Preston Hollow vacation rentals

We found 482 vacation rentals — enter your dates for availability

Discover a selection of 5 homes and other vacation rentals in Preston Hollow that are perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the best amenities for hanging out with the people that matter most, which might include WiFi and a pool. No matter what you're looking for, you'll find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Preston Hollow

Showing deals for:Feb 13 - Feb 20

Image gallery for Beautiful Historic Farmhouse with Gorgeous Views

Aerial view
10 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)

Beautiful Historic Farmhouse with Gorgeous Views

Middleburgh, NY

10% off
Price is CA $365
CA $3,311 total
includes taxes & fees
Beautiful Historic Farmhouse with Gorgeous Views

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Find out more about Preston Hollow

Why visit Preston Hollow

  1. Outdoor Adventure: Enjoy skiing and exploring scenic trails, perfect for outdoor enthusiasts.
  2. Charming Village Atmosphere: Experience the friendly, family-oriented vibe of Preston Hollow Village.
  3. Beautiful Parks: Discover stunning national and state parks, along with lovely arboretums.
  4. Unique Camping Experiences: Camp amidst nature's beauty at local campgrounds.
  5. Diverse Accommodations: Choose from cozy cabins, private homes, and charming cottages for your stay.

Popular types of accommodation in Preston Hollow

Planning a getaway to Preston Hollow? You're in for a treat! Explore a variety of popular vacation rentals, including private homes, charming cabins, and cozy cottages. Whether you're looking for apartments near Preston Hollow Village or active vacation rentals, we’ve got you covered. Enjoy the comforts of home while discovering all that this beautiful area has to offer. Your perfect stay awaits!

  • Houses: The top choice for visitors, offering spacious and comfortable accommodations perfect for families or groups in Preston Hollow.
  • Cabins: A popular option among nature lovers, these rustic retreats provide a cozy atmosphere amidst the beautiful surroundings.
  • Cottages: Charming and quaint, cottages in Preston Hollow offer a delightful getaway for couples or small families.
  • Apartments: Ideal for those seeking a more urban experience, these rentals provide convenience and amenities in a home-like setting.
  • Chalets: These alpine-inspired lodgings offer a unique stay, blending comfort with stunning views of the landscape.**

Top attractions in Preston Hollow

Preston Hollow, New York, is perfect for adventure seekers and outdoor enthusiasts, offering opportunities for skiing and exploration. Visitors can discover local attractions such as national and state parks, modern civic buildings, and beautiful arboretums. Whether you're after outdoor activities, cultural experiences, or breathtaking scenery, Preston Hollow has something to offer for every traveller, making it an ideal destination for your vacation.

  1. Tenmile Creek: Located 11.3km from Preston Hollow, this scenic river offers a tranquil outdoor experience, perfect for fishing, kayaking, or simply enjoying the natural beauty surrounding it.
  2. Mine Kill State Park: Situated 19.3km away, this national park features stunning landscapes and thrilling adventure opportunities, including hiking trails and waterfalls, ideal for outdoor enthusiasts.
  3. Mountain Top Arboretum: About 25.7km from Preston Hollow, this family-friendly arboretum showcases a diverse collection of plants and beautiful walking paths, perfect for a leisurely stroll in nature.

Things to do recommended for couples

For a romantic getaway in Preston Hollow, indulge in skiing at Windham Mountain Resort, explore the charming Windham Vineyards and Winery, or take an adventurous ride on the 20th Century Ski Lift. Each offers unique outdoor experiences perfect for couples seeking adventure and romance.

Things to do recommended for families

Families exploring Preston Hollow can have a splashing good time at Zoom Flume, a thrilling waterpark located 9.7km away. With exciting slides and wave pools, it offers endless adventure and entertainment for all ages, making it a perfect spot for a memorable family day out.

Things to do recommended for groups

Enjoy a round of golf at Windham Country Club or Rainbow Golf Club for some outdoor fun. For a scenic adventure, hike the Vroman's Nose Trailhead, where you'll experience breathtaking views and the beauty of nature just a short drive from Preston Hollow.

