Hillside Lake Vacations from $211

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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.
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
Save 100% on your flight
Price was $405, price is now $211 per person
$211
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9/10 Wonderful! (1,825 reviews)
I had a great experience there and a very comfortable stay

Reviewed on Nov 25, 2025

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was $631, price is now $297 per person
$297
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
8.6/10 Excellent! (2,613 reviews)
The location was ideal for our stay. The restaurant food was amazing.

Reviewed on Nov 22, 2025

Windrose On Hudson

Windrose On Hudson

3 out of 5
Price was $911, price is now $440 per person
$440
per person
Feb 5 - Feb 11
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
7.8/10 Good! (80 reviews)
I wish there was a coffee maker in the room, also the TV was very small and angled away from the bed. It was super quiet, which was great, and very clean and warm.

Reviewed on Nov 16, 2025

Hilton Garden Inn Westchester Dobbs Ferry, NY

Hilton Garden Inn Westchester Dobbs Ferry, NY

3 out of 5
Price was $452, price is now $223 per person
$223
per person
Jan 30 - Feb 3
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
8.4/10 Very Good! (1,001 reviews)
Beautiful place to be

Reviewed on Nov 20, 2025

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was $1,269, price is now $664 per person
$664
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9/10 Wonderful! (1,002 reviews)
helpful staff, nice rooms, location

Reviewed on Nov 24, 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

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
$84 nightly
The price is $98 total per night from Dec 16 to Dec 17
$98 total
Dec 16 - Dec 17
Total with taxes and fees
7.6/10 Good! (488 reviews)
Best stay!

Reviewed on Nov 20, 2025

Quality Inn Poughkeepsie
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
$99 nightly
The price is $115 total per night from Dec 5 to Dec 6
$115 total
Dec 5 - Dec 6
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
Spotless room

Reviewed on Nov 24, 2025

Hampton Inn & Suites Poughkeepsie
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
915 Union Ave New Windsor NY
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $118 total per night from Dec 1 to Dec 2
$118 total
Dec 1 - Dec 2
Total with taxes and fees
8.2/10 Very Good! (1,007 reviews)
Very friendly front desk staff!

Reviewed on Nov 23, 2025

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
See all 745 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.

Find the Best Hillside Lake Vacation Packages

Hillside Lake Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
1,100
Top Sights
Canopus Beach, Beekman Golf Course and East Fishkill Community Library

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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 $211 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.