Hillside Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to Rp16.000.000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Hillside
Holiday Inn Express Poughkeepsie by IHG
2750 South Road Poughkeepsie NY
Fully refundable
Rp1.787.094
Rp2.075.263 total
7 Sept - 8 Sept
includes taxes & fees
8.8/10 Excellent! (1,019 reviews)
"Nice stay with the family. Staff was helpful, breakast was good and free parking. Very close to Vassar College"
Reviewed on 23 Aug 2026
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
Rp3.008.865
Rp3.403.778 total
31 Aug - 1 Sept
includes taxes & fees
DoubleTree by Hilton Poughkeepsie Convention Center
40 Civic Center Plz Poughkeepsie NY
Fully refundableReserve now, pay when you stay
Rp2.161.853
Rp2.532.070 total
31 Aug - 1 Sept
includes taxes & fees
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?
- Pick your dates: The things you want to do in Hillside and your favourite season can help you decide when to travel.
- 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.
- 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.
- 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.
Things to do
Self-Guided Audio Driving Tour in Catskills Scenic Byway
Rp303.458
per traveller
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.