Hillside Holidays

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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

Hampton Inn & Suites Poughkeepsie
Hampton Inn & Suites Poughkeepsie
2.5 out of 5
2361 South Rd, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is S$173 per night from 24 Jun to 25 Jun
S$173
24 Jun - 25 Jun
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Clean, spacious rooms and friendly staff. The included breakfast was very good and amenities include a pool, gym and laundry room. Would highly recommend Hampton Inn Poughkeepsie."

Reviewed on 5 Jun, 2025

Hampton Inn & Suites Poughkeepsie
Beekman Arms Hotel
Beekman Arms Hotel
3.5 out of 5
6387 MILL ST, Rhinebeck, NY
The price is S$231 per night from 11 Jun to 12 Jun
S$231
11 Jun - 12 Jun
includes taxes & fees
8.2/10 Very Good! (710 reviews)
"Very convenient place to stay, the grounds are beautiful, didn't receive clear directions to find our room, but enjoyed being there."

Reviewed on 9 Jun, 2025

Beekman Arms Hotel
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
3 out of 5
25 OLD VINEYARD PLACE, Hyde Park, NY
Fully refundableReserve now, pay when you stay
The price is S$234 per night from 7 Jul to 8 Jul
S$234
7 Jul - 8 Jul
includes taxes & fees
9.6/10 Exceptional! (335 reviews)
"Great"

Reviewed on 4 Jun, 2025

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
See all 1,432 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.

Things to do

Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

S$84
per adult
100% of travellers recommend
Llama/Alpaca Hike and Farm Tour
See all activities in Kingston

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.