Hillside Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Hillside

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

2.5 out of 5
3423 US Highway 9W Highland NY
Fully refundableReserve now, pay when you stay
The price is 2.210.869 ₫ per night from 1 Jul to 2 Jul
2.210.869 ₫
2.476.205 ₫ total
1 Jul - 2 Jul
includes taxes & fees
7.8/10 Good! (1,002 reviews)
"Needed a clean no-frills place to stay during a road trip. Free breakfast, nice staff, clean roadside hotel. Would stay again."

Reviewed on 22 Jun 2026

SureStay Plus Hotel by Best Western Highland Poughkeepsie
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is 3.285.893 ₫ per night from 8 Jul to 9 Jul
3.285.893 ₫
3.848.601 ₫ total
8 Jul - 9 Jul
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
"I arrived and was informed that there was no air conditioning or hot water at the hotel. They said they had reached out to other hotels to accommodate their guests. They moved me to a new hotel where I had to book a new room and pay for it out of pocket. They said I would be refunded but then refused ..."

Reviewed on 22 Jun 2026

DoubleTree by Hilton Poughkeepsie Convention Center
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212 Saugerties NY
Fully refundableReserve now, pay when you stay
The price is 4.395.941 ₫ per night from 9 Jul to 10 Jul
4.395.941 ₫
5.955.317 ₫ total
9 Jul - 10 Jul
includes taxes & fees
9/10 Wonderful! (516 reviews)
"Nice stay with family"

Reviewed on 21 Jun 2026

AutoCamp Catskills
See all 1,422 properties in Hillside
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.

Frequently asked questions

How much does a Hillside holiday package cost?
You'll find cheap prices on Expedia for your Hillside break. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your holiday to Hillside costs.
What are the cheapest months to go to Hillside?
If you'd like to score a cheap Hillside holiday package, consider planning a trip in January, February and March. You'll usually find lower prices on hotels and flights during these quieter months — ideal for budget-conscious travellers.
How many days is enough for Hillside?
With a well-planned schedule, you can easily tick off the top Hillside sights in a handful of days. But if you'd like to discover hidden spots or go on day trips, think about booking your Hillside holiday for longer.
How to find the best Hillside package deals?
Bagging a cheap Hillside package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, add some filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Hillside package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Hillside holiday as a package?
You can enjoy significant savings on your Hillside break by booking a personalised holiday package. Check the "Package" heading, then enter your destination and travel dates to view the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Hillside?
If you've got your Hillside holiday dates finalized, book as early as you can to bag some terrific deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Hillside?

  1. Pick your dates: The things you want to do in Hillside and your favourite season can help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to flights and experiences. Your accommodation will probably be the biggest expense during your trip to Hillside.
  3. Decide your trip length: Think about how long you'd like to spend discovering Hillside. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalised Hillside holiday package.

Popular places to visit

Ashokan Rail Trail- Woodstock Dike Trailhead

You can take time to visit Ashokan Rail Trail- Woodstock Dike Trailhead during your travels to Kingston. Discover the area's mountain views or seek out its ski slopes.

Ashokan Rail Trail- Woodstock Dike Trailhead

Kingston Rondout Visitor Center

Kingston Rondout Visitor Center is just one of the places to see in Kingston, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the area's entertainment venues.

Kingston Rondout Visitor Center

Hudson River Maritime Museum

You can study the exhibits at Hudson River Maritime Museum, a museum with a story of its own, during your trip to Kingston. Experience the area's entertainment venues and festivals.

Hudson River Maritime Museum