Hillside Lake Vacation Packages

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  • Better together

    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.
Eurostars Wall Street

Eurostars Wall Street

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $1,825, price is now CA $1,102 per person
CA $1,102
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8/10 Very good! (1,000 reviews)
The best part of this hotel is the proximity and the size of the room. Hotel staff really hands-off, no amenities. Hotel very out dated and kind of dingy looking.

Reviewed on Nov 6, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $2,502, price is now CA $1,381 per person
CA $1,381
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

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 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
9.4/10 Exceptional! (555 reviews)

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was CA $2,262, price is now CA $1,386 per person
CA $1,386
per person
Jan 13 - Jan 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (1,000 reviews)
Clean and comfortable

Reviewed on Nov 2, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,809, price is now CA $3,009 per person
CA $3,009
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

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 $138 per night from Nov 29 to Nov 30
CA $138
CA $160 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 $130 per night from Nov 29 to Nov 30
CA $130
CA $151 total
Nov 29 - Nov 30
includes taxes & fees
Quality Inn Poughkeepsie
See all 758 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
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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 $1,102 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.