Discover Your Ideal Highland, New York, USA Vacation Rentals Near Olana for a Memorable Getaway
Discover Your Perfect Olana Vacation Homes
Best Vacation Homes in Olana
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Why Choose Rent By Owner for your Olana Vacation Rental Homes?
What makes our Vacation Rentals special?
Best Times to Visit Olana
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here can enhance your experience, so consider planning your stay during the season when the region’s natural beauty and local events align for a memorable getaway.
Peak Season Highlights
Spring (April to June)
During this time, the area's landscape flourishes with vibrant blooms, making it an ideal season for sightseeing and outdoor activities. The pleasant weather typically encourages longer daytime exploration, perfect for enjoying your stay.
Fall (September to November)
This season offers stunning fall foliage, creating an inviting atmosphere that enhances your experience of the region's natural beauty. It is a popular period for travelers seeking picturesque scenery and outdoor excursions.
Off-Season Highlights
Winter (December to February)
The winter months bring a quieter ambiance, allowing you to enjoy the region’s serene beauty with fewer crowds. This is a great time for cozy stays and exploring indoor attractions nearby.
Late Summer (August)
Following the summer rush, late August provides a more relaxed atmosphere with warm weather still lingering. It’s an excellent choice if you prefer avoiding peak tourist periods while still enjoying comfortable temperatures.
Weekly Weather Forecast for Olana
How to Book Your Olana Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Olana
Common Vacation Rentals Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a spacious outdoor patio or deck perfect for relaxing and dining al fresco while taking in scenic views of the surrounding landscape.
- Take advantage of well-maintained gardens or landscaped yards that add to the charm and tranquility of your stay here.
- Make use of outdoor grilling facilities, ideal for hosting barbecues during warm summer evenings in the area.
- Relax in a private or shared outdoor pool, providing a refreshing escape after exploring the region's attractions.
- Benefit from access to hiking trails or nature walks directly from the property, allowing you to immerse yourself in the area's natural beauty.
- Utilize outdoor fire pits or fireplaces, perfect for cozy gatherings and enjoying starry nights under this destination’s clear sky.
- Take part in outdoor recreational activities such as bocce, horseshoes, or other lawn games available at select properties here.
Top Attractions Around Olana
What attractions are nearby?
Within this scenic region, you can enjoy a variety of outdoor activities and cultural experiences just a short drive from your vacation rental in Highland, offering an enriching stay amidst the natural beauty and local attractions nearby.

Family Activities
- Hudson River Expeditions: Experience family-friendly guided boat tours along the scenic Hudson River, offering a unique way to explore the area's natural beauty.
- Walkway Over the Hudson State Historic Park: Enjoy an easy stroll across this iconic bridge with spectacular views, perfect for a leisurely family outing in the region.
- Frog Hill Farm: Discover farm activities and animal encounters that make for an engaging outdoor experience suitable for children and adults alike.
- Local Nature Trails: Immerse yourself in the countryside by exploring well-maintained trails that provide scenic routes for hiking and picnicking with your loved ones.
Adult Activities
- Hudson River Cruises: Embark on a scenic cruise along the Hudson River to enjoy breathtaking views and learn about the area's rich history.
- Dining Experiences: Indulge in locally sourced cuisine at renowned restaurants that showcase the region's culinary talent and fresh ingredients.
- Historic Tours: Explore the area's fascinating history by visiting preserved landmarks and participating in guided tours that highlight its cultural significance.
- Art Galleries and Studios: Discover local art at galleries and studios nestled within the region, offering unique pieces and creative inspiration.
Olana Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Visit Ahead: Booking your vacation rentals early ensures you secure the best accommodations near popular attractions in the area.
- Explore Local Flavors: Take advantage of regional cuisine and dining options to fully immerse yourself in the local culture during your stay.
- Schedule Outdoor Activities: Leverage the region’s scenic landscapes for outdoor adventures that make your trip memorable and engaging.
- Utilize Nearby Amenities: Choose a rental property close to essential services and attractions for convenient access throughout your visit.
Transportation Options
- Personal Vehicles: Driving your own car offers the flexibility to explore this destination and its surrounding scenic areas at your own pace.
- Public Transit (Bus): Local bus services connect you to key spots in the region, making it a convenient option for exploring without the hassle of parking.
- Taxi and Rideshare Services: Taxis and rideshare options provide quick and reliable transportation around here, ideal for short trips within the area.
- Bike Rentals: Biking is an eco-friendly way to discover the region’s charming neighborhoods and natural beauty while enjoying the fresh air.
Local Customs Options
- Local Art Appreciation: You will find that art plays a vital role here, with residents often celebrating their rich cultural history through community events and exhibitions that highlight the region’s artistic traditions.
- Farm-to-Table Dining: Many local eateries emphasize fresh, locally sourced ingredients, reflecting the area's commitment to sustainable practices and regional culinary heritage.
- Historic Preservation: Respect for the area's history is evident in its well-preserved architecture and landmarks, encouraging visitors to appreciate the region's historical roots.
- Community Festivals: Seasonal festivals and celebrations are commonplace here, providing an authentic glimpse into the local customs and fostering a sense of togetherness among residents and visitors alike.
Frequently Asked Questions About Olana?
1. What are the top vacation rentals in Olana?
There are a lot of options in Olana. If you plan on staying in the Olana area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Olana:
- NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool
- Cozy & Charming Farm House just 85 miles north of NYC
- Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
- Charming Brick House -Hudson Valley
- for the creative spirit, swimming dock on pond, horses to pet, Fire pit
- Best of both worlds! Amazing views plus an easy walk into town!
- Splendid Isolation: Private Luxury. Breathtaking Modern Villa On Hudson Bluffs.
- Sweet spot studio on village outskirts
- The Bear Den at 'Blue Heron Watch' Nature Getaway
- Nestled in Lush Landscape Near New Paltz Village
2. How many Rentbyowner vacation rentals are available in Olana?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 235 in the Olana area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Olana.
3. What is the cancellation policy for booking a vacation rental in Highland, New York?
4. How do I find the most suitable vacation rental in Olana for my stay?
5. Are there any specific check-in or check-out procedures I should be aware of in Highland, NY?
6. What safety and cleanliness measures are implemented in vacation rentals in the region?
7. How can I confirm my reservation and what steps are involved after booking a vacation rental here?
Best Vacation Homes in Olana
- Air Conditioner
- Parking
- View
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- View
- Air Conditioner
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- TV
- Air Conditioner
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- Pet Friendly
- Air Conditioner
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- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- TV
- Security/Safety
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV