Hillside Holidays

Book a Hotel + Flight or Car together to unlock savings

Where to stay in Hillside

Find the best Hillside areas and neighborhoods for the activities you enjoy most. Learn more about Hillside
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Roundout

2 out of top 10 points of interest in this area

While visiting Roundout, you might make a stop by sights like Hudson River Maritime Museum and Trolley Museum of New York.

Find hotels in Roundout

Top hotels in Hillside

Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is 2.713.372 ₫ per night from 9 Sept to 10 Sept
2.713.372 ₫
3.150.904 ₫ total
9 Sept - 10 Sept
includes taxes & fees
7.6/10 Good! (392 reviews)
"Nice."

Reviewed on 15 Aug 2025

Quality Inn Poughkeepsie
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
2702 Main St, Gardiner, NY
The price is 26.596.459 ₫ per night from 1 Sept to 2 Sept
26.596.459 ₫
30.922.986 ₫ total
1 Sept - 2 Sept
includes taxes & fees
9.4/10 Exceptional! (52 reviews)
"Such a dreamy escape. The staff is excellent, friendly, and always ready to help. The rooms are serene and comfortable. Amazing spa and spa staff. Restaurant is also top-notch"

Reviewed on 15 May 2025

Wildflower Farms, Auberge Resorts Collection
Americas Best Value Inn New Paltz

Americas Best Value Inn New Paltz

2 out of 5
7 Terwilliger Ln, New Paltz, NY
Fully refundableReserve now, pay when you stay
The price is 2.489.797 ₫ per night from 28 Aug to 29 Aug
2.489.797 ₫
2.788.573 ₫ total
28 Aug - 29 Aug
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"The hotel staff was very nice and my stay was pleasant. I didn't encounter any issues and was very happy with the cleanliness of the rooms. Check-in and check-out were easy. I got a lot of communication from the hotel beforehand. The free breakfast was basic but adequate. The coffee from the machine ..."

Reviewed on 15 Aug 2025

Americas Best Value Inn New Paltz
See all 1,436 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