Hillside Lake Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $2,033, price is now CA $1,114 per person
CA $1,114
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

Eurostars Wall Street

Eurostars Wall Street

4 out of 5
Manhattan
Price was CA $4,996, price is now CA $2,900 per person
CA $2,900
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8/10 Very good! (1,000 reviews)
Cons: Air conditioning never really worked well. Thankfully opening the window helped. It's kind of set up like an apartment so there isn't an ice machine on the floor. The TV was tiny and hard to watch. Breakfast wasn't complimentary ($19 per person). IDK for $2200 I expected a higher caliber of service and amenities. Pros: The staff was always helpful. The location is convenient especially for things downtown close the the financial district.

Reviewed on Nov 3, 2026

Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Manhattan
Price was CA $2,738, price is now CA $1,620 per person
CA $1,620
per person
Jan 10 - Jan 15
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
9.4/10 Exceptional! (555 reviews)

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $4,385, price is now CA $2,813 per person
CA $2,813
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,002 reviews)

Mandarin Oriental, New York

Mandarin Oriental, New York

5 out of 5
Manhattan
Price was CA $5,180, price is now CA $3,334 per person
CA $3,334
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (673 reviews)
Excellent stay

Reviewed on Oct 26, 2026

Ready to book your vacation to Hillside Lake?

 

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Hillside Lake Hotel Deals

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Nov 29 to Nov 30
CA $131
CA $152 total
Nov 29 - Nov 30
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

2.5 out of 5
835 Route 52 Fishkill NY
Fully refundable
The price is CA $137 per night from Nov 29 to Nov 30
CA $137
CA $158 total
Nov 29 - Nov 30
includes taxes & fees
Comfort Suites Fishkill near Interstate 84
Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A Poughkeepsie NY
Fully refundable
The price is CA $129 per night from Nov 26 to Nov 27
CA $129
CA $150 total
Nov 26 - Nov 27
includes taxes & fees
Quality Inn Poughkeepsie
See all 752 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.
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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 $1,114 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.