the picturesque mansion and scenic grounds designed by renowned artist Frederic Edwin Church.

Another appealing area is the vicinity of the nearby Copake Lake, which provides a serene setting for outdoor activities like fishing, kayaking, and hiking. This area features a variety of vacation rental options, suiting different preferences and group sizes, making it a popular choice for visitors.
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 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 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 areas for renting a beach house in Hillsdale?
For renting a beach house in Hillsdale, New York, travelers should consider the nearby areas along the shores of Copake Lake and the scenic Hudson River. The Copake Lake area offers a selection of vacation rentals with picturesque views and easy access to water activities such as swimming, kayaking, and fishing. Many of these properties come equipped with amenities such as private docks, outdoor decks, and spacious yards that are superb for gatherings or relaxation.

Within a short drive, the Hudson River waterfront towns, like Hudson and Catskill, provide additional opportunities for beach house rentals. Here, travelers can find charming homes with amenities like fire pits, grills, and proximity to local parks and beaches that offer sandy spots for sunbathing or picnicking. These areas also feature vibrant local scenes with shops, restaurants, and cultural attractions, enhancing the overall experience.

Furthermore, the nearby Taconic State Park offers trails and natural beauty, making it an ideal spot for nature lovers. Rentals in the vicinity of this park often include access to hiking trails and serene landscapes, with some properties featuring outdoor patios or balconies to enjoy the peaceful surroundings.
Where are the best Hillsdale ski resort rentals?
For ski resort rentals near Hillsdale, New York, the closest ski area is Catamount Ski Area, located just a short drive away across the Massachusetts border. Travelers seeking accommodations should consider the quaint town of Hillsdale itself, which offers a variety of rental options including cozy cabins and charming cottages that reflect the area's rustic charm. Many of these properties come with essential amenities such as fully equipped kitchens, wood-burning stoves, and outdoor spaces for enjoying the stunning mountain views.

Additionally, the nearby towns of Great Barrington and Stockbridge provide a wider selection of vacation rentals, ranging from modern condos to historic homes. These rentals often feature amenities like hot tubs, fireplaces, and proximity to local shops and restaurants, making them ideal for both relaxation and convenience after a day on the slopes.

For those looking to explore the outdoors beyond skiing, the surrounding areas offer opportunities for hiking and cross-country skiing, with picturesque landscapes that showcase the beauty of the Berkshires.
What is the most popular type of vacation rental accomodation in Hillsdale?
In Hillsdale, vacation houses are the most popular type of rental, with about 46 available throughout the area. These homes often come with multiple bedrooms, fully equipped kitchens, and cozy living areas, making them ideal for families or groups looking for a spacious retreat. Additionally, there are several apartments, cottages, and cabins available, which provide a more intimate setting for travelers. Many of these rentals feature outdoor spaces, such as decks or gardens, where visitors can relax and enjoy the serene surroundings.
Are there any family house rentals in Hillsdale?
In Hillsdale, New York, there are numerous family-friendly vacation rentals available, totaling around 42 options. This charming area is surrounded by beautiful landscapes and offers a peaceful retreat for families. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can enjoy playtime. Amenities such as Wi-Fi and laundry facilities are also common, ensuring a convenient stay.

Families can explore nearby attractions, including the picturesque Catamount Ski Area for winter sports enthusiasts or the scenic hiking trails in the Taconic State Park for those who enjoy outdoor adventures. The local community offers quaint shops and farm-to-table dining experiences, providing a taste of the region's culture.
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. This charming area, located in the scenic Berkshire Mountains, offers a tranquil setting for relaxation. Many of these rentals come equipped with private outdoor pools, inviting hot tubs, and spacious patios or decks ideal for enjoying the natural surroundings.

Travelers can also expect well-appointed amenities such as fully equipped kitchens, cozy living spaces, and outdoor dining areas, making it superb for family gatherings or socializing with friends.
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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Hillsdale?
In Hillsdale, there are numerous pet-friendly house rentals available, with a total of 36 options to choose from. Visitors can expect a variety of accommodations, ranging from cozy cabins to spacious homes, often featuring amenities such as fully equipped kitchens, outdoor spaces, and comfortable living areas. Many properties may include fenced yards, making them ideal for traveling with pets.

The surrounding area offers plenty of outdoor activities for pet owners and their furry friends. Nearby parks and trails provide opportunities for hiking and exploring the natural beauty of the region, allowing pets to enjoy the great outdoors alongside their owners.
Are there any remote work vacation rentals in Hillsdale?
In Hillsdale, New York, there are plenty of remote work vacation rentals available, with around 49 options to choose from. The area is known for its serene natural surroundings and charming rural ambiance, making it an ideal setting for those looking to combine work and leisure. Many of these rentals come equipped with essential amenities for remote work, including dedicated office spaces, desks, comfortable chairs, and reliable Wi-Fi. Additionally, some properties may feature extra conveniences such as computer monitors and laptop workspaces, ensuring a productive environment.

Travelers can enjoy the picturesque views of the Berkshires and access outdoor activities like hiking and biking during their downtime. The nearby towns also offer local shops and dining options, adding to the overall experience. 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 travelers 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 include WiFi, kitchens equipped with essentials like blenders and coffee/tea makers, and outdoor patios for enjoying the surrounding scenery.
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 summer months, particularly in July, when the area comes alive with outdoor activities and vibrant local events. This peak season, spanning from June to August, offers travelers the great opportunity to enjoy warm weather, typically ranging from the mid-60s to the high 80s Fahrenheit. It's a fantastic time for hiking, biking, and exploring the scenic beauty of the Catskills, with lush landscapes and inviting trails.

In July, you can expect a lively atmosphere, as both locals and visitors partake in seasonal festivals and outdoor concerts, making it an ideal time for those seeking a blend of adventure and community spirit. The charming town of Hillsdale serves as a great base for day trips to nearby attractions, ensuring that you have plenty to do right at your doorstep.

For those looking for a more budget-friendly option, visiting in October can be a rewarding experience. This month showcases stunning fall foliage, offering a quieter atmosphere for scenic drives and leisurely hikes. The crisp air and vibrant autumn colors create a picturesque backdrop, great for photography and relaxation.

No matter when you choose to visit, Hillsdale has a unique charm that caters to outdoor enthusiasts and those who appreciate a peaceful getaway.
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.
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 offerings. The nearby Catamount Ski Area is popular for winter sports enthusiasts, offering skiing and snowboarding opportunities in the colder months. In the summer, the area transforms into a hub for hiking and mountain biking, with trails that provide stunning views of the surrounding landscape.

For those interested in arts and culture, the town has a charming local scene, with galleries showcasing works from regional artists. The close proximity to the Hudson River also allows for outdoor activities such as fishing, kayaking, and scenic boat rides.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, 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 organizing 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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