What do I need to keep in mind when booking a vacation in Preston Hollow

If you’re planning a trip with friends, family, pets, or seeking extended accommodations, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Preston Hollow with a group: Think about how many bedrooms you require, as well as amenities like a full kitchen or outdoor space for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Preston Hollow with young kids: Traveling with young children can present its own set of challenges. It's essential to prioritize their comfort and safety, as well as access to 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 Preston Hollow: For many, a family getaway isn’t truly fulfilled without their furry companion by their side. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Preston Hollow: If you're seeking vacation rentals with special offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Preston Hollow

Preston Hollow, nestled in New York, offers a delightful blend of adventure and relaxation. From the charming Preston Hollow Village to nearby neighborhoods, visitors can enjoy a warm, family-friendly atmosphere. Outdoor enthusiasts can explore scenic trails and ski spots, while those seeking romance will find serene settings perfect for a getaway. Don't miss the local campgrounds for a unique camping experience amidst nature's beauty.

  • Windham: Located 14.5km from Preston Hollow, Windham is renowned for its outdoor adventures, particularly skiing. This vibrant city offers access to a variety of ski fields and resorts, making it a haven for winter sports enthusiasts. In addition to skiing, visitors can explore the picturesque landscapes featuring mountains, serene lakes, and stunning waterfalls. Windham’s charming village atmosphere beckons tourists to enjoy local shops and eateries, providing a perfect blend of adventure and relaxation.
  • Hunter: Situated 24.1km from Preston Hollow, Hunter is another exceptional destination for outdoor and ski lovers. Encircled by breathtaking mountains and valleys, this city offers a wealth of activities from skiing to hiking. The local ski resorts are popular spots for both novice and experienced skiers. Additionally, the area boasts beautiful natural attractions, including tranquil lakes and spectacular waterfalls, ensuring a memorable experience for nature enthusiasts and adventure seekers alike.
  • Durham: Just 6.4km from Preston Hollow, Durham is a charming city that caters to those seeking adventure and outdoor experiences. Known for its ski opportunities, Durham also features an exciting theme park that adds a touch of fun for families. The surrounding landscape includes beautiful mountains and lakes, ideal for hiking, fishing, or simply soaking in the natural beauty. With its close proximity to Preston Hollow, Durham is an excellent choice for a quick getaway filled with adventure.

Best time to go to Preston Hollow

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

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January21.9°F (-5.6°C)Light RainMostly CloudyAverageSlightly High
February24.1°F (-4.4°C)Light RainMostly CloudyAverageSlightly High
March31.6°F (-0.2°C)Light RainMostly CloudyModerately LowSlightly Low
April43.3°F (6.3°C)Light RainMostly CloudyModerately LowSlightly Low
May55.6°F (13.1°C)Light RainMostly SunnyAverageAverage
June63.0°F (17.2°C)Light RainMostly SunnyAverageAverage
July68.7°F (20.4°C)Light RainMostly SunnyModerately HighAverage
August66.7°F (19.3°C)Light RainMostly SunnyModerately HighAverage
September59.9°F (15.5°C)Light RainMostly SunnyAverageSlightly Low
October48.9°F (9.4°C)Light RainMostly SunnyModerately HighAverage
November36.7°F (2.6°C)Light RainMostly SunnyModerately LowAverage
December28.8°F (-1.8°C)Light RainMostly CloudyAverageSlightly High

Booking with Vrbo is simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Plus, opting for a longer stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental. We're here to help you find the best options for your trip!

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient platform to plan new adventures, pick up right where you left off, or manage your travel itinerary with ease. You can easily access your previously saved and booked properties, which are now categorized under Potential, Upcoming, or Current Trips. To make the most of Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Choose a vacation rental for your Preston Hollow getaway

Learn about the unique charm of Preston Hollow with a stay in a private vacation home. There's no shortage of things to see and do in the area.If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Preston Hollow

Are you looking for attractions to see while you're in town? Venture out of your cozy vacation rental and check out everything that makes Preston Hollow a one-of-a-kind vacation spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Hunter Mountain (16.2 mi / 26 km)
  • Zoom Flume (5.8 mi / 9.3 km)
  • Windham Vineyards and Winery (7.9 mi / 12.7 km)
  • Windham Country Club (9.1 mi / 14.7 km)
  • Windham Mountain Resort (10.1 mi / 16.2 km)
  • Mountain Trails Cross Country Ski and Snowshoe Center (17.2 mi / 27.6 km)

Exploring the natural features in Preston Hollow

Whether you're looking for fun outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Preston Hollow. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Irish Cultural Center (8.7 mi / 14.1 km)
  • Vroman's Nose Trailhead (12.8 mi / 20.6 km)
  • Mountain Top Arboretum (15.5 mi / 25 km)
  • Thompsons Lake State Park Beach (17.8 mi / 28.6 km)
  • Thacher State Park (18.7 mi / 30.2 km)
  • East Branch Delaware River (29.2 mi / 47 km)

Traveling to and around Preston Hollow

The nearest airport is in Hudson, NY (HCC-Columbia County), located 28.1 mi (45.3 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Albany Intl. Airport (ALB), which is 30.2 mi (48.7 km) away.

Frequently asked questions

What is the best area to stay in Preston Hollow when booking a vacation rental?
When considering a vacation rental in Preston Hollow, New York, the best area to stay in would be the charming neighbourhood surrounding the heart of the community. This area offers a delightful blend of scenic beauty and local charm, making it a superb base for your getaway. With a selection of approximately 20 to 30 rental properties available, visitors can find a range of options to suit various preferences and budgets.

One of the top attractions nearby is the picturesque Catskill Park, which is renowned for its stunning landscapes and outdoor recreational opportunities. Whether you're keen on hiking, fishing, or simply enjoying a leisurely stroll, the park provides an idyllic backdrop for nature lovers. Additionally, the historic Preston Hollow Community Centre often hosts events and activities that can give you a taste of local culture and community spirit.
How much does it cost to rent a vacation home in Preston Hollow?
Prices for vacation rentals in Preston Hollow 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 Preston Hollow to more spacious homes.
Are there any discounts for Preston Hollow vacation house rentals?
You can find great discounts on house rentals in Preston Hollow 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.
What is the most popular type of vacation rental accomodation in Preston Hollow?
In Preston Hollow, vacation houses are the most popular type of rental accommodation, with several available throughout the area. These properties often feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them superb for families or larger groups. Many vacation houses also come with outdoor spaces, such as gardens or patios, ideal for enjoying the tranquil surroundings. Additionally, there are several cabins, mobile homes, and cottages for travellers seeking a more unique or rustic experience.
Are there any family house rentals in Preston Hollow?
In Preston Hollow, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. This affluent neighbourhood features spacious properties that often include multiple bedrooms, ample living areas, and fully equipped kitchens, superb for preparing family meals. Many homes also boast outdoor spaces, such as gardens or patios, where kids can play and families can relax.
Can I find long-stay vacation rentals in Preston Hollow?
A long-stay vacation rental in Preston Hollow 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 Preston Hollow?
In Preston Hollow, there are several pet-friendly house rentals available, making it a suitable destination for travellers accompanied by their furry friends. The area offers a range of vacation homes that typically feature amenities such as spacious backyards, fully equipped kitchens, and comfortable living areas, allowing both pets and their owners to relax and enjoy their stay.
Are there any remote work vacation rentals in Preston Hollow?
In Preston Hollow, there are several remote work vacation rentals available, making it an excellent choice for those looking to blend work and leisure. These properties typically feature essential amenities such as Wi-Fi, desk chairs, and dedicated workspaces, ensuring a comfortable environment for productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Preston Hollow vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Preston Hollow 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 Preston Hollow?
In Preston Hollow, popular rental amenities include fully equipped kitchens, allowing guests to prepare meals with ease. Many properties also feature outdoor spaces such as patios or decks, which provide a lovely setting for dining al fresco or simply relaxing in the fresh air. Additionally, dining tables are commonly found in these rentals, making them ideal for families or groups to gather for meals together.
How early should I book a Preston Hollow vacation rental?
Book your Preston Hollow 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 Preston Hollow home rental booking on Vrbo?
To find Preston Hollow 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 Preston Hollow 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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