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
$104 nightly
The price is $122 total per night from Nov 8 to Nov 9
$122 total
Nov 8 - Nov 9
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 ...
8.4/10 Very Good! (1,000 reviews)
"A bit dated and worn. Signage could be better. But the setting is fabulous So beautiful in autumn!"

Reviewed on Nov 4, 2026

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 29 to Nov 30
$109 total
Nov 29 - Nov 30
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 ...
9/10 Wonderful! (1,159 reviews)
"Very clean, nice breakfast."

Reviewed on Nov 4, 2026

Hyatt Place Poughkeepsie / Hudson Valley
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd Suffern NY
$122 nightly
The price is $142 total per night from Dec 3 to Dec 4
$142 total
Dec 3 - Dec 4
Total with taxes and fees
Book a stay at this business-friendly hotel in Suffern. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
Crowne Plaza Suffern - Mahwah by IHG
See all 850 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.
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! (150 reviews)
"The view is unattainable from anywhere else."

Reviewed on Oct 20, 2026

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

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 ...
9/10 Wonderful! (21 reviews)
The hotel double booked rooms and upon arrival with my 15-year-old son, we were ...
"The hotel double booked rooms and upon arrival with my 15-year-old son, we were rudely turned away by the front desk person. When I questioned the woman why my room was given away, I was told they were full and I had to leave. This put me and my son in bad situation as the area's hotels were booked ..."

Reviewed on Oct 18, 2026

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
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.

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