Hillside Lake Vacation Packages

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Your Hillside Lake Vacation

Book a Hillside Lake vacation package that has everything you need and no unnecessary extras. Great for families, history and culture, consider staying in the neighborhood of Poughkeepsie Waterfront. When it's time to head out and see the sights, be sure to put East Fishkill Community Library and Beekman Golf Course on the to-do list for your trip to Hillside Lake. Stop dreaming and start doing. Browse the multitude of options on Expedia today and put your Hillside Lake vacation plans into gear!

Top Hillside Lake Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Save 100% on your flight
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,429 reviews)
Great location! Friendly staff and very clean.

Reviewed on Jul. 6, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.4/10 Very Good! (532 reviews)
Right on the water. Private beach with chair and umbrellas.they will serve you right on the beach bye getting you food and drinks also has a outdoor swimming pool..nice staff..nothing special about the continental breakfast..bagels, fruit, small croissants, small danish and some hard boiled eggs..coffee and oj..i was pleased with my stay. King deluxe room..small table with chairs on the shared deck..could sit outside til about 2pm and the sun starts to beat on you but no biggy..was very humid out when my wife and i was there..a/ c really could not cool the room as much as we would have liked. Nothing wrong with the a/c it just because the sun beating on the hotel all day..luckily i brought a couple of small usb fans to help keep cool at night while we slept did the trick..overall i enjoy my stay and you could not ask for anything more when it comes to the scenery..

Reviewed on Jul. 10, 2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.8/10 Good! (1,475 reviews)
Can’t wait to come back!!!

Reviewed on Jul. 15, 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
Staff are fantastic!

Reviewed on Jul. 7, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
great location! great view! great bar!

Reviewed on Jul. 14, 2025

Ready to book your vacation to Hillside Lake?

 

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Hillside Lake Hotel Deals

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 CA $139 per night from Jul 30 to Jul 31
CA $139
CA $161 total
Jul 30 - Jul 31
includes taxes & fees
7.8/10 Good! (371 reviews)
"Not enough food on breakfast after 8:30am"

Reviewed on Jul. 13, 2025

Quality Inn Poughkeepsie
Wingate by Wyndham Fishkill

Wingate by Wyndham Fishkill

3 out of 5
20 Schuyler Blvd, Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from Jul 27 to Jul 28
CA $143
CA $161 total
Jul 27 - Jul 28
includes taxes & fees
7.4/10 Good! (444 reviews)
July Weekend
"It was a nice place to stay for a short time. The employees are very nice."

Reviewed on Jul. 14, 2025

Wingate by Wyndham Fishkill
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road, Poughkeepsie, NY
Fully refundable
The price is CA $131 per night from Aug 4 to Aug 5
CA $131
CA $152 total
Aug 4 - Aug 5
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"We found this wonderful location to be just perfect!! Our check-in was a breeze, and the clerk was extremely accommodating. After a quiet night's rest we had the hotel's great hot breakfast. Plenty of free parking, right off a very convenient commercial corridor; I highly recommend this Holiday Inn, ..."

Reviewed on Jul. 13, 2025

Holiday Inn Express Poughkeepsie by IHG
See all 764 properties in Hillside Lake
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

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Frequently asked questions

How much does a Hillside Lake vacation package cost?
You can pick up a vacation package to this top destination from CA $767 on Expedia. However, how much your vacation to Hillside Lake costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Hillside Lake?
If you're looking to book a cheap Hillside Lake vacation package, consider travelling in January, February and March. You'll typically find lower rates on flights and accommodations during these quieter months --- perfect for a budget-friendly getaway.
How many days is enough for Hillside Lake?
Usually, a handful of days is enough to visit the top sights during your Hillside Lake vacation. However, if you prefer to have time to rest or go on day tours, consider extending your trip.
How to find the best Hillside Lake package deals?
Begin your search for a Hillside Lake package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Hillside Lake package deal straight away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Hillside Lake escape off to a flying start.
Is it cheaper to book a Hillside Lake vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking hotels and flights separately. Better still, you can customize your Hillside Lake trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Hillside Lake?
Score fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Hillside Lake getaway.
How to plan a trip to Hillside Lake?

  1. Choose your dates: What you plan to do in Hillside Lake and your preferred season will help you decide when to go.
  2. Calculate your budget: Make sure you have enough money to pay for everything from food and transportation to flights and experiences. Your hotel will likely be the largest expense during your trip to Hillside Lake.
  3. Work out your trip length: Consider how much time you want to spend discovering Hillside Lake. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Hillside Lake vacation package that brings all your bookings together.

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