Castle Point Vacation Packages

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Your Castle Point Vacation

Say farewell to the hassle of planning and hello to a Castle Point vacation package. With the finer details organized before you leave, you can focus on discovering this city, starting with Poughkeepsie Waterfront, which is great for families, history and culture. Any trip to Castle Point needs a well-crafted itinerary. Fill yours with leading attractions like Poughkeepsie Galleria, Bowdoin Park and Dutchess Stadium. No matter your travel plans or the size of your budget, putting together a tailored Castle Point vacation is a cinch with Expedia.

Top Castle Point Vacation Deals

Price found within the past 48 hours. Click for updated prices.
San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Manhattan
Price was CA $1,639, price is now CA $1,030 per person
CA $1,030
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (1,820 reviews)

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was CA $1,874, price is now CA $1,055 per person
CA $1,055
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.6/10 Excellent! (2,500 reviews)
I will definitely will stayed at this hotel again

Reviewed on Jul 24, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $2,798, price is now CA $1,701 per person
CA $1,701
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (3,226 reviews)
Our stay at the Rui was excellent. It was so clean, well maintained and the staff were so friendly. The breakfast was excellent as well. I would definately recommend staying there, because the location was perfect.

Reviewed on Jul 25, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $2,481, price is now CA $1,543 per person
CA $1,543
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (3,768 reviews)
Alarm in middle of night was scary could not understand what person was telling us over and over 3 alarms

Reviewed on Jul 24, 2026

The Fifty Sonesta Hotel New York

The Fifty Sonesta Hotel New York

4 out of 5
Manhattan
Price was CA $1,814, price is now CA $1,153 per person
CA $1,153
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,528 reviews)
Great location with subway access close by. 20 minute walk to central park. Hotel itself is a bit outdated but no complaints. Check in was smooth and staff were always polite and welcoming.

Reviewed on Jul 24, 2026

Ready to book your vacation to Castle Point?

 

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Castle Point Hotel Deals

Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from Aug 16 to Aug 17
CA $126
CA $146 total
Aug 16 - Aug 17
includes taxes & fees
8.4/10 Very good! (186 reviews)
"Great place to stay"

Reviewed on Jul 24, 2026

Spark by Hilton Fishkill
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 $164 per night from Aug 9 to Aug 10
CA $164
CA $190 total
Aug 9 - Aug 10
includes taxes & fees
9/10 Wonderful! (1,015 reviews)
"Beautiful spacious suite ,great breakfast, Gym good machines"

Reviewed on Jul 24, 2026

Hyatt Place Poughkeepsie / Hudson Valley
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Jul 30 to Jul 31
CA $207
CA $255 total
Jul 30 - Jul 31
includes taxes & fees
8.4/10 Very good! (1,021 reviews)
"The scenery was magical!!"

Reviewed on Jul 24, 2026

Overlook Lodge at Bear Mountain
See all 769 properties in Castle Point
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
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Castle Point vacation package cost?
You'll find cheap prices from CA $1,030 on Expedia for your Castle Point break. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Castle Point costs.
What are the cheapest months to go to Castle Point?
If you're hoping to snag a cheap Castle Point vacation package, consider travelling in January, February and March. You'll generally find lower prices on airfares and hotels during these months — perfect for budget-conscious travellers.
How many days is enough for Castle Point?
Typically, a handful of days is enough to visit the main attractions during your Castle Point vacation. But if you want to have some time to chill out or go on day trips, consider extending your trip.
How to find the best Castle Point package deals?
Begin your search for a Castle Point package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" 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 irresistible savings. If you don't find the perfect Castle Point package deal right away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Castle Point adventure underway.
Is it cheaper to book a Castle Point vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and stays individually. Better still, you can customize your Castle Point trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
How to plan a trip to Castle Point?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Castle Point.
  2. Budget wisely: In addition to the price of your stay, you should consider other expenses. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Castle Point.
  3. Decide how long to go away for: Now that you're up to speed on Castle Point, you can work out the perfect length of your break. Create a draft itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized Castle Point vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.