Hillside Vacations from $716
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Your Hillside Vacation
From its highlights to its hidden gems, this city is best experienced with a Hillside vacation package. Check out places to stay in Kingston Stockade District, which is good for families, festivals and markets. Any trip to Hillside needs a well-crafted itinerary. Fill yours with major attractions like Ulster Performing Arts Center, Hudson Valley Mall and Senate House State Historic Site. Whoever you're traveling with and whatever you want to spend, your dream Hillside vacation is only clicks away with Expedia.
The Latest Hillside Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Saratoga Casino Hotel
$716
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
9.4/10 Exceptional! (1,033 reviews)
Saratoga is always one of our favorite places, the Casino hotel is so enjoyable with an indoor pool and hot tub. Well maintained and friendly staff
Reviewed on Oct 15, 2026
The Cornell Inn, Lenox & The Berkshires
$1,072
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9.2/10 Wonderful! (1,001 reviews)
Our room was very nice with a comfortable bed, but the door to the room did not fit properly so lots of light came through the edges. Also we could hear the guests above us ( we were on first floor in carriage house) tramping around at 6:00 am. It would help to carpet the floors. The breakfast, which was much hyped, was only okay. The ingredients were nothing special, for example the bread used for toast appeared to be off the grocery store shelf.
Reviewed on Oct 14, 2026
Brook Bound Inn
$811
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9.4/10 Exceptional! (19 reviews)
Our weeklong trip meandering the roads of Vermont was made more memorable by our stay at the Brook Bound Inn! The property is gorgeous and impeccably maintained! Our room was clean and so quiet! The bed was comfortable, and the blackout window blinds allowed us to sleep a little later than normal. The bathroom was very clean with a large shower and great smelling body wash, shampoo, etc. Jake and Hope were so helpful before and during our stay. We also appreciated the robust WIFI. We didn’t try the amazing pool this time, but we will for sure on our next trip!
Reviewed on Aug 30, 2026
Hillside Hotel Deals
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
$169 nightly
$191 total
Nov 9 - Nov 10
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
"We loved the uniqueness of this very special inn. The history is amazing. Our room had been upgraded to include a bathroom, tv, etc., of course, but still felt timeless."
Reviewed on Oct 15, 2026
Courtyard by Marriott Kingston
500 Frank Sottile Blvd Kingston NY
Fully refundableReserve now, pay when you stay
$127 nightly
$142 total
Oct 25 - Oct 26
Total with taxes and fees
Holiday Inn Express Poughkeepsie by IHG
2750 South Road Poughkeepsie NY
Fully refundable
$79 nightly
$92 total
Nov 15 - Nov 16
Total with taxes and fees
8.6/10 Excellent! (1,007 reviews)
"Great!"
Reviewed on Oct 15, 2026
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.