Castle Point Vacations from $438

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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.
Harpoon House

Harpoon House

3 out of 5
Save 100% on your flight
per person
Oct 5 - Oct 8
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
8.4/10 Very Good! (124 reviews)
Our room had a particular closeness to the Main Street and restaurant which made for lot of noise until about 2 am. The parking area was separated from the main hotel door by a drainage area with nowhere to cross except through the mud. The piles of chairs around the foul smelling dumpster in the parking area did not feel welcoming. Room was quite spacious and clean. The bed was comfortable. Nothing can be done concerning the noise but the parking area would be easy to fix with a bit of attention.

Reviewed on Jul 20, 2025

Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.6/10 Exceptional! (8 reviews)
The place and amenities were really nice. The only bad thing was the bathroom got nasty really quick so for me the shared bathrooms won’t work. But they do have private bathroom rooms. Other than the dirty bathrooms not getting cleaned enough everything was great, location and space.

Reviewed on Jun 25, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (544 reviews)
We stayed here for an overnight for a girls trip with my 8yr old daughter, we had the best time. We will be back!

Reviewed on Jul 30, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
Save 100% on your flight
per person
Sep 26 - Sep 29
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (492 reviews)
My only issue was the bed pillows need updating. They weren’t very comfortable, felt old and were faded.

Reviewed on Jul 22, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Save 100% on your flight
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,273 reviews)
Right across from the subway entrance, a Starbucks, and next to a Walgreens. Down the street, McD’s, Subway, Panda, CVS. Blocks away from Rockefeller Center. A block away from police and fire, felt safe the whole time. The property was modern and clean. We used the microwave in the lobby, our room had a fridge. Normal room size and not NY size, bed was comfortable and room was quiet! Definitely want to stay here again on the next trip.

Reviewed on Aug 3, 2025

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Discover the most popular places to visit in Castle Point

Poughkeepsie Galleria

4/5(6 reviews)

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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $154 total per night from Aug 25 to Aug 26
$154 total
Aug 25 - Aug 26
Total includes taxes and fees
8.2/10 Very Good! (1,001 reviews)
"Great price. Wonderful location. Will be back!"

Reviewed on Jul 31, 2025

Overlook Lodge at Bear Mountain
Wingate by Wyndham Fishkill

Wingate by Wyndham Fishkill

3 out of 5
20 Schuyler Blvd, Fishkill, NY
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $118 total per night from Aug 17 to Aug 18
$118 total
Aug 17 - Aug 18
Total includes taxes and fees
7.4/10 Good! (458 reviews)
"Would go back"

Reviewed on Jul 30, 2025

Wingate by Wyndham Fishkill
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

2.5 out of 5
60 Centre Dr, Central Valley, NY
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $156 total per night from Sep 2 to Sep 3
$156 total
Sep 2 - Sep 3
Total includes taxes and fees
9/10 Wonderful! (1,004 reviews)
"The room was in quiet area no kids making noise thank you will request same area next time I visit"

Reviewed on Aug 3, 2025

Hampton Inn Harriman Woodbury
See all 773 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.

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Frequently asked questions

How much does a Castle Point vacation package cost?
You'll find cheap prices from $438 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.