Hillside Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to ₩234,741 when you book a flight and hotel together*

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

    Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Hillside

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

Kingston Stockade District

1 out of top 10 points of interest in this area

You'll enjoy the churches and spas in Kingston Stockade District. You might want to make time for a stop at Senate House State Historic Site or Birch Body Care.

Find hotels in Kingston Stockade District

Hillside Hotel Deals

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 ₩158,105 per night from Nov 3 to Nov 4
₩158,105
₩183,599 total
Nov 3 - Nov 4
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
We had some issues with ants in the room, around the coffee bar. We reported it and were quickly given another room. Staff was helpful and friendly.

Reviewed on Oct 24, 2025

Hampton Inn & Suites Poughkeepsie
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 ₩132,090 per night from Nov 3 to Nov 4
₩132,090
₩153,389 total
Nov 3 - Nov 4
includes taxes & fees
7.6/10 Good! (460 reviews)
x

Reviewed on Oct 24, 2025

Quality Inn Poughkeepsie
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
2702 Main St, Gardiner, NY
The price is ₩1,598,607 per night from Nov 25 to Nov 26
₩1,598,607
₩1,852,600 total
Nov 25 - Nov 26
includes taxes & fees
9.4/10 Exceptional! (54 reviews)
Where do I start…. Everything was clean and felt so luxurious. The staff was unbelievably polite, kind, and caring. The grounds are beautiful. The spa is perfect. The amenities are top tier. The food is TRULY farm to table (you can go see the farm on a 5 minute walk if you need proof). Just the perfect ...

Reviewed on Sep 16, 2025

Wildflower Farms, Auberge Collection
See all 1,438 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 vacation 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 vacation to Hillside costs.
What are the cheapest months to go to Hillside?
If you'd like to score a cheap Hillside vacation 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 travelers.
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 vacation 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 traveling on a weekday, when prices are often lower.
Is it cheaper to book a Hillside vacation as a package?
You can enjoy significant savings on your Hillside break by booking a personalized vacation 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 vacation package to Hillside?
If you've got your Hillside vacation 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 favorite 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 accommodations 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 personalized Hillside vacation package.

Discover the most popular places to visit in Hillside

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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.