Castle Point Vacations from $701

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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.

The Latest Castle Point vacation packages

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

Radio Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,355, price is now $701 per person
$701
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.6/10 Excellent! (2,498 reviews)
Very amazing hospitality, good people not far from all the action! Peaceful!

Reviewed on Jul 19, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
Price was $3,392, price is now $1,955 per person
$1,955
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (685 reviews)

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $3,366, price is now $2,001 per person
$2,001
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,006 reviews)

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,857, price is now $1,111 per person
$1,111
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.6/10 Exceptional! (1,617 reviews)
Clean and quiet room with helpful staff.

Reviewed on Jul 19, 2026

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $1,204, price is now $722 per person
$722
per person
Sep 21 - Sep 26
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (659 reviews)

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Castle Point 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
$110 nightly
The price is $128 total per night from Aug 2 to Aug 3
$128 total
Aug 2 - Aug 3
Total with taxes and fees
Hyatt Place Poughkeepsie / Hudson Valley
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $103 total per night from Aug 11 to Aug 12
$103 total
Aug 11 - Aug 12
Total with taxes and fees
8.4/10 Very Good! (176 reviews)
"The room was fairly clean. I found a hair in the bedsheets. They do not clean the room every day. I needed extra towels and it took me hunting down housekeeping to get it. The bathroom is too small. The bathroom sink is in the room not the bathroom. Breakfast was good. Bagels were good after toasting. ..."

Reviewed on Jul 19, 2026

Spark by Hilton Fishkill
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
$142 nightly
The price is $175 total per night from Jul 20 to Jul 21
$175 total
Jul 20 - Jul 21
Total with taxes and fees
8.4/10 Very Good! (1,013 reviews)
"Wonderful old feeling with many available activities. Front desk staff was amazing."

Reviewed on Jul 19, 2026

Overlook Lodge at Bear Mountain
See all 771 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.

Find the Best Castle Point Vacation Packages

Castle Point Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Top Sights
Fun Central, Dutchess Stadium and Bowdoin Park

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Frequently asked questions

How much does a Castle Point vacation package cost?
You'll find cheap prices from $701 on Expedia for your Castle Point escape. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Castle Point costs.
What are the cheapest months to go to Castle Point?
December, January and February are the best times to search for cheap Castle Point vacation packages. Choosing to travel in less busy periods means you can typically find better prices on accommodations and flights.
How many days is enough for Castle Point?
With a well-planned itinerary, you can easily hit the main Castle Point attractions in a handful of days. But if you want to venture off the beaten track or take day trips, think about booking your Castle Point vacation for longer.
How to find the best Castle Point package deals?
Use Expedia's filters to help you find some terrific Castle Point package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Castle Point package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Castle Point vacation as a package?
You can enjoy significant savings on your next Castle Point break by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to see some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Castle Point?
Secure incredible discounts by reserving your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Castle Point break.
Does Expedia offer Book Now, Pay Later Castle Point vacation packages?
Your Castle Point trip is meant to be a relaxing escape from your busy life, not a source of money-related stress. So to allow you a little more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.