Discover Your Perfect Town of Highlands Vacation Homes

Best Vacation Homes in Town of Highlands

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Town of Highlands Luxury Rentals

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Find More Town of Highlands Villas, Resorts, & Rentals on BedroomVillas

Town of Highlands Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your Town of Highlands Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Town of Highlands

When should you plan your Vacation Rentals stay?

Choosing the right time to visit this charming region ensures you can enjoy its natural beauty and tranquil atmosphere at their best when booking your perfect vacation rental here.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, the area experiences peak visitation as travelers seek outdoor activities and scenic relaxation, making it an ideal time for booking vacation rentals that offer a peaceful retreat.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

This destination becomes especially popular in the fall when vibrant foliage draws visitors looking to enjoy the region’s natural beauty, perfect for those seeking cozy vacation rentals with picturesque surroundings.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

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Winter (December to February)

During the winter months, fewer tourists visit, offering a quieter experience for those interested in peaceful vacation rentals away from busy crowds while enjoying the serene winter landscape.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F
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Spring (March to May)

In early spring, visitation slows down before the full bloom, providing an excellent opportunity to book vacation rentals at more affordable rates while experiencing the area's budding natural beauty.

Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Town of Highlands

How to Book Your Town of Highlands Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Town of Highlands

More Top-Rated Vacation Rentals in Town of Highlands Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

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 outdoor grilling with a fully equipped barbecue area for family cookouts.
  • Relax on spacious decks or patios that offer scenic views of the surrounding landscape.
  • Make the most of private or shared outdoor pools to stay cool during warmer months.
  • Take advantage of well-maintained hiking trails nearby to explore the area's natural beauty.
  • Spend time around cozy fire pits, perfect for evening gatherings and stargazing.
  • Utilize outdoor sports facilities such as tennis courts or volleyball areas if available.
  • Use designated parking spaces close to your rental for easy access to outdoor activities.

Top Attractions Around Town of Highlands

What attractions are nearby?

In this charming destination, you can enjoy outdoor activities such as hiking, fishing, and exploring scenic parks, all just a short distance from your vacation rental in the region.

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Family Activities

  • Garrison Art Center: Engage in creative family activities at this renowned art center, offering workshops and exhibitions suitable for all ages, nestled within the scenic surroundings of the area.
  • Bear Mountain State Park: Explore the great outdoors with family-friendly hiking trails, picnicking spots, and stunning mountain views perfect for a day trip here.
  • Hudson Highlands Cruises: Discover the region from a new perspective by taking a boat tour along the Hudson River, offering memorable sightseeing experiences for families.
  • Highlands Fall Farm: Enjoy a day of farm fun, including seasonal activities such as berry picking and petting zoos, ideal for creating lasting family memories in the area.
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Adult Activities

  • Hiking and Nature Walks: Explore the scenic trails and lush landscapes that surround this destination, offering a peaceful retreat into nature's tranquility.
  • Visit Local Art Galleries: Discover the vibrant art scene in the area by browsing galleries showcasing regional artists and handcrafted works.
  • Fishing in Nearby Waters: Enjoy leisurely fishing excursions on nearby lakes or rivers, perfect for unwinding and connecting with nature.
  • Dining at Farm-to-Table Restaurants: Savor fresh, locally sourced cuisine at restaurants that celebrate the region’s farm-fresh ingredients and culinary traditions.

Other Places to Stay in Town of Highlands, NY

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Michie Stadium
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West Point
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Fort Montgomery
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West Point Golf Course
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More Places to Stay Near Town of Highlands

Town of Highlands Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities Early: Take advantage of the area’s natural beauty by scheduling outdoor adventures and scenic excursions ahead of time to maximize your experience here.
  • Explore Local Dining Options: Immerse yourself in the regional cuisine by trying nearby restaurants, which can add an authentic touch to your stay in this destination.
  • Utilize Nearby Amenities: Make the most of local conveniences and services available close to your vacation rentals to ensure a comfortable and hassle-free visit.
  • Schedule Downtime for Relaxation: Set aside time to unwind at your rental property, enjoying the peaceful surroundings that define this region’s charm and tranquility.

Transportation Options

  • Car Rentals: Renting a car provides you with the flexibility to explore the scenic area around your vacation rental in the region at your own pace.
  • Public Transit: The local bus services offer an affordable and convenient way to navigate here without the need for personal transportation.
  • Taxis and Rideshare Services: Easily book a taxi or rideshare to arrive comfortably at your vacation rental or explore nearby attractions in the destination.
  • Bicycle Rentals: Cycling is a great eco-friendly option, allowing you to enjoy the natural beauty that surrounds this area firsthand.

Local Customs Options

  • Local Dress Code: When visiting here, you'll notice that dressing comfortably and casually is customary, reflecting the region's laid-back and outdoor-oriented lifestyle.
  • Community Events: Participating in seasonal festivals and outdoor gatherings is a cherished tradition, offering an authentic glimpse into local culture and hospitality.
  • Respect for Nature: As nature enthusiasts frequent this area, maintaining environmental respect by following trail guidelines and waste disposal practices is highly valued.
  • Historical Appreciation: Appreciating the region's history through visits to local landmarks and observing preservation efforts demonstrates the community's pride and identity.

Frequently Asked Questions About Town of Highlands?

1. What are the top vacation rentals in Town of Highlands?

There are a lot of options in Town of Highlands. If you plan on staying in the Town of Highlands area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Town of Highlands:

2. Which vacation homes in Town of Highlands are best for families?

If you are looking for a family-friendly vacation home in Town of Highlands, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Town of Highlands:

3. How many Rentbyowner vacation rentals are available in Town of Highlands?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 57 in the Town of Highlands 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 Town of Highlands. 

4. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the property owner, so it’s best to review the specific listing details or contact the host directly for their cancellation terms and any associated fees.

5. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning fees, service charges, or occupancy taxes are often outlined in the listing details. It’s recommended to read the full description or reach out to the property owner to confirm all costs before booking.

6. How do I ensure my reservation is secure and confirmed?

Reservations are secured through the booking platform's secure system once you complete the payment process. For confirmation or any special requests, contacting the property owner directly can provide added reassurance.

7. Can I modify or cancel my reservation if my plans change?

Modification and cancellation options depend on the individual property’s policies. Check the specific listing for details or contact the owner to discuss potential changes and any applicable fees.

8. What amenities are typically included with vacation rentals in this region?

Amenities vary by property but generally include essentials like Wi-Fi, heating, and kitchen facilities. To ensure your needs are met, review the listing details carefully or contact the owner for specific amenity availability.