Hillside Lake Vacations from $380

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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!

The Latest Hillside Lake vacation packages

Price found within the past 48 hours. Click for updated prices.
Windrose On Hudson

Windrose On Hudson

3 out of 5
Price was $761, price is now $380 per person
$380
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
8.4/10 Very Good! (9 reviews)
Only one night so did not use the amenities. The refrigerator in the room died in the night so lost my leftovers. The room was clean and the staff was helpful. The shower function was strange. I would stay there again.

Reviewed on Aug 12, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was $2,127, price is now $1,105 per person
$1,105
per person
Oct 30 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.8/10 Exceptional! (1,293 reviews)
Great people, great place, rooms are spot on and Rooftop is worth every penny

Reviewed on Aug 26, 2025

Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
Price was $1,335, price is now $702 per person
$702
per person
Oct 30 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.6/10 Good! (870 reviews)
BEST – The hotel is very close to the Flatiron, with several subway lines reachable within a 5-minute walk. It’s clean, and the room is fine if you just need a place to shower and sleep. The front desk is available 24/7. WORST – Unfortunately, our room (707) was right next to a technical room, so we could hear mechanical noises day and night. We also asked for the TV to be fixed, but it was never taken care of.

Reviewed on Aug 26, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $2,792, price is now $1,488 per person
$1,488
per person
Oct 4 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug 21, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
Price was $753, price is now $404 per person
$404
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
The hotel itself was nice. There is truly nothing but senior citizens that stay here. We walked in and thought it was a nursing home. I’m not joking there must have been at least 60 70year olds when we walked in. They just take over the entire hotel. Again, the hotel itself is nice, but I think we would stay somewhere else knowing what we know now especially with two teenage boys with us.

Reviewed on Aug 28, 2025

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Discover the most popular places to visit in Hillside Lake

Poughkeepsie Galleria

You can do some window-shopping at Poughkeepsie Galleria during your trip to Wappingers Falls. Stroll along the riverfront or attend a sporting event in the area.

Poughkeepsie Galleria

Bowdoin Park

Explore the great outdoors at Bowdoin Park, a lovely green space in Wappingers Falls. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.

Bowdoin Park

Fun Central

Enjoy a stop at Fun Central, an entertaining place to visit in Wappingers Falls. Amble around the area's riverfront or attend a sporting event.

Fun Central

Hillside Lake Hotel Deals

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
$93 nightly
The price is $109 total per night from Sep 2 to Sep 3
$109 total
Sep 2 - Sep 3
Total with taxes and fees
7.2/10 Good! (523 reviews)
"Our stay was good properly, was formerly or another property. It was a sheraton before, and I guess this new hotel took over for what it was worth. The hotel was nice clean comfortable. We need some upkeeping. For some remodeling, but the service was great.Bid was comfortable had no problem"

Reviewed on Aug 26, 2025

The Crossroads Hotel, Newburgh
Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

2.5 out of 5
849 Route 52, Fishkill, NY
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $113 total per night from Sep 14 to Sep 15
$113 total
Sep 14 - Sep 15
Total with taxes and fees
8.8/10 Excellent! (1,014 reviews)
Nice place to stop off I84
"Check in woman was super friendly. Room was spacious, clean and comfortable. Traveling with my daughter and this was about our halfway point. Its right off of I84, next to a diner that appeared to be well known due to how busy it looked, and a gas station down the street. Hotel was quiet and couldnt ..."

Reviewed on Aug 25, 2025

Quality Inn & Suites Fishkill South near I-84
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
$99 nightly
The price is $115 total per night from Sep 8 to Sep 9
$115 total
Sep 8 - Sep 9
Total with taxes and fees
7.6/10 Good! (403 reviews)
"Overall good stay"

Reviewed on Aug 24, 2025

Quality Inn Poughkeepsie
See all 748 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 grab a vacation package to this popular destination from $380 on Expedia. But how much your vacation to Hillside Lake costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Hillside Lake?
You can usually find lower prices and greater availability in January, June and December. Explore our cheap Hillside Lake vacation packages and you could score some great off-season discounts.
How many days is enough for Hillside Lake?
The ideal duration of your Hillside Lake vacation depends on what you'd like to do. Generally, a few days to a week will give you plenty of time to hit all the major sights and discover some hidden spots along the way.
How to find the best Hillside Lake package deals?
Begin your search for a Hillside Lake package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Hillside Lake package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Hillside Lake adventure off to a flying start.
Is it cheaper to book a Hillside Lake vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still get the freedom to create a personalized Hillside Lake vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Hillside Lake?
If you're planning a spur-of-the-moment Hillside Lake adventure, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land terrific deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Hillside Lake vacation packages?
Your Hillside Lake getaway should be a relaxing escape from your daily routine, not a reason for money-related stress. So to give you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.