Castle Point Vacations from $329

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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.
Newark Liberty International Airport Marriott

Newark Liberty International Airport Marriott

4 out of 5
Save 100% on your flight
Price was $605, price is now $329 per person
$329
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (1,020 reviews)
Very small room and beds

Reviewed on Oct 26, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $1,747, price is now $943 per person
$943
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Miami (MIA) to New York (NYC)
8.4/10 Very Good! (579 reviews)
Another amazing stay, even during a nor’easter. The staff did their best to still make the stay as enjoyable as it could have been with most things closed in the area. They were also kind enough to put us in the same room we had last time, which is our favorite thing about the Soundview and our trips out east. The view from our deck and the cute small things they have for dogs will keep us coming back. Thank you for another memorable trip.

Reviewed on Oct 26, 2025

Hotel Seville Nomad, in the Unbound Collection by Hyatt

Hotel Seville Nomad, in the Unbound Collection by Hyatt

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,420, price is now $770 per person
$770
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,140 reviews)
Great! We love this place.

Reviewed on Oct 22, 2025

Harpoon House

Harpoon House

3 out of 5
Price was $1,579, price is now $886 per person
$886
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Miami (MIA) to New York (NYC)
8.4/10 Very Good! (143 reviews)
We were looking for a quick overnight in the East End, and the Harpoon House exceeded our expectations in every way. The room was spacious (a suite!) and well-appointed, blending the charm of the original 1648 (!) building with modern amenities and furnishings. We didn't take advantage of the on-property restaurant (formerly Blu Mar), but the menu - by acclaimed chef Rocco DiSpirito - looked excellent, if a bit pricey. Location was ideal, within easy walking distance of all Main Street shops and restaurants, and less than a mile to the beach. And, although things were a bit quieter than in the height of summer - not a bad thing! - we loved being out there for the fall harvest season, with wineries and farms in full swing. All-in-all, our stay at the Harpoon House made for a perfect fall weekend in the Hamptons - highly recommended.

Reviewed on Oct 20, 2025

Thompson Central Park New York, by Hyatt

Thompson Central Park New York, by Hyatt

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,948, price is now $1,115 per person
$1,115
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,106 reviews)
Love the whole hotel.

Reviewed on Oct 25, 2025

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Discover the most popular places to visit in Castle Point

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

Castle Point Hotel Deals

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
$109 nightly
The price is $129 total per night from Oct 27 to Oct 28
$129 total
Oct 27 - Oct 28
Total with taxes and fees
7/10 Good! (638 reviews)
Location was good and staff was friendly

Reviewed on Oct 23, 2025

The Crossroads Hotel, Newburgh
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
$110 nightly
The price is $128 total per night from Nov 2 to Nov 3
$128 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (1,008 reviews)
We had some issues with ants in the room, around the coffee bar. We reported it and were quickly given another room. Staff was helpful and friendly.

Reviewed on Oct 24, 2025

Hampton Inn & Suites Poughkeepsie
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
2702 Main St, Gardiner, NY
$1,150 nightly
The price is $1,288 total per night from Nov 25 to Nov 26
$1,288 total
Nov 25 - Nov 26
Total with taxes and fees
9.4/10 Exceptional! (54 reviews)
Where do I start…. Everything was clean and felt so luxurious. The staff was unbelievably polite, kind, and caring. The grounds are beautiful. The spa is perfect. The amenities are top tier. The food is TRULY farm to table (you can go see the farm on a 5 minute walk if you need proof). Just the perfect ...

Reviewed on Sep 16, 2025

Wildflower Farms, Auberge Collection
See all 742 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 $329 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.