Highland Mills, NY

Travel Guide

A calm lake at sunset with trees and grass along the shore.
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
$97 nightly
The price is $114 total per night from Nov 10 to Nov 11
$114 total
Nov 10 - Nov 11
Total with taxes and fees
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Overlook Lodge at Bear Mountain
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
$94 nightly
The price is $109 total per night from Nov 15 to Nov 16
$109 total
Nov 15 - Nov 16
Total with taxes and fees
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hyatt Place Poughkeepsie / Hudson Valley
Tappan Zee Hotel

Tappan Zee Hotel

2 out of 5
110 N Route 303 West Nyack NY
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $95 total per night from Oct 16 to Oct 17
$95 total
Oct 16 - Oct 17
Total with taxes and fees
Stay at this motel in West Nyack. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Lucky ...
6.6/10 (762 reviews)
"It was fine. Cheaper than all the other hotels nearby."

Reviewed on Oct 12, 2026

Tappan Zee Hotel
See all 857 properties in Highland Mills
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen

Fishkill NY
Stay at this apartment in Fishkill. Enjoy free WiFi, cable/satellite TV service, and air conditioning. Popular attractions Van Wyck Homestead Museum and Fishkill ...
8.4/10 Very Good! (26 reviews)
The reviews were not reflective of what my sister and I found. The beds were co ...
"The reviews were not reflective of what my sister and I found. The beds were comfortable and clean. The bathroom was a nice size. The kitchenette was nice to have although you should bring paper plates and plastic utensils as well as a coffee maker and cups and glasses. Ice, if you will need it. ..."

Reviewed on Oct 12, 2026

2 Queen Beds | Non-Smoking, Kitchen
1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen

Fishkill NY
Stay at this apartment in Fishkill. Enjoy free WiFi, cable/satellite TV service, and air conditioning. Popular attractions Van Wyck Homestead Museum and Fishkill ...
7.8/10 Good! (26 reviews)
"The property was clean and pet friendly. However, the small extended stay room with a kitchen had no glasses or bowls or flat ware. You can't expect any additional accomodations beyond the room."

Reviewed on Oct 12, 2026

1 Queen Bed | Non-Smoking, Kitchen
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery NY
Stay at this cottage in Fort Montgomery. Enjoy free WiFi, a garden, and patios. Popular attractions Bear Mountain State Park and Manitoga The Russel Wright Design ...
9.8/10 Exceptional! (148 reviews)
"Lovely basement one bedroom on top of a mountain with a fabulous view of Bear Mt Bridge and surroundings. Comfortable outside patio with chairs, lounges and night lights. Interesting mix of antiques with a South Asia flair and USA college pennants! 10 minute drive from West Point. Clean and ..."

Reviewed on Sep 26, 2026

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
See all properties in Highland Mills
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Highland Mills attractions

Palaia Vineyards Winery

You can enjoy a tasting or tour at Palaia Vineyards Winery during your travels to Woodbury. Discover the mountain views and shops in this family-friendly area.
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Frequently asked questions

When is the best time to visit Highland Mills?
The best time to visit Highland Mills is from May through September, when the weather is generally pleasant for exploring. For travelers seeking fewer crowds and better value, the cooler months of December through March are a good option, offering a quieter experience and often winter scenery.
What is Highland Mills known for?
Highland Mills is known for Palaia Vineyards Winery. Travelers can visit this local winery to experience the region's winemaking. It offers a relaxed setting for enjoying local wines.
What is a good itinerary length for Highland Mills?
A good itinerary length for Highland Mills is one to two days to fully experience Palaia Vineyards Winery. This allows time for tastings and enjoying the vineyard's atmosphere. An extended stay of three days provides a more leisurely pace, with opportunities to savor diverse local dining, including European, Italian, and Asian cuisine.
What are the top things to do in and around Highland Mills?
In Highland Mills, visit Palaia Vineyards Winery, a local landmark where you can enjoy wine tastings.
Can I book a refundable hotel in Highland Mills?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Highland Mills by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Highland Mills with Expedia?
Expedia makes it easier to plan your Highland Mills trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Highland Mills?
The best choice depends on your travel style. Hotels in Highland Mills can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Highland Mills trip on Expedia?
Once you've booked your Highland Mills trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Highland Mills trip?
Expedia offers customer support before, during, and after your Highland Mills trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Highland Mills?
If it's your first trip to Highland Mills, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Highland Mills hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Highland Mills hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Highland Mills

A calm lake at sunset with trees and grass along the shore.

New Windsor

A suspension bridge over a river with surrounding hills and dense forest.

Central Valley

A river winding through a densely forested valley with hills in the background.

Harriman

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Cornwall

